From dea73a7938b3761ec3aaf7b8ae2cbfbcd176e322 Mon Sep 17 00:00:00 2001
From: =?UTF-8?q?Oliver=20G=C3=BCnther?= <mail@oliverguenther.de>
Date: Mon, 11 May 2026 21:27:00 +0200
Subject: [PATCH 1/3] Move all custom actions into an automations namespace

---
 .../index_component.rb}                       |  18 ++-
 .../row_component.rb                          |  31 +++-
 .../cu_contract.rb                            |  21 +--
 .../execute_contract.rb                       |  16 +-
 ...ontroller.rb => automations_controller.rb} |  43 +++---
 .../{custom_action.rb => automation.rb}       |  61 ++++++--
 .../actions/assigned_to.rb                    |   4 +-
 .../actions/base.rb                           |   2 +-
 .../actions/custom_field.rb                   |  28 ++--
 .../actions/date.rb                           |   4 +-
 .../actions/done_ratio.rb                     |   4 +-
 .../actions/due_date.rb                       |   4 +-
 .../actions/estimated_hours.rb                |   4 +-
 .../actions/inexistent.rb                     |   2 +-
 .../actions/notify.rb                         |   4 +-
 .../actions/priority.rb                       |   4 +-
 .../actions/project.rb                        |   4 +-
 .../actions/responsible.rb                    |   4 +-
 .../actions/serializer.rb                     |   6 +-
 .../actions/start_date.rb                     |   4 +-
 .../actions/status.rb                         |   4 +-
 .../actions/strategies/associated.rb          |   6 +-
 .../strategies/associated_custom_field.rb     |   6 +-
 .../actions/strategies/boolean.rb             |  32 +++-
 .../actions/strategies/custom_field.rb        |   2 +-
 .../actions/strategies/date.rb                |   4 +-
 .../actions/strategies/date_property.rb       |   4 +-
 .../actions/strategies/float.rb               |   4 +-
 .../actions/strategies/integer.rb             |   6 +-
 .../actions/strategies/link.rb                |   4 +-
 .../actions/strategies/me_associated.rb       |   6 +-
 .../actions/strategies/string.rb              |   4 +-
 .../actions/strategies/text.rb                |   4 +-
 .../actions/strategies/user_custom_field.rb   |   6 +-
 .../actions/strategies/validate_in_range.rb   |   2 +-
 .../actions/strategies/values_to_string.rb    |   2 +-
 .../actions/type.rb                           |   4 +-
 .../conditions/base.rb                        |  40 +++--
 .../conditions/inexistent.rb                  |   2 +-
 .../conditions/project.rb                     |   2 +-
 .../conditions/role.rb                        |  12 +-
 .../conditions/status.rb                      |   2 +-
 .../conditions/type.rb                        |   2 +-
 .../register.rb                               |  36 ++---
 app/models/automations/triggers/base.rb       |  41 +++++
 .../models/automations/triggers/manual.rb     |  11 +-
 .../validate_allowed_value.rb                 |  30 +++-
 .../values_to_integer.rb                      |   2 +-
 app/models/permitted_params.rb                |  19 +--
 app/models/work_package.rb                    |   2 +-
 .../{custom_actioned.rb => automatable.rb}    |  17 +-
 app/models/work_package_custom_field.rb       |   2 +-
 .../base_service.rb                           |  37 +++--
 .../create_service.rb                         |   7 +-
 .../update_service.rb                         |   3 +-
 .../update_work_package_service.rb            |  12 +-
 .../_form.html.erb                            | 145 +++++++++---------
 .../_trigger_fields_manual.html.erb           |  42 +++++
 .../edit.html.erb                             |  12 +-
 app/views/automations/index.html.erb          |  60 ++++++++
 .../new.html.erb                              |  12 +-
 app/views/custom_actions/index.html.erb       |  31 ----
 config/initializers/menus.rb                  |   6 +-
 config/locales/en.yml                         |  24 +++
 config/routes.rb                              |   2 +-
 ...8_convert_custom_actions_to_automations.rb | 115 ++++++++++++++
 .../custom_action_representer.rb              |   9 +-
 .../v3/custom_actions/custom_actions_api.rb   |   8 +-
 .../{custom_action.rb => automation.rb}       |  37 +++--
 .../work_package_eager_loading_wrapper.rb     |   2 +-
 .../cu_contract_spec.rb                       |  22 +--
 ...spec.rb => automations_controller_spec.rb} |  82 +++++-----
 spec/factories/automation_factory.rb          |  51 ++++++
 .../automations_link_value_spec.rb}           |  11 +-
 .../automations_me_value_spec.rb}             |  13 +-
 .../automations_spec.rb}                      | 126 ++++++++-------
 spec/helpers/no_results_helper_spec.rb        |   7 +-
 ...stom_action_representer_generation_spec.rb |  16 +-
 ...spec.rb => automation_integration_spec.rb} |  30 ++--
 .../work_package_representer_spec.rb          |  12 +-
 ...stom_action_spec.rb => automation_spec.rb} |  56 +++----
 .../actions/assigned_to_spec.rb               |  13 +-
 .../actions/custom_field_spec.rb              |  10 +-
 .../actions/date_spec.rb                      |  14 +-
 .../actions/done_ratio_spec.rb                |   4 +-
 .../actions/due_date_spec.rb                  |   4 +-
 .../actions/estimated_hours_spec.rb           |   4 +-
 .../actions/notify_spec.rb                    |  21 +--
 .../actions/priority_spec.rb                  |   6 +-
 .../actions/project_spec.rb                   |   6 +-
 .../actions/responsible_spec.rb               |  13 +-
 .../actions/start_date_spec.rb                |   4 +-
 .../actions/status_spec.rb                    |   6 +-
 .../strategies/user_custom_field_spec.rb      |  28 ++--
 .../actions/type_spec.rb                      |   2 +-
 .../conditions/project_spec.rb                |  22 ++-
 .../conditions/role_spec.rb                   |  28 ++--
 .../conditions/status_spec.rb                 |  22 ++-
 .../conditions/type_spec.rb                   |  18 +--
 .../shared_expectations.rb                    |  42 ++---
 spec/models/permitted_params_spec.rb          |   4 +-
 ...ec.rb => work_package_automations_spec.rb} |  30 ++--
 .../custom_actions/custom_actions_api_spec.rb |  24 ++-
 ...om_actions_spec.rb => automations_spec.rb} |  38 ++---
 .../update_service_spec.rb                    |  28 ++--
 .../update_work_package_service_spec.rb       |  38 +++--
 .../{custom_actions => automations}/edit.rb   |   9 +-
 .../{custom_actions => automations}/form.rb   |  20 ++-
 .../{custom_actions => automations}/index.rb  |  14 +-
 .../{custom_actions => automations}/new.rb    |   4 +-
 .../work_packages/abstract_work_package.rb    |  10 +-
 111 files changed, 1246 insertions(+), 818 deletions(-)
 rename app/components/{custom_actions/table_component.rb => automations/index_component.rb} (73%)
 rename app/components/{custom_actions => automations}/row_component.rb (71%)
 rename app/contracts/{custom_actions => automations}/cu_contract.rb (79%)
 rename app/contracts/{custom_actions => automations}/execute_contract.rb (79%)
 rename app/controllers/{custom_actions_controller.rb => automations_controller.rb} (61%)
 rename app/models/{custom_action.rb => automation.rb} (61%)
 rename app/models/{custom_actions => automations}/actions/assigned_to.rb (92%)
 rename app/models/{custom_actions => automations}/actions/base.rb (98%)
 rename app/models/{custom_actions => automations}/actions/custom_field.rb (79%)
 rename app/models/{custom_actions => automations}/actions/date.rb (92%)
 rename app/models/{custom_actions => automations}/actions/done_ratio.rb (92%)
 rename app/models/{custom_actions => automations}/actions/due_date.rb (90%)
 rename app/models/{custom_actions => automations}/actions/estimated_hours.rb (91%)
 rename app/models/{custom_actions => automations}/actions/inexistent.rb (95%)
 rename app/models/{custom_actions => automations}/actions/notify.rb (93%)
 rename app/models/{custom_actions => automations}/actions/priority.rb (91%)
 rename app/models/{custom_actions => automations}/actions/project.rb (92%)
 rename app/models/{custom_actions => automations}/actions/responsible.rb (92%)
 rename app/models/{custom_actions => automations}/actions/serializer.rb (93%)
 rename app/models/{custom_actions => automations}/actions/start_date.rb (90%)
 rename app/models/{custom_actions => automations}/actions/status.rb (91%)
 rename app/models/{custom_actions => automations}/actions/strategies/associated.rb (92%)
 rename app/models/{custom_actions => automations}/actions/strategies/associated_custom_field.rb (88%)
 rename app/models/{custom_actions => automations}/actions/strategies/boolean.rb (50%)
 rename app/models/{custom_actions => automations}/actions/strategies/custom_field.rb (96%)
 rename app/models/{custom_actions => automations}/actions/strategies/date.rb (96%)
 rename app/models/{custom_actions => automations}/actions/strategies/date_property.rb (92%)
 rename app/models/{custom_actions => automations}/actions/strategies/float.rb (92%)
 rename app/models/{custom_actions => automations}/actions/strategies/integer.rb (89%)
 rename app/models/{custom_actions => automations}/actions/strategies/link.rb (93%)
 rename app/models/{custom_actions => automations}/actions/strategies/me_associated.rb (92%)
 rename app/models/{custom_actions => automations}/actions/strategies/string.rb (92%)
 rename app/models/{custom_actions => automations}/actions/strategies/text.rb (92%)
 rename app/models/{custom_actions => automations}/actions/strategies/user_custom_field.rb (93%)
 rename app/models/{custom_actions => automations}/actions/strategies/validate_in_range.rb (97%)
 rename app/models/{custom_actions => automations}/actions/strategies/values_to_string.rb (96%)
 rename app/models/{custom_actions => automations}/actions/type.rb (92%)
 rename app/models/{custom_actions => automations}/conditions/base.rb (76%)
 rename app/models/{custom_actions => automations}/conditions/inexistent.rb (94%)
 rename app/models/{custom_actions => automations}/conditions/project.rb (95%)
 rename app/models/{custom_actions => automations}/conditions/role.rb (86%)
 rename app/models/{custom_actions => automations}/conditions/status.rb (94%)
 rename app/models/{custom_actions => automations}/conditions/type.rb (95%)
 rename app/models/{custom_actions => automations}/register.rb (64%)
 create mode 100644 app/models/automations/triggers/base.rb
 rename spec/factories/custom_action_factory.rb => app/models/automations/triggers/manual.rb (86%)
 rename app/models/{custom_actions => automations}/validate_allowed_value.rb (50%)
 rename app/models/{custom_actions => automations}/values_to_integer.rb (97%)
 rename app/models/work_package/{custom_actioned.rb => automatable.rb} (79%)
 rename app/services/{custom_actions => automations}/base_service.rb (75%)
 rename app/services/{custom_actions => automations}/create_service.rb (90%)
 rename app/services/{custom_actions => automations}/update_service.rb (95%)
 rename app/services/{custom_actions => automations}/update_work_package_service.rb (91%)
 rename app/views/{custom_actions => automations}/_form.html.erb (60%)
 create mode 100644 app/views/automations/_trigger_fields_manual.html.erb
 rename app/views/{custom_actions => automations}/edit.html.erb (83%)
 create mode 100644 app/views/automations/index.html.erb
 rename app/views/{custom_actions => automations}/new.html.erb (84%)
 delete mode 100644 app/views/custom_actions/index.html.erb
 create mode 100644 db/migrate/20260907113318_convert_custom_actions_to_automations.rb
 rename lib/api/v3/work_packages/eager_loading/{custom_action.rb => automation.rb} (61%)
 rename spec/contracts/{custom_actions => automations}/cu_contract_spec.rb (81%)
 rename spec/controllers/{custom_actions_controller_spec.rb => automations_controller_spec.rb} (85%)
 create mode 100644 spec/factories/automation_factory.rb
 rename spec/features/work_packages/{custom_actions/custom_actions_link_value_spec.rb => automations/automations_link_value_spec.rb} (88%)
 rename spec/features/work_packages/{custom_actions/custom_actions_me_value_spec.rb => automations/automations_me_value_spec.rb} (85%)
 rename spec/features/work_packages/{custom_actions/custom_actions_spec.rb => automations/automations_spec.rb} (83%)
 rename spec/lib/api/v3/work_packages/eager_loading/{custom_actions_integration_spec.rb => automation_integration_spec.rb} (69%)
 rename spec/models/{custom_action_spec.rb => automation_spec.rb} (76%)
 rename spec/models/{custom_actions => automations}/actions/assigned_to_spec.rb (87%)
 rename spec/models/{custom_actions => automations}/actions/custom_field_spec.rb (98%)
 rename spec/models/{custom_actions => automations}/actions/date_spec.rb (88%)
 rename spec/models/{custom_actions => automations}/actions/done_ratio_spec.rb (96%)
 rename spec/models/{custom_actions => automations}/actions/due_date_spec.rb (95%)
 rename spec/models/{custom_actions => automations}/actions/estimated_hours_spec.rb (95%)
 rename spec/models/{custom_actions => automations}/actions/notify_spec.rb (81%)
 rename spec/models/{custom_actions => automations}/actions/priority_spec.rb (92%)
 rename spec/models/{custom_actions => automations}/actions/project_spec.rb (92%)
 rename spec/models/{custom_actions => automations}/actions/responsible_spec.rb (87%)
 rename spec/models/{custom_actions => automations}/actions/start_date_spec.rb (95%)
 rename spec/models/{custom_actions => automations}/actions/status_spec.rb (92%)
 rename spec/models/{custom_actions => automations}/actions/strategies/user_custom_field_spec.rb (88%)
 rename spec/models/{custom_actions => automations}/actions/type_spec.rb (97%)
 rename spec/models/{custom_actions => automations}/conditions/project_spec.rb (79%)
 rename spec/models/{custom_actions => automations}/conditions/role_spec.rb (77%)
 rename spec/models/{custom_actions => automations}/conditions/status_spec.rb (80%)
 rename spec/models/{custom_actions => automations}/conditions/type_spec.rb (84%)
 rename spec/models/{custom_actions => automations}/shared_expectations.rb (92%)
 rename spec/models/work_package/{work_package_custom_actions_spec.rb => work_package_automations_spec.rb} (80%)
 rename spec/routing/{custom_actions_spec.rb => automations_spec.rb} (61%)
 rename spec/services/{custom_actions => automations}/update_service_spec.rb (86%)
 rename spec/services/{custom_actions => automations}/update_work_package_service_spec.rb (84%)
 rename spec/support/pages/admin/{custom_actions => automations}/edit.rb (90%)
 rename spec/support/pages/admin/{custom_actions => automations}/form.rb (87%)
 rename spec/support/pages/admin/{custom_actions => automations}/index.rb (89%)
 rename spec/support/pages/admin/{custom_actions => automations}/new.rb (96%)

diff --git a/app/components/custom_actions/table_component.rb b/app/components/automations/index_component.rb
similarity index 73%
rename from app/components/custom_actions/table_component.rb
rename to app/components/automations/index_component.rb
index 324f8f7dc576..fdaa9b214d01 100644
--- a/app/components/custom_actions/table_component.rb
+++ b/app/components/automations/index_component.rb
@@ -28,14 +28,16 @@
 # See COPYRIGHT and LICENSE files for more details.
 #++
 
-module CustomActions
-  class TableComponent < ::TableComponent
-    columns :name, :description, :sort
+module Automations
+  class IndexComponent < ::TableComponent
+    columns :name, :triggers, :conditions, :actions, :sort
 
     def headers
       [
-        ["name", { caption: CustomAction.human_attribute_name(:name) }],
-        ["description", { caption: CustomAction.human_attribute_name(:description) }],
+        ["name", { caption: Automation.human_attribute_name(:name) }],
+        ["triggers", { caption: I18n.t("automations.triggers.name") }],
+        ["conditions", { caption: I18n.t("automations.conditions") }],
+        ["actions", { caption: I18n.t("automations.actions.name") }],
         ["sort", { caption: I18n.t(:label_sort) }]
       ]
     end
@@ -45,10 +47,10 @@ def sortable?
     end
 
     def inline_create_link
-      link_to new_custom_action_path,
-              aria: { label: t("custom_actions.new") },
+      link_to new_automation_path,
+              aria: { label: t("automations.new") },
               class: "wp-inline-create--add-link",
-              title: t("custom_actions.new") do
+              title: t("automations.new") do
         helpers.op_icon("icon icon-add")
       end
     end
diff --git a/app/components/custom_actions/row_component.rb b/app/components/automations/row_component.rb
similarity index 71%
rename from app/components/custom_actions/row_component.rb
rename to app/components/automations/row_component.rb
index 2f3f065f605a..5bd09372d89a 100644
--- a/app/components/custom_actions/row_component.rb
+++ b/app/components/automations/row_component.rb
@@ -28,20 +28,37 @@
 # See COPYRIGHT and LICENSE files for more details.
 #++
 
-module CustomActions
+module Automations
   class RowComponent < ::RowComponent
-    def action
+    def automation
       row
     end
 
     def name
-      link_to action.name, edit_custom_action_path(action)
+      link_to automation.name, edit_automation_path(automation)
     end
 
-    delegate :description, to: :action
+    def triggers
+      automation.triggers.map do |trigger|
+        case trigger
+        when Automations::Triggers::Manual
+          I18n.t("automations.triggers.manual.label")
+        else
+          trigger.type.demodulize
+        end
+      end.join(", ")
+    end
+
+    def conditions
+      automation.conditions.map(&:human_name).join(", ")
+    end
+
+    def actions
+      automation.actions.map(&:human_name).join(", ")
+    end
 
     def sort
-      helpers.reorder_links("custom_action", { action: "update", id: action }, method: :put)
+      helpers.reorder_links("automation", { action: "update", id: automation }, method: :put)
     end
 
     def button_links
@@ -54,7 +71,7 @@ def button_links
     def edit_link
       link_to(
         helpers.op_icon("icon icon-edit"),
-        helpers.edit_custom_action_path(action),
+        helpers.edit_automation_path(automation),
         title: t(:button_edit)
       )
     end
@@ -62,7 +79,7 @@ def edit_link
     def delete_link
       link_to(
         helpers.op_icon("icon icon-delete"),
-        helpers.custom_action_path(action),
+        helpers.automation_path(automation),
         data: {
           turbo_method: :delete,
           turbo_confirm: I18n.t(:text_are_you_sure)
diff --git a/app/contracts/custom_actions/cu_contract.rb b/app/contracts/automations/cu_contract.rb
similarity index 79%
rename from app/contracts/custom_actions/cu_contract.rb
rename to app/contracts/automations/cu_contract.rb
index d9a479bbf9fb..69801603a09d 100644
--- a/app/contracts/custom_actions/cu_contract.rb
+++ b/app/contracts/automations/cu_contract.rb
@@ -30,33 +30,22 @@
 
 require "model_contract"
 
-# Contract for create (c) and update (u)
-module CustomActions
+module Automations
   class CuContract < ::ModelContract
     def self.model
-      CustomAction
-    end
-
-    def initialize(model, user = nil)
-      super
+      Automation
     end
 
     attribute :name
     attribute :description
 
     attribute :actions do
-      if model.actions.empty?
-        errors.add :actions, :empty
-      end
-      model.actions.each do |action|
-        action.validate(errors)
-      end
+      errors.add(:actions, :empty) if model.actions.empty?
+      model.actions.each { |action| action.validate(errors) }
     end
 
     attribute :conditions do
-      model.conditions.each do |condition|
-        condition.validate(errors)
-      end
+      model.conditions.each { |condition| condition.validate(errors) }
     end
   end
 end
diff --git a/app/contracts/custom_actions/execute_contract.rb b/app/contracts/automations/execute_contract.rb
similarity index 79%
rename from app/contracts/custom_actions/execute_contract.rb
rename to app/contracts/automations/execute_contract.rb
index 8f327dd78062..4252e0fd283c 100644
--- a/app/contracts/custom_actions/execute_contract.rb
+++ b/app/contracts/automations/execute_contract.rb
@@ -28,35 +28,31 @@
 # See COPYRIGHT and LICENSE files for more details.
 #++
 
-module CustomActions
+module Automations
   class ExecuteContract < BaseContract
     property :lock_version
     property :work_package_id
 
     validates :work_package_id, presence: true
     validate :work_package_visible
-    validate :custom_action_conditions_fulfilled
+    validate :automation_conditions_fulfilled
 
     private
 
     def work_package_visible
       return unless model.work_package_id
 
-      unless WorkPackage.visible(user).where(id: model.work_package_id).exists?
-        errors.add(:work_package_id, :does_not_exist)
-      end
+      errors.add(:work_package_id, :does_not_exist) unless WorkPackage.visible(user).exists?(id: model.work_package_id)
     end
 
-    def custom_action_conditions_fulfilled
+    def automation_conditions_fulfilled
       return unless model.work_package_id
-      return unless options[:custom_action]
+      return unless options[:automation]
 
       work_package = WorkPackage.visible(user).find_by(id: model.work_package_id)
       return unless work_package
 
-      unless options[:custom_action].conditions_fulfilled?(work_package, user)
-        errors.add(:base, :error_unauthorized)
-      end
+      errors.add(:base, :error_unauthorized) unless options[:automation].conditions_fulfilled?(work_package, user)
     end
   end
 end
diff --git a/app/controllers/custom_actions_controller.rb b/app/controllers/automations_controller.rb
similarity index 61%
rename from app/controllers/custom_actions_controller.rb
rename to app/controllers/automations_controller.rb
index 62c766a58961..249754d5dbd0 100644
--- a/app/controllers/custom_actions_controller.rb
+++ b/app/controllers/automations_controller.rb
@@ -28,75 +28,72 @@
 # See COPYRIGHT and LICENSE files for more details.
 #++
 
-class CustomActionsController < ApplicationController
+class AutomationsController < ApplicationController
   before_action :require_admin
 
   guard_enterprise_feature(:custom_actions, only: %i[new create edit update]) do
     redirect_to action: :index
   end
 
-  before_action :find_custom_action, only: %i(edit update destroy)
-  before_action :pad_params, only: %i(create update)
+  before_action :find_automation, only: %i[edit update destroy]
+  before_action :pad_params, only: %i[create update]
 
   layout "admin"
 
   def index
-    @custom_actions = CustomAction.order_by_position
+    @automations = Automation.order_by_position.includes(:triggers)
   end
 
   def new
-    @custom_action = CustomAction.new
+    @automation = Automation.new
+    @automation.triggers.build(type: "Automations::Triggers::Manual")
   end
 
   def edit; end
 
   def create
-    CustomActions::CreateService
+    Automations::CreateService
       .new(user: current_user)
-      .call(attributes: permitted_params.custom_action.to_h,
+      .call(attributes: permitted_params.automation.to_h,
             &index_or_render(:new))
   end
 
   def update
-    CustomActions::UpdateService
-      .new(action: @custom_action, user: current_user)
-      .call(attributes: permitted_params.custom_action.to_h,
+    Automations::UpdateService
+      .new(action: @automation, user: current_user)
+      .call(attributes: permitted_params.automation.to_h,
             &index_or_render(:edit))
   end
 
   def destroy
-    @custom_action.destroy
+    @automation.destroy!
 
-    redirect_to custom_actions_path, status: :see_other
+    redirect_to automations_path, status: :see_other
   end
 
   private
 
-  def find_custom_action
-    @custom_action = CustomAction.find(params[:id])
+  def find_automation
+    @automation = Automation.find(params.expect(:id))
   end
 
   def index_or_render(render_action)
     ->(call) {
       call.on_success do
-        redirect_to custom_actions_path, status: :see_other
+        redirect_to automations_path, status: :see_other
       end
 
       call.on_failure do
-        @custom_action = call.result
+        @automation = call.result
         render action: render_action, status: :unprocessable_entity
       end
     }
   end
 
-  # If no action/condition is set in the view, the
-  # actions/conditions already existing on a custom action should be removed.
-  # But because it is not feasible to have an empty and hidden hash object in a form
-  # we have to pad the params here.
   def pad_params
-    return if !params[:custom_action] || params[:custom_action][:move_to]
+    return if !params[:automation] || params[:automation][:move_to]
 
-    params[:custom_action][:conditions] ||= {}
-    params[:custom_action][:actions] ||= {}
+    params[:automation][:conditions] ||= {}
+    params[:automation][:actions] ||= {}
   end
 end
diff --git a/app/models/custom_action.rb b/app/models/automation.rb
similarity index 61%
rename from app/models/custom_action.rb
rename to app/models/automation.rb
index c37d6ddb831f..cae2ddf36ef0 100644
--- a/app/models/custom_action.rb
+++ b/app/models/automation.rb
@@ -28,13 +28,28 @@
 # See COPYRIGHT and LICENSE files for more details.
 #++
 
-class CustomAction < ApplicationRecord
+class Automation < ApplicationRecord
   validates :name, length: { maximum: 255, minimum: 1 }
-  serialize :actions, coder: CustomActions::Actions::Serializer
-  has_and_belongs_to_many :status_conditions, class_name: "Status"
-  has_and_belongs_to_many :role_conditions, class_name: "Role"
-  has_and_belongs_to_many :type_conditions, class_name: "Type"
-  has_and_belongs_to_many :project_conditions, class_name: "Project"
+  validate :must_have_at_least_one_trigger
+  validate :must_not_have_more_than_one_manual_trigger
+
+  serialize :actions, coder: Automations::Actions::Serializer
+  before_validation :ensure_manual_trigger
+
+  # This code was moved from custom actions and it's decisions unchanged
+  # rubocop:disable Rails/HasAndBelongsToMany
+  has_and_belongs_to_many :status_conditions, class_name: "Status", join_table: :automations_statuses
+  has_and_belongs_to_many :role_conditions, class_name: "Role", join_table: :automations_roles
+  has_and_belongs_to_many :type_conditions, class_name: "Type", join_table: :automations_types
+  has_and_belongs_to_many :project_conditions, class_name: "Project", join_table: :automations_projects
+  # rubocop:enable Rails/HasAndBelongsToMany
+
+  has_many :triggers,
+           -> { order(:position, :id) },
+           class_name: "Automations::Triggers::Base",
+           dependent: :destroy,
+           inverse_of: :automation
+  accepts_nested_attributes_for :triggers
 
   after_save :persist_conditions
 
@@ -43,19 +58,18 @@ class CustomAction < ApplicationRecord
 
   acts_as_list
 
+  scope :with_manual_trigger, -> {
+    joins(:triggers).where(automation_triggers: { type: "Automations::Triggers::Manual" }).distinct
+  }
+
   def initialize(*args)
     ret = super
-
-    if actions.nil?
-      self.actions = []
-    end
-
+    self.actions ||= []
     ret
   end
 
   def reload(*args)
     @conditions = nil
-
     super
   end
 
@@ -77,16 +91,14 @@ def all_actions
   end
 
   def available_actions
-    ::CustomActions::Register.actions.map(&:all).flatten
+    ::Automations::Register.actions.map(&:all).flatten
   end
 
   def all_conditions
     all_of(available_conditions, conditions)
   end
 
-  def available_conditions
-    self.class.available_conditions
-  end
+  delegate :available_conditions, to: :class
 
   def conditions
     @conditions ||= available_conditions.filter_map do |condition_class|
@@ -104,11 +116,17 @@ def conditions_fulfilled?(work_package, user)
   end
 
   def self.available_conditions
-    ::CustomActions::Register.conditions
+    ::Automations::Register.conditions
   end
 
   private
 
+  def ensure_manual_trigger
+    return unless triggers.reject(&:marked_for_destruction?).empty?
+
+    triggers.build(type: "Automations::Triggers::Manual", options: { button_label: name })
+  end
+
   def all_of(availables, actual)
     availables.map do |available|
       existing = actual.detect { |a| a.key == available.key }
@@ -124,4 +142,13 @@ def persist_conditions
       condition_class.setter(self, condition)
     end
   end
+
+  def must_have_at_least_one_trigger
+    errors.add(:triggers, :blank) if triggers.reject(&:marked_for_destruction?).empty?
+  end
+
+  def must_not_have_more_than_one_manual_trigger
+    manual_triggers = triggers.reject(&:marked_for_destruction?).count { |trigger| trigger.type == "Automations::Triggers::Manual" }
+    errors.add(:triggers, :invalid) if manual_triggers > 1
+  end
 end
diff --git a/app/models/custom_actions/actions/assigned_to.rb b/app/models/automations/actions/assigned_to.rb
similarity index 92%
rename from app/models/custom_actions/actions/assigned_to.rb
rename to app/models/automations/actions/assigned_to.rb
index 2d0655e161be..87923628d76b 100644
--- a/app/models/custom_actions/actions/assigned_to.rb
+++ b/app/models/automations/actions/assigned_to.rb
@@ -28,8 +28,8 @@
 # See COPYRIGHT and LICENSE files for more details.
 #++
 
-class CustomActions::Actions::AssignedTo < CustomActions::Actions::Base
-  include CustomActions::Actions::Strategies::MeAssociated
+class Automations::Actions::AssignedTo < Automations::Actions::Base
+  include Automations::Actions::Strategies::MeAssociated
 
   def self.key
     :assigned_to
diff --git a/app/models/custom_actions/actions/base.rb b/app/models/automations/actions/base.rb
similarity index 98%
rename from app/models/custom_actions/actions/base.rb
rename to app/models/automations/actions/base.rb
index 3b131d6f80dc..ea78ba237067 100644
--- a/app/models/custom_actions/actions/base.rb
+++ b/app/models/automations/actions/base.rb
@@ -28,7 +28,7 @@
 # See COPYRIGHT and LICENSE files for more details.
 #++
 
-class CustomActions::Actions::Base
+class Automations::Actions::Base
   attr_reader :values
 
   DEFAULT_PRIORITY = 100
diff --git a/app/models/custom_actions/actions/custom_field.rb b/app/models/automations/actions/custom_field.rb
similarity index 79%
rename from app/models/custom_actions/actions/custom_field.rb
rename to app/models/automations/actions/custom_field.rb
index dd796273c4fc..1872cac30125 100644
--- a/app/models/custom_actions/actions/custom_field.rb
+++ b/app/models/automations/actions/custom_field.rb
@@ -28,7 +28,7 @@
 # See COPYRIGHT and LICENSE files for more details.
 #++
 
-class CustomActions::Actions::CustomField < CustomActions::Actions::Base
+class Automations::Actions::CustomField < Automations::Actions::Base
   class << self
     def key
       custom_field.attribute_name.to_sym
@@ -40,7 +40,7 @@ def custom_field
 
     def all
       WorkPackageCustomField
-        .usable_as_custom_action
+        .usable_as_automation
         .map do |cf|
           create_subclass(cf)
         end
@@ -57,7 +57,7 @@ def for(key)
     private
 
     def create_subclass(custom_field)
-      klass = Class.new(CustomActions::Actions::CustomField)
+      klass = Class.new(Automations::Actions::CustomField)
       klass.define_singleton_method(:custom_field) do
         custom_field
       end
@@ -69,30 +69,28 @@ def create_subclass(custom_field)
     def strategy(custom_field)
       case custom_field.field_format
       when "string"
-        CustomActions::Actions::Strategies::String
+        Automations::Actions::Strategies::String
       when "text"
-        CustomActions::Actions::Strategies::Text
+        Automations::Actions::Strategies::Text
       when "link"
-        CustomActions::Actions::Strategies::Link
+        Automations::Actions::Strategies::Link
       when "int"
-        CustomActions::Actions::Strategies::Integer
+        Automations::Actions::Strategies::Integer
       when "float"
-        CustomActions::Actions::Strategies::Float
+        Automations::Actions::Strategies::Float
       when "date"
-        CustomActions::Actions::Strategies::Date
+        Automations::Actions::Strategies::Date
       when "bool"
-        CustomActions::Actions::Strategies::Boolean
+        Automations::Actions::Strategies::Boolean
       when "user"
-        CustomActions::Actions::Strategies::UserCustomField
+        Automations::Actions::Strategies::UserCustomField
       when "list", "version"
-        CustomActions::Actions::Strategies::AssociatedCustomField
+        Automations::Actions::Strategies::AssociatedCustomField
       end
     end
   end
 
-  def custom_field
-    self.class.custom_field
-  end
+  delegate :custom_field, to: :class
 
   def human_name
     custom_field.name
diff --git a/app/models/custom_actions/actions/date.rb b/app/models/automations/actions/date.rb
similarity index 92%
rename from app/models/custom_actions/actions/date.rb
rename to app/models/automations/actions/date.rb
index 7e4f3bee3802..571788b33137 100644
--- a/app/models/custom_actions/actions/date.rb
+++ b/app/models/automations/actions/date.rb
@@ -28,8 +28,8 @@
 # See COPYRIGHT and LICENSE files for more details.
 #++
 
-class CustomActions::Actions::Date < CustomActions::Actions::Base
-  include CustomActions::Actions::Strategies::Date
+class Automations::Actions::Date < Automations::Actions::Base
+  include Automations::Actions::Strategies::Date
 
   def self.key
     :date
diff --git a/app/models/custom_actions/actions/done_ratio.rb b/app/models/automations/actions/done_ratio.rb
similarity index 92%
rename from app/models/custom_actions/actions/done_ratio.rb
rename to app/models/automations/actions/done_ratio.rb
index c885bb79e4bc..d51ecec36b95 100644
--- a/app/models/custom_actions/actions/done_ratio.rb
+++ b/app/models/automations/actions/done_ratio.rb
@@ -28,8 +28,8 @@
 # See COPYRIGHT and LICENSE files for more details.
 #++
 
-class CustomActions::Actions::DoneRatio < CustomActions::Actions::Base
-  include CustomActions::Actions::Strategies::Integer
+class Automations::Actions::DoneRatio < Automations::Actions::Base
+  include Automations::Actions::Strategies::Integer
 
   def self.key
     :done_ratio
diff --git a/app/models/custom_actions/actions/due_date.rb b/app/models/automations/actions/due_date.rb
similarity index 90%
rename from app/models/custom_actions/actions/due_date.rb
rename to app/models/automations/actions/due_date.rb
index e0836b1f032d..658e346291df 100644
--- a/app/models/custom_actions/actions/due_date.rb
+++ b/app/models/automations/actions/due_date.rb
@@ -28,8 +28,8 @@
 # See COPYRIGHT and LICENSE files for more details.
 #++
 
-class CustomActions::Actions::DueDate < CustomActions::Actions::Base
-  include CustomActions::Actions::Strategies::DateProperty
+class Automations::Actions::DueDate < Automations::Actions::Base
+  include Automations::Actions::Strategies::DateProperty
 
   def self.key
     :due_date
diff --git a/app/models/custom_actions/actions/estimated_hours.rb b/app/models/automations/actions/estimated_hours.rb
similarity index 91%
rename from app/models/custom_actions/actions/estimated_hours.rb
rename to app/models/automations/actions/estimated_hours.rb
index dcec6856db95..1c2b18e79b36 100644
--- a/app/models/custom_actions/actions/estimated_hours.rb
+++ b/app/models/automations/actions/estimated_hours.rb
@@ -28,8 +28,8 @@
 # See COPYRIGHT and LICENSE files for more details.
 #++
 
-class CustomActions::Actions::EstimatedHours < CustomActions::Actions::Base
-  include CustomActions::Actions::Strategies::Float
+class Automations::Actions::EstimatedHours < Automations::Actions::Base
+  include Automations::Actions::Strategies::Float
 
   def self.key
     :estimated_hours
diff --git a/app/models/custom_actions/actions/inexistent.rb b/app/models/automations/actions/inexistent.rb
similarity index 95%
rename from app/models/custom_actions/actions/inexistent.rb
rename to app/models/automations/actions/inexistent.rb
index 0be4c169ba7d..d5f8a757e7c3 100644
--- a/app/models/custom_actions/actions/inexistent.rb
+++ b/app/models/automations/actions/inexistent.rb
@@ -28,7 +28,7 @@
 # See COPYRIGHT and LICENSE files for more details.
 #++
 
-class CustomActions::Actions::Inexistent < CustomActions::Actions::Base
+class Automations::Actions::Inexistent < Automations::Actions::Base
   def self.key
     :inexistent
   end
diff --git a/app/models/custom_actions/actions/notify.rb b/app/models/automations/actions/notify.rb
similarity index 93%
rename from app/models/custom_actions/actions/notify.rb
rename to app/models/automations/actions/notify.rb
index e88a50edf5d0..dda26006920f 100644
--- a/app/models/custom_actions/actions/notify.rb
+++ b/app/models/automations/actions/notify.rb
@@ -28,8 +28,8 @@
 # See COPYRIGHT and LICENSE files for more details.
 #++
 
-class CustomActions::Actions::Notify < CustomActions::Actions::Base
-  include CustomActions::Actions::Strategies::Associated
+class Automations::Actions::Notify < Automations::Actions::Base
+  include Automations::Actions::Strategies::Associated
 
   def apply(work_package)
     comment = principals.where(id: values).map do |p|
diff --git a/app/models/custom_actions/actions/priority.rb b/app/models/automations/actions/priority.rb
similarity index 91%
rename from app/models/custom_actions/actions/priority.rb
rename to app/models/automations/actions/priority.rb
index 7826a99c87e0..97011b57fc26 100644
--- a/app/models/custom_actions/actions/priority.rb
+++ b/app/models/automations/actions/priority.rb
@@ -28,8 +28,8 @@
 # See COPYRIGHT and LICENSE files for more details.
 #++
 
-class CustomActions::Actions::Priority < CustomActions::Actions::Base
-  include CustomActions::Actions::Strategies::Associated
+class Automations::Actions::Priority < Automations::Actions::Base
+  include Automations::Actions::Strategies::Associated
 
   def associated
     IssuePriority
diff --git a/app/models/custom_actions/actions/project.rb b/app/models/automations/actions/project.rb
similarity index 92%
rename from app/models/custom_actions/actions/project.rb
rename to app/models/automations/actions/project.rb
index 5c893303fd08..c1d6f78ba9c5 100644
--- a/app/models/custom_actions/actions/project.rb
+++ b/app/models/automations/actions/project.rb
@@ -28,8 +28,8 @@
 # See COPYRIGHT and LICENSE files for more details.
 #++
 
-class CustomActions::Actions::Project < CustomActions::Actions::Base
-  include CustomActions::Actions::Strategies::Associated
+class Automations::Actions::Project < Automations::Actions::Base
+  include Automations::Actions::Strategies::Associated
 
   PRIORITY = 10
 
diff --git a/app/models/custom_actions/actions/responsible.rb b/app/models/automations/actions/responsible.rb
similarity index 92%
rename from app/models/custom_actions/actions/responsible.rb
rename to app/models/automations/actions/responsible.rb
index c0b8e59f09f2..c83d1531620b 100644
--- a/app/models/custom_actions/actions/responsible.rb
+++ b/app/models/automations/actions/responsible.rb
@@ -28,8 +28,8 @@
 # See COPYRIGHT and LICENSE files for more details.
 #++
 
-class CustomActions::Actions::Responsible < CustomActions::Actions::Base
-  include CustomActions::Actions::Strategies::MeAssociated
+class Automations::Actions::Responsible < Automations::Actions::Base
+  include Automations::Actions::Strategies::MeAssociated
 
   def type
     :user
diff --git a/app/models/custom_actions/actions/serializer.rb b/app/models/automations/actions/serializer.rb
similarity index 93%
rename from app/models/custom_actions/actions/serializer.rb
rename to app/models/automations/actions/serializer.rb
index 81ca8efab3e1..1905419e896b 100644
--- a/app/models/custom_actions/actions/serializer.rb
+++ b/app/models/automations/actions/serializer.rb
@@ -28,7 +28,7 @@
 # See COPYRIGHT and LICENSE files for more details.
 #++
 
-module CustomActions::Actions::Serializer
+module Automations::Actions::Serializer
   module_function
 
   def load(value)
@@ -39,13 +39,13 @@ def load(value)
       .filter_map do |key, values|
       klass = nil
 
-      CustomActions::Register
+      Automations::Register
         .actions
         .detect do |a|
         klass = a.for(key)
       end
 
-      klass ||= CustomActions::Actions::Inexistent
+      klass ||= Automations::Actions::Inexistent
 
       klass.new(values)
     end
diff --git a/app/models/custom_actions/actions/start_date.rb b/app/models/automations/actions/start_date.rb
similarity index 90%
rename from app/models/custom_actions/actions/start_date.rb
rename to app/models/automations/actions/start_date.rb
index 9d5fc185d48c..5fd880de18b2 100644
--- a/app/models/custom_actions/actions/start_date.rb
+++ b/app/models/automations/actions/start_date.rb
@@ -28,8 +28,8 @@
 # See COPYRIGHT and LICENSE files for more details.
 #++
 
-class CustomActions::Actions::StartDate < CustomActions::Actions::Base
-  include CustomActions::Actions::Strategies::DateProperty
+class Automations::Actions::StartDate < Automations::Actions::Base
+  include Automations::Actions::Strategies::DateProperty
 
   def self.key
     :start_date
diff --git a/app/models/custom_actions/actions/status.rb b/app/models/automations/actions/status.rb
similarity index 91%
rename from app/models/custom_actions/actions/status.rb
rename to app/models/automations/actions/status.rb
index 30a939d38130..e1942004e504 100644
--- a/app/models/custom_actions/actions/status.rb
+++ b/app/models/automations/actions/status.rb
@@ -28,8 +28,8 @@
 # See COPYRIGHT and LICENSE files for more details.
 #++
 
-class CustomActions::Actions::Status < CustomActions::Actions::Base
-  include CustomActions::Actions::Strategies::Associated
+class Automations::Actions::Status < Automations::Actions::Base
+  include Automations::Actions::Strategies::Associated
 
   def self.key
     :status
diff --git a/app/models/custom_actions/actions/strategies/associated.rb b/app/models/automations/actions/strategies/associated.rb
similarity index 92%
rename from app/models/custom_actions/actions/strategies/associated.rb
rename to app/models/automations/actions/strategies/associated.rb
index e608b67b6389..ffbeb2615ded 100644
--- a/app/models/custom_actions/actions/strategies/associated.rb
+++ b/app/models/automations/actions/strategies/associated.rb
@@ -28,9 +28,9 @@
 # See COPYRIGHT and LICENSE files for more details.
 #++
 
-module CustomActions::Actions::Strategies::Associated
-  include CustomActions::ValidateAllowedValue
-  include CustomActions::ValuesToInteger
+module Automations::Actions::Strategies::Associated
+  include Automations::ValidateAllowedValue
+  include Automations::ValuesToInteger
 
   def allowed_values
     @allowed_values ||= begin
diff --git a/app/models/custom_actions/actions/strategies/associated_custom_field.rb b/app/models/automations/actions/strategies/associated_custom_field.rb
similarity index 88%
rename from app/models/custom_actions/actions/strategies/associated_custom_field.rb
rename to app/models/automations/actions/strategies/associated_custom_field.rb
index 97ccda753dc9..ee731e0be06e 100644
--- a/app/models/custom_actions/actions/strategies/associated_custom_field.rb
+++ b/app/models/automations/actions/strategies/associated_custom_field.rb
@@ -28,9 +28,9 @@
 # See COPYRIGHT and LICENSE files for more details.
 #++
 
-module CustomActions::Actions::Strategies::AssociatedCustomField
-  include CustomActions::Actions::Strategies::Associated
-  include CustomActions::Actions::Strategies::CustomField
+module Automations::Actions::Strategies::AssociatedCustomField
+  include Automations::Actions::Strategies::Associated
+  include Automations::Actions::Strategies::CustomField
 
   def associated
     custom_field
diff --git a/app/models/custom_actions/actions/strategies/boolean.rb b/app/models/automations/actions/strategies/boolean.rb
similarity index 50%
rename from app/models/custom_actions/actions/strategies/boolean.rb
rename to app/models/automations/actions/strategies/boolean.rb
index 96ed10bbbbda..dc098d69513f 100644
--- a/app/models/custom_actions/actions/strategies/boolean.rb
+++ b/app/models/automations/actions/strategies/boolean.rb
@@ -1,5 +1,33 @@
 # frozen_string_literal: true
 
+#-- copyright
+# OpenProject is an open source project management software.
+# Copyright (C) the OpenProject GmbH
+#
+# This program is free software; you can redistribute it and/or
+# modify it under the terms of the GNU General Public License version 3.
+#
+# OpenProject is a fork of ChiliProject, which is a fork of Redmine. The copyright follows:
+# Copyright (C) 2006-2013 Jean-Philippe Lang
+# Copyright (C) 2010-2013 the ChiliProject Team
+#
+# This program is free software; you can redistribute it and/or
+# modify it under the terms of the GNU General Public License
+# as published by the Free Software Foundation; either version 2
+# of the License, or (at your option) any later version.
+#
+# This program is distributed in the hope that it will be useful,
+# but WITHOUT ANY WARRANTY; without even the implied warranty of
+# MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the
+# GNU General Public License for more details.
+#
+# You should have received a copy of the GNU General Public License
+# along with this program; if not, write to the Free Software
+# Foundation, Inc., 51 Franklin Street, Fifth Floor, Boston, MA  02110-1301, USA.
+#
+# See COPYRIGHT and LICENSE files for more details.
+#++
+
 # OpenProject is a fork of ChiliProject, which is a fork of Redmine. The copyright follows:
 # Copyright (C) 2006-2017 Jean-Philippe Lang
 # Copyright (C) 2010-2013 the ChiliProject Team
@@ -21,8 +49,8 @@
 # See COPYRIGHT and LICENSE files for more details.
 #++
 
-module CustomActions::Actions::Strategies::Boolean
-  include CustomActions::ValidateAllowedValue
+module Automations::Actions::Strategies::Boolean
+  include Automations::ValidateAllowedValue
 
   def allowed_values
     [
diff --git a/app/models/custom_actions/actions/strategies/custom_field.rb b/app/models/automations/actions/strategies/custom_field.rb
similarity index 96%
rename from app/models/custom_actions/actions/strategies/custom_field.rb
rename to app/models/automations/actions/strategies/custom_field.rb
index 3d9c2071f9d5..f9fbe832e283 100644
--- a/app/models/custom_actions/actions/strategies/custom_field.rb
+++ b/app/models/automations/actions/strategies/custom_field.rb
@@ -28,7 +28,7 @@
 # See COPYRIGHT and LICENSE files for more details.
 #++
 
-module CustomActions::Actions::Strategies::CustomField
+module Automations::Actions::Strategies::CustomField
   def apply(work_package)
     if work_package.respond_to?(custom_field.attribute_setter)
       set_custom_field_value(work_package)
diff --git a/app/models/custom_actions/actions/strategies/date.rb b/app/models/automations/actions/strategies/date.rb
similarity index 96%
rename from app/models/custom_actions/actions/strategies/date.rb
rename to app/models/automations/actions/strategies/date.rb
index 2ad203fafa83..c69632e86d07 100644
--- a/app/models/custom_actions/actions/strategies/date.rb
+++ b/app/models/automations/actions/strategies/date.rb
@@ -28,7 +28,7 @@
 # See COPYRIGHT and LICENSE files for more details.
 #++
 
-module CustomActions::Actions::Strategies::Date
+module Automations::Actions::Strategies::Date
   def values=(values)
     super(Array(values).map { |v| to_date_or_nil(v) }.uniq)
   end
@@ -48,7 +48,7 @@ def apply(work_package)
 
   def date_to_apply
     if values.first == "%CURRENT_DATE%"
-      Date.today
+      Time.zone.today
     else
       values.first
     end
diff --git a/app/models/custom_actions/actions/strategies/date_property.rb b/app/models/automations/actions/strategies/date_property.rb
similarity index 92%
rename from app/models/custom_actions/actions/strategies/date_property.rb
rename to app/models/automations/actions/strategies/date_property.rb
index e599ca8263da..dfe6c63f6525 100644
--- a/app/models/custom_actions/actions/strategies/date_property.rb
+++ b/app/models/automations/actions/strategies/date_property.rb
@@ -28,6 +28,6 @@
 # See COPYRIGHT and LICENSE files for more details.
 #++
 
-module CustomActions::Actions::Strategies::DateProperty
-  include CustomActions::Actions::Strategies::Date
+module Automations::Actions::Strategies::DateProperty
+  include Automations::Actions::Strategies::Date
 end
diff --git a/app/models/custom_actions/actions/strategies/float.rb b/app/models/automations/actions/strategies/float.rb
similarity index 92%
rename from app/models/custom_actions/actions/strategies/float.rb
rename to app/models/automations/actions/strategies/float.rb
index 69692717366d..103f0101b0b2 100644
--- a/app/models/custom_actions/actions/strategies/float.rb
+++ b/app/models/automations/actions/strategies/float.rb
@@ -28,8 +28,8 @@
 # See COPYRIGHT and LICENSE files for more details.
 #++
 
-module CustomActions::Actions::Strategies::Float
-  include CustomActions::Actions::Strategies::ValidateInRange
+module Automations::Actions::Strategies::Float
+  include Automations::Actions::Strategies::ValidateInRange
 
   def values=(values)
     super(Array(values).map { |v| to_float_or_nil(v) }.uniq)
diff --git a/app/models/custom_actions/actions/strategies/integer.rb b/app/models/automations/actions/strategies/integer.rb
similarity index 89%
rename from app/models/custom_actions/actions/strategies/integer.rb
rename to app/models/automations/actions/strategies/integer.rb
index d69938c4f85c..58942e37a38d 100644
--- a/app/models/custom_actions/actions/strategies/integer.rb
+++ b/app/models/automations/actions/strategies/integer.rb
@@ -28,9 +28,9 @@
 # See COPYRIGHT and LICENSE files for more details.
 #++
 
-module CustomActions::Actions::Strategies::Integer
-  include CustomActions::ValuesToInteger
-  include CustomActions::Actions::Strategies::ValidateInRange
+module Automations::Actions::Strategies::Integer
+  include Automations::ValuesToInteger
+  include Automations::Actions::Strategies::ValidateInRange
 
   def type
     :integer_property
diff --git a/app/models/custom_actions/actions/strategies/link.rb b/app/models/automations/actions/strategies/link.rb
similarity index 93%
rename from app/models/custom_actions/actions/strategies/link.rb
rename to app/models/automations/actions/strategies/link.rb
index 94fc5e11523a..5c822ead478b 100644
--- a/app/models/custom_actions/actions/strategies/link.rb
+++ b/app/models/automations/actions/strategies/link.rb
@@ -28,8 +28,8 @@
 # See COPYRIGHT and LICENSE files for more details.
 #++
 
-module CustomActions::Actions::Strategies::Link
-  include CustomActions::Actions::Strategies::ValuesToString
+module Automations::Actions::Strategies::Link
+  include Automations::Actions::Strategies::ValuesToString
 
   def type
     :link_property
diff --git a/app/models/custom_actions/actions/strategies/me_associated.rb b/app/models/automations/actions/strategies/me_associated.rb
similarity index 92%
rename from app/models/custom_actions/actions/strategies/me_associated.rb
rename to app/models/automations/actions/strategies/me_associated.rb
index 241df7b15bec..9d36a8fb6d5f 100644
--- a/app/models/custom_actions/actions/strategies/me_associated.rb
+++ b/app/models/automations/actions/strategies/me_associated.rb
@@ -28,8 +28,8 @@
 # See COPYRIGHT and LICENSE files for more details.
 #++
 
-module CustomActions::Actions::Strategies::MeAssociated
-  include ::CustomActions::Actions::Strategies::Associated
+module Automations::Actions::Strategies::MeAssociated
+  include ::Automations::Actions::Strategies::Associated
 
   def me_value
     [current_user_value_key, current_user_name]
@@ -66,7 +66,7 @@ def current_user_value_key
   end
 
   def current_user_name
-    I18n.t("custom_actions.actions.assigned_to.executing_user_value")
+    I18n.t("automations.actions.assigned_to.executing_user_value")
   end
 
   def has_me_value?
diff --git a/app/models/custom_actions/actions/strategies/string.rb b/app/models/automations/actions/strategies/string.rb
similarity index 92%
rename from app/models/custom_actions/actions/strategies/string.rb
rename to app/models/automations/actions/strategies/string.rb
index ca8707e5c290..1bf1ff84f926 100644
--- a/app/models/custom_actions/actions/strategies/string.rb
+++ b/app/models/automations/actions/strategies/string.rb
@@ -28,8 +28,8 @@
 # See COPYRIGHT and LICENSE files for more details.
 #++
 
-module CustomActions::Actions::Strategies::String
-  include CustomActions::Actions::Strategies::ValuesToString
+module Automations::Actions::Strategies::String
+  include Automations::Actions::Strategies::ValuesToString
 
   def type
     :string_property
diff --git a/app/models/custom_actions/actions/strategies/text.rb b/app/models/automations/actions/strategies/text.rb
similarity index 92%
rename from app/models/custom_actions/actions/strategies/text.rb
rename to app/models/automations/actions/strategies/text.rb
index 1ceea8308582..d733868aad1a 100644
--- a/app/models/custom_actions/actions/strategies/text.rb
+++ b/app/models/automations/actions/strategies/text.rb
@@ -28,8 +28,8 @@
 # See COPYRIGHT and LICENSE files for more details.
 #++
 
-module CustomActions::Actions::Strategies::Text
-  include CustomActions::Actions::Strategies::ValuesToString
+module Automations::Actions::Strategies::Text
+  include Automations::Actions::Strategies::ValuesToString
 
   def type
     :text_property
diff --git a/app/models/custom_actions/actions/strategies/user_custom_field.rb b/app/models/automations/actions/strategies/user_custom_field.rb
similarity index 93%
rename from app/models/custom_actions/actions/strategies/user_custom_field.rb
rename to app/models/automations/actions/strategies/user_custom_field.rb
index 022c723cf855..8609e9e117e0 100644
--- a/app/models/custom_actions/actions/strategies/user_custom_field.rb
+++ b/app/models/automations/actions/strategies/user_custom_field.rb
@@ -28,9 +28,9 @@
 # See COPYRIGHT and LICENSE files for more details.
 #++
 
-module CustomActions::Actions::Strategies::UserCustomField
-  include ::CustomActions::Actions::Strategies::CustomField
-  include ::CustomActions::Actions::Strategies::MeAssociated
+module Automations::Actions::Strategies::UserCustomField
+  include ::Automations::Actions::Strategies::CustomField
+  include ::Automations::Actions::Strategies::MeAssociated
 
   def type
     :user
diff --git a/app/models/custom_actions/actions/strategies/validate_in_range.rb b/app/models/automations/actions/strategies/validate_in_range.rb
similarity index 97%
rename from app/models/custom_actions/actions/strategies/validate_in_range.rb
rename to app/models/automations/actions/strategies/validate_in_range.rb
index 51b83d111207..b90e13800b6a 100644
--- a/app/models/custom_actions/actions/strategies/validate_in_range.rb
+++ b/app/models/automations/actions/strategies/validate_in_range.rb
@@ -28,7 +28,7 @@
 # See COPYRIGHT and LICENSE files for more details.
 #++
 
-module CustomActions::Actions::Strategies::ValidateInRange
+module Automations::Actions::Strategies::ValidateInRange
   def minimum
     nil
   end
diff --git a/app/models/custom_actions/actions/strategies/values_to_string.rb b/app/models/automations/actions/strategies/values_to_string.rb
similarity index 96%
rename from app/models/custom_actions/actions/strategies/values_to_string.rb
rename to app/models/automations/actions/strategies/values_to_string.rb
index 94e26c46905e..d2e90002ad85 100644
--- a/app/models/custom_actions/actions/strategies/values_to_string.rb
+++ b/app/models/automations/actions/strategies/values_to_string.rb
@@ -28,7 +28,7 @@
 # See COPYRIGHT and LICENSE files for more details.
 #++
 
-module CustomActions::Actions::Strategies::ValuesToString
+module Automations::Actions::Strategies::ValuesToString
   def values=(values)
     super(Array(values).map { |v| to_string_or_nil(v) }.uniq)
   end
diff --git a/app/models/custom_actions/actions/type.rb b/app/models/automations/actions/type.rb
similarity index 92%
rename from app/models/custom_actions/actions/type.rb
rename to app/models/automations/actions/type.rb
index 8d156c2ee856..0fa83ce52252 100644
--- a/app/models/custom_actions/actions/type.rb
+++ b/app/models/automations/actions/type.rb
@@ -28,8 +28,8 @@
 # See COPYRIGHT and LICENSE files for more details.
 #++
 
-class CustomActions::Actions::Type < CustomActions::Actions::Base
-  include CustomActions::Actions::Strategies::Associated
+class Automations::Actions::Type < Automations::Actions::Base
+  include Automations::Actions::Strategies::Associated
 
   PRIORITY = 20
 
diff --git a/app/models/custom_actions/conditions/base.rb b/app/models/automations/conditions/base.rb
similarity index 76%
rename from app/models/custom_actions/conditions/base.rb
rename to app/models/automations/conditions/base.rb
index 9852d382fbc3..c4875674c265 100644
--- a/app/models/custom_actions/conditions/base.rb
+++ b/app/models/automations/conditions/base.rb
@@ -28,11 +28,11 @@
 # See COPYRIGHT and LICENSE files for more details.
 #++
 
-class CustomActions::Conditions::Base
+class Automations::Conditions::Base
   attr_reader :values
 
-  prepend CustomActions::ValuesToInteger
-  include CustomActions::ValidateAllowedValue
+  prepend Automations::ValuesToInteger
+  include Automations::ValidateAllowedValue
 
   def initialize(values = nil)
     self.values = values
@@ -62,9 +62,7 @@ def fulfilled_by?(work_package, _user)
     (work_package.respond_to?(:"#{key}_id") && values.include?(work_package.send(:"#{key}_id")))
   end
 
-  def key
-    self.class.key
-  end
+  delegate :key, to: :class
 
   def self.key
     raise SubclassResponsibilityError
@@ -74,38 +72,38 @@ def validate(errors)
     validate_allowed_value(errors, :conditions)
   end
 
-  def self.getter(custom_action)
-    ids = custom_action.send(association_ids)
+  def self.getter(automation)
+    ids = automation.send(association_ids)
 
     new(ids) if ids.any?
   end
 
-  def self.setter(custom_action, condition)
+  def self.setter(automation, condition)
     if condition
-      custom_action.send(:"#{association_ids}=", condition.values)
+      automation.send(:"#{association_ids}=", condition.values)
     else
-      custom_action.send(:"#{association_key}").clear
+      automation.send(:"#{association_key}").clear
     end
   end
 
-  def self.custom_action_scope(work_packages, user)
-    custom_action_scope_has_current(work_packages, user)
-      .or(custom_action_scope_has_no)
+  def self.automation_scope(work_packages, user)
+    automation_scope_has_current(work_packages, user)
+      .or(automation_scope_has_no)
   end
 
-  def self.custom_action_scope_has_current(work_packages, _user)
-    CustomAction
+  def self.automation_scope_has_current(work_packages, _user)
+    Automation
       .includes(association_key)
       .where(habtm_table => { key_id => Array(work_packages).map { |w| w.send(key_id) }.uniq })
   end
-  private_class_method :custom_action_scope_has_current
+  private_class_method :automation_scope_has_current
 
-  def self.custom_action_scope_has_no
-    CustomAction
+  def self.automation_scope_has_no
+    Automation
       .includes(association_key)
       .where(habtm_table => { key_id => nil })
   end
-  private_class_method :custom_action_scope_has_no
+  private_class_method :automation_scope_has_no
 
   def self.pluralized_key
     key.to_s.pluralize.to_sym
@@ -113,7 +111,7 @@ def self.pluralized_key
   private_class_method :pluralized_key
 
   def self.habtm_table
-    :"custom_actions_#{pluralized_key}"
+    :"automations_#{pluralized_key}"
   end
   private_class_method :habtm_table
 
diff --git a/app/models/custom_actions/conditions/inexistent.rb b/app/models/automations/conditions/inexistent.rb
similarity index 94%
rename from app/models/custom_actions/conditions/inexistent.rb
rename to app/models/automations/conditions/inexistent.rb
index 5cbf25aac5fe..04702b51e0d9 100644
--- a/app/models/custom_actions/conditions/inexistent.rb
+++ b/app/models/automations/conditions/inexistent.rb
@@ -28,7 +28,7 @@
 # See COPYRIGHT and LICENSE files for more details.
 #++
 
-class CustomActions::Conditions::Inexistent < CustomActions::Conditions::Base
+class Automations::Conditions::Inexistent < Automations::Conditions::Base
   def self.key
     :inexistent
   end
diff --git a/app/models/custom_actions/conditions/project.rb b/app/models/automations/conditions/project.rb
similarity index 95%
rename from app/models/custom_actions/conditions/project.rb
rename to app/models/automations/conditions/project.rb
index 807a7bdfc79a..296532dfc3b8 100644
--- a/app/models/custom_actions/conditions/project.rb
+++ b/app/models/automations/conditions/project.rb
@@ -28,7 +28,7 @@
 # See COPYRIGHT and LICENSE files for more details.
 #++
 
-class CustomActions::Conditions::Project < CustomActions::Conditions::Base
+class Automations::Conditions::Project < Automations::Conditions::Base
   def self.key
     :project
   end
diff --git a/app/models/custom_actions/conditions/role.rb b/app/models/automations/conditions/role.rb
similarity index 86%
rename from app/models/custom_actions/conditions/role.rb
rename to app/models/automations/conditions/role.rb
index 77af34115ff9..29d2fa37637d 100644
--- a/app/models/custom_actions/conditions/role.rb
+++ b/app/models/automations/conditions/role.rb
@@ -28,10 +28,10 @@
 # See COPYRIGHT and LICENSE files for more details.
 #++
 
-class CustomActions::Conditions::Role < CustomActions::Conditions::Base
+class Automations::Conditions::Role < Automations::Conditions::Base
   def fulfilled_by?(work_package, user)
     values.empty? ||
-      (self.class.roles_in_project(work_package, user).map(&:id) & values).any?
+      self.class.roles_in_project(work_package, user).map(&:id).intersect?(values)
   end
 
   class << self
@@ -49,8 +49,8 @@ def roles_in_project(work_packages, user)
 
     private
 
-    def custom_action_scope_has_current(work_packages, user)
-      CustomAction
+    def automation_scope_has_current(work_packages, user)
+      Automation
         .includes(association_key)
         .where(habtm_table => { key_id => roles_in_project(work_packages, user) })
     end
@@ -67,11 +67,11 @@ def projects_of(work_packages)
     end
 
     def with_request_store(projects)
-      RequestStore.store[:custom_actions_role] ||= Hash.new do |hash, hash_projects|
+      RequestStore.store[:automations_role] ||= Hash.new do |hash, hash_projects|
         hash[hash_projects] = yield hash_projects
       end
 
-      RequestStore.store[:custom_actions_role][projects]
+      RequestStore.store[:automations_role][projects]
     end
   end
 
diff --git a/app/models/custom_actions/conditions/status.rb b/app/models/automations/conditions/status.rb
similarity index 94%
rename from app/models/custom_actions/conditions/status.rb
rename to app/models/automations/conditions/status.rb
index c6b246e0d65a..c5069e596d83 100644
--- a/app/models/custom_actions/conditions/status.rb
+++ b/app/models/automations/conditions/status.rb
@@ -28,7 +28,7 @@
 # See COPYRIGHT and LICENSE files for more details.
 #++
 
-class CustomActions::Conditions::Status < CustomActions::Conditions::Base
+class Automations::Conditions::Status < Automations::Conditions::Base
   def self.key
     :status
   end
diff --git a/app/models/custom_actions/conditions/type.rb b/app/models/automations/conditions/type.rb
similarity index 95%
rename from app/models/custom_actions/conditions/type.rb
rename to app/models/automations/conditions/type.rb
index af6ff9ba148f..ba60a021e22e 100644
--- a/app/models/custom_actions/conditions/type.rb
+++ b/app/models/automations/conditions/type.rb
@@ -28,7 +28,7 @@
 # See COPYRIGHT and LICENSE files for more details.
 #++
 
-class CustomActions::Conditions::Type < CustomActions::Conditions::Base
+class Automations::Conditions::Type < Automations::Conditions::Base
   def self.key
     :type
   end
diff --git a/app/models/custom_actions/register.rb b/app/models/automations/register.rb
similarity index 64%
rename from app/models/custom_actions/register.rb
rename to app/models/automations/register.rb
index e49123fd52cb..0645fa7dc24e 100644
--- a/app/models/custom_actions/register.rb
+++ b/app/models/automations/register.rb
@@ -28,32 +28,32 @@
 # See COPYRIGHT and LICENSE files for more details.
 #++
 
-module CustomActions::Register
+module Automations::Register
   class << self
     def actions
       [
-        CustomActions::Actions::AssignedTo,
-        CustomActions::Actions::Responsible,
-        CustomActions::Actions::Status,
-        CustomActions::Actions::Priority,
-        CustomActions::Actions::CustomField,
-        CustomActions::Actions::Type,
-        CustomActions::Actions::Project,
-        CustomActions::Actions::Notify,
-        CustomActions::Actions::DoneRatio,
-        CustomActions::Actions::EstimatedHours,
-        CustomActions::Actions::StartDate,
-        CustomActions::Actions::DueDate,
-        CustomActions::Actions::Date
+        Automations::Actions::AssignedTo,
+        Automations::Actions::Responsible,
+        Automations::Actions::Status,
+        Automations::Actions::Priority,
+        Automations::Actions::CustomField,
+        Automations::Actions::Type,
+        Automations::Actions::Project,
+        Automations::Actions::Notify,
+        Automations::Actions::DoneRatio,
+        Automations::Actions::EstimatedHours,
+        Automations::Actions::StartDate,
+        Automations::Actions::DueDate,
+        Automations::Actions::Date
       ]
     end
 
     def conditions
       [
-        CustomActions::Conditions::Status,
-        CustomActions::Conditions::Role,
-        CustomActions::Conditions::Type,
-        CustomActions::Conditions::Project
+        Automations::Conditions::Status,
+        Automations::Conditions::Role,
+        Automations::Conditions::Type,
+        Automations::Conditions::Project
       ]
     end
   end
diff --git a/app/models/automations/triggers/base.rb b/app/models/automations/triggers/base.rb
new file mode 100644
index 000000000000..cc9d2958d6e4
--- /dev/null
+++ b/app/models/automations/triggers/base.rb
@@ -0,0 +1,41 @@
+# frozen_string_literal: true
+
+#-- copyright
+# OpenProject is an open source project management software.
+# Copyright (C) the OpenProject GmbH
+#
+# This program is free software; you can redistribute it and/or
+# modify it under the terms of the GNU General Public License version 3.
+#
+# OpenProject is a fork of ChiliProject, which is a fork of Redmine. The copyright follows:
+# Copyright (C) 2006-2013 Jean-Philippe Lang
+# Copyright (C) 2010-2013 the ChiliProject Team
+#
+# This program is free software; you can redistribute it and/or
+# modify it under the terms of the GNU General Public License
+# as published by the Free Software Foundation; either version 2
+# of the License, or (at your option) any later version.
+#
+# This program is distributed in the hope that it will be useful,
+# but WITHOUT ANY WARRANTY; without even the implied warranty of
+# MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the
+# GNU General Public License for more details.
+#
+# You should have received a copy of the GNU General Public License
+# along with this program; if not, write to the Free Software
+# Foundation, Inc., 51 Franklin Street, Fifth Floor, Boston, MA  02110-1301, USA.
+#
+# See COPYRIGHT and LICENSE files for more details.
+#++
+
+module Automations
+  module Triggers
+    class Base < ApplicationRecord
+      self.table_name = "automation_triggers"
+
+      belongs_to :automation, inverse_of: :triggers
+
+      acts_as_list scope: :automation
+    end
+  end
+end
diff --git a/spec/factories/custom_action_factory.rb b/app/models/automations/triggers/manual.rb
similarity index 86%
rename from spec/factories/custom_action_factory.rb
rename to app/models/automations/triggers/manual.rb
index 1fa4b6cc3f35..3b80a7016f8b 100644
--- a/spec/factories/custom_action_factory.rb
+++ b/app/models/automations/triggers/manual.rb
@@ -28,9 +28,12 @@
 # See COPYRIGHT and LICENSE files for more details.
 #++
 
-FactoryBot.define do
-  factory :custom_action do
-    sequence(:name) { |n| "Custom action #{n} - name" }
-    sequence(:description) { |n| "Custom action #{n} - description" }
+module Automations
+  module Triggers
+    class Manual < Base
+      store_attribute :options, :button_label, :string
+
+      validates :button_label, presence: true, length: { maximum: 255 }
+    end
   end
 end
diff --git a/app/models/custom_actions/validate_allowed_value.rb b/app/models/automations/validate_allowed_value.rb
similarity index 50%
rename from app/models/custom_actions/validate_allowed_value.rb
rename to app/models/automations/validate_allowed_value.rb
index b85f7678b066..32dd280e20d0 100644
--- a/app/models/custom_actions/validate_allowed_value.rb
+++ b/app/models/automations/validate_allowed_value.rb
@@ -1,5 +1,33 @@
 # frozen_string_literal: true
 
+#-- copyright
+# OpenProject is an open source project management software.
+# Copyright (C) the OpenProject GmbH
+#
+# This program is free software; you can redistribute it and/or
+# modify it under the terms of the GNU General Public License version 3.
+#
+# OpenProject is a fork of ChiliProject, which is a fork of Redmine. The copyright follows:
+# Copyright (C) 2006-2013 Jean-Philippe Lang
+# Copyright (C) 2010-2013 the ChiliProject Team
+#
+# This program is free software; you can redistribute it and/or
+# modify it under the terms of the GNU General Public License
+# as published by the Free Software Foundation; either version 2
+# of the License, or (at your option) any later version.
+#
+# This program is distributed in the hope that it will be useful,
+# but WITHOUT ANY WARRANTY; without even the implied warranty of
+# MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the
+# GNU General Public License for more details.
+#
+# You should have received a copy of the GNU General Public License
+# along with this program; if not, write to the Free Software
+# Foundation, Inc., 51 Franklin Street, Fifth Floor, Boston, MA  02110-1301, USA.
+#
+# See COPYRIGHT and LICENSE files for more details.
+#++
+
 # OpenProject is a fork of ChiliProject, which is a fork of Redmine. The copyright follows:
 # Copyright (C) 2006-2017 Jean-Philippe Lang
 # Copyright (C) 2010-2013 the ChiliProject Team
@@ -21,7 +49,7 @@
 # See COPYRIGHT and LICENSE files for more details.
 #++
 
-module CustomActions::ValidateAllowedValue
+module Automations::ValidateAllowedValue
   private
 
   def validate_allowed_value(errors, attribute)
diff --git a/app/models/custom_actions/values_to_integer.rb b/app/models/automations/values_to_integer.rb
similarity index 97%
rename from app/models/custom_actions/values_to_integer.rb
rename to app/models/automations/values_to_integer.rb
index c36aa8fbea69..6894a3f90c70 100644
--- a/app/models/custom_actions/values_to_integer.rb
+++ b/app/models/automations/values_to_integer.rb
@@ -28,7 +28,7 @@
 # See COPYRIGHT and LICENSE files for more details.
 #++
 
-module CustomActions::ValuesToInteger
+module Automations::ValuesToInteger
   def values=(values)
     super(Array(values).map { |v| to_integer_or_nil(v) }.uniq)
   end
diff --git a/app/models/permitted_params.rb b/app/models/permitted_params.rb
index ec0b77f51ecf..8ac8956447cc 100644
--- a/app/models/permitted_params.rb
+++ b/app/models/permitted_params.rb
@@ -92,12 +92,12 @@ def custom_field
     params.require(:custom_field).permit(*self.class.permitted_attributes[:custom_field])
   end
 
-  def custom_action
+  def automation
     whitelisted = params
-      .require(:custom_action)
-      .permit(*self.class.permitted_attributes[:custom_action])
+      .require(:automation)
+      .permit(*self.class.permitted_attributes[:automation])
 
-    whitelisted.merge(params[:custom_action].slice(:actions, :conditions).permit!)
+    whitelisted.merge(params[:automation].slice(:actions, :conditions).permit!)
   end
 
   def custom_field_type
@@ -507,11 +507,12 @@ def self.permitted_attributes
           hexcode
           move_to
         ),
-        custom_action: %i(
-          name
-          description
-          move_to
-        ),
+        automation: [
+          :name,
+          :description,
+          :move_to,
+          { triggers_attributes: [:id, :type, :position, { options: {} }, :_destroy] }
+        ],
         custom_field: [
           :editable,
           :field_format,
diff --git a/app/models/work_package.rb b/app/models/work_package.rb
index 0706f73d421e..d4066af82f45 100644
--- a/app/models/work_package.rb
+++ b/app/models/work_package.rb
@@ -36,7 +36,7 @@ class WorkPackage < ApplicationRecord
   include WorkPackage::AskBeforeDestruction
   include WorkPackage::TimeEntriesCleaner
   include WorkPackage::Ancestors
-  include WorkPackage::CustomActioned
+  include WorkPackage::Automatable
   include WorkPackage::Hooks
   # Must stay above WorkPackage::Journalized: its after_save persists the
   # version rows that the journal snapshot then reads.
diff --git a/app/models/work_package/custom_actioned.rb b/app/models/work_package/automatable.rb
similarity index 79%
rename from app/models/work_package/custom_actioned.rb
rename to app/models/work_package/automatable.rb
index 0d88d078c315..cf63ed4a3b76 100644
--- a/app/models/work_package/custom_actioned.rb
+++ b/app/models/work_package/automatable.rb
@@ -28,16 +28,21 @@
 # See COPYRIGHT and LICENSE files for more details.
 #++
 
-module WorkPackage::CustomActioned
+module WorkPackage::Automatable
   extend ActiveSupport::Concern
 
   included do
-    def custom_actions(user)
-      @custom_actions = CustomAction
-                        .available_conditions
-                        .inject(CustomAction.all) do |scope, condition|
-        scope.merge(condition.custom_action_scope(self, user))
+    def automations(user)
+      @automations = Automation
+                     .available_conditions
+                     .inject(Automation.all) do |scope, condition|
+        scope.merge(condition.automation_scope(self, user))
       end
     end
+
+    # API compatibility for /api/v3/custom_actions
+    def custom_actions(user)
+      automations(user)
+    end
   end
 end
diff --git a/app/models/work_package_custom_field.rb b/app/models/work_package_custom_field.rb
index 45547925f280..792076725138 100644
--- a/app/models/work_package_custom_field.rb
+++ b/app/models/work_package_custom_field.rb
@@ -44,7 +44,7 @@ class WorkPackageCustomField < CustomField
   scopes :visible,
          :on_visible_type_and_project
 
-  scope :usable_as_custom_action, -> {
+  scope :usable_as_automation, -> {
     where.not(field_format: %w[hierarchy weighted_item_list])
          .order(:name)
   }
diff --git a/app/services/custom_actions/base_service.rb b/app/services/automations/base_service.rb
similarity index 75%
rename from app/services/custom_actions/base_service.rb
rename to app/services/automations/base_service.rb
index dfc18ab4f7ee..02449a8dbd33 100644
--- a/app/services/custom_actions/base_service.rb
+++ b/app/services/automations/base_service.rb
@@ -28,7 +28,7 @@
 # See COPYRIGHT and LICENSE files for more details.
 #++
 
-class CustomActions::BaseService
+class Automations::BaseService
   include Shared::BlockService
 
   attr_accessor :user
@@ -38,7 +38,7 @@ def call(attributes:,
            &)
     set_attributes(action, attributes)
 
-    contract = CustomActions::CuContract.new(action)
+    contract = Automations::CuContract.new(action, user)
     result = ServiceResult.new(success: contract.validate && action.save,
                                result: action,
                                errors: contract.errors)
@@ -51,10 +51,12 @@ def call(attributes:,
   def set_attributes(action, attributes)
     actions_attributes = attributes.delete(:actions)
     conditions_attributes = attributes.delete(:conditions)
-    action.attributes = attributes
+    triggers_attributes = attributes.delete(:triggers_attributes)
 
+    action.attributes = attributes
     set_actions(action, actions_attributes.symbolize_keys) if actions_attributes
     set_conditions(action, conditions_attributes.symbolize_keys) if conditions_attributes
+    set_triggers(action, triggers_attributes)
   end
 
   def set_actions(action, actions_attributes)
@@ -66,21 +68,15 @@ def set_actions(action, actions_attributes)
   end
 
   def remove_actions(action, keys)
-    keys.each do |key|
-      remove_action(action, key)
-    end
+    keys.each { |key| remove_action(action, key) }
   end
 
   def update_actions(action, key_values)
-    key_values.each do |key, values|
-      update_action(action, key, values)
-    end
+    key_values.each { |key, values| update_action(action, key, values) }
   end
 
   def add_actions(action, key_values)
-    key_values.each do |key, values|
-      add_action(action, key, values)
-    end
+    key_values.each { |key, values| add_action(action, key, values) }
   end
 
   def update_action(action, key, values)
@@ -102,10 +98,23 @@ def set_conditions(action, conditions_attributes)
   end
 
   def available_action_for(action, key)
-    action.available_actions.detect { |a| a.key == key } || CustomActions::Actions::Inexistent
+    action.available_actions.detect { |a| a.key == key } || Automations::Actions::Inexistent
   end
 
   def available_condition_for(action, key)
-    action.available_conditions.detect { |a| a.key == key } || CustomActions::Conditions::Inexistent
+    action.available_conditions.detect { |a| a.key == key } || Automations::Conditions::Inexistent
+  end
+
+  def set_triggers(action, attributes)
+    attributes ||= default_trigger_attributes(action)
+    return if attributes.blank?
+
+    action.assign_attributes(triggers_attributes: attributes)
+  end
+
+  def default_trigger_attributes(action)
+    return [] if action.triggers.any?(Automations::Triggers::Manual)
+
+    [{ type: "Automations::Triggers::Manual", options: { button_label: action.name } }]
   end
 end
diff --git a/app/services/custom_actions/create_service.rb b/app/services/automations/create_service.rb
similarity index 90%
rename from app/services/custom_actions/create_service.rb
rename to app/services/automations/create_service.rb
index 1feb0a003972..32def61a4c06 100644
--- a/app/services/custom_actions/create_service.rb
+++ b/app/services/automations/create_service.rb
@@ -28,14 +28,13 @@
 # See COPYRIGHT and LICENSE files for more details.
 #++
 
-class CustomActions::CreateService < CustomActions::BaseService
+class Automations::CreateService < Automations::BaseService
   def initialize(user:)
     self.user = user
+    super()
   end
 
-  def call(attributes:,
-           action: CustomAction.new,
-           &block)
+  def call(attributes:, action: Automation.new, &block)
     super
   end
 end
diff --git a/app/services/custom_actions/update_service.rb b/app/services/automations/update_service.rb
similarity index 95%
rename from app/services/custom_actions/update_service.rb
rename to app/services/automations/update_service.rb
index 12d1d04add66..193b6c10e782 100644
--- a/app/services/custom_actions/update_service.rb
+++ b/app/services/automations/update_service.rb
@@ -28,13 +28,14 @@
 # See COPYRIGHT and LICENSE files for more details.
 #++
 
-class CustomActions::UpdateService < CustomActions::BaseService
+class Automations::UpdateService < Automations::BaseService
   attr_accessor :user,
                 :action
 
   def initialize(action:, user:)
     self.action = action
     self.user = user
+    super()
   end
 
   def call(attributes:, &)
diff --git a/app/services/custom_actions/update_work_package_service.rb b/app/services/automations/update_work_package_service.rb
similarity index 91%
rename from app/services/custom_actions/update_work_package_service.rb
rename to app/services/automations/update_work_package_service.rb
index d4058deaf335..03e5d6e8f004 100644
--- a/app/services/custom_actions/update_work_package_service.rb
+++ b/app/services/automations/update_work_package_service.rb
@@ -28,7 +28,7 @@
 # See COPYRIGHT and LICENSE files for more details.
 #++
 
-class CustomActions::UpdateWorkPackageService
+class Automations::UpdateWorkPackageService
   include Shared::BlockService
   include Contracted
 
@@ -56,13 +56,10 @@ def call(work_package:, &)
 
   def apply_actions(work_package, actions)
     changes_before = work_package.changes.dup
-
     apply_actions_sorted(work_package, actions)
 
     success, errors = validate(work_package, user)
-    unless success
-      retry_apply_actions(work_package, actions, errors, changes_before)
-    end
+    retry_apply_actions(work_package, actions, errors, changes_before) unless success
   end
 
   def retry_apply_actions(work_package, actions, errors, changes_before)
@@ -76,14 +73,11 @@ def retry_apply_actions(work_package, actions, errors, changes_before)
 
   def without_invalid_actions(actions, errors)
     invalid_keys = errors.attribute_names.map { |k| append_id(k) }
-
     actions.reject { |a| invalid_keys.include?(append_id(a.key)) }
   end
 
   def apply_actions_sorted(work_package, actions)
-    actions
-      .sort_by(&:priority)
-      .each { |a| a.apply(work_package) }
+    actions.sort_by(&:priority).each { |a| a.apply(work_package) }
   end
 
   def append_id(sym)
diff --git a/app/views/custom_actions/_form.html.erb b/app/views/automations/_form.html.erb
similarity index 60%
rename from app/views/custom_actions/_form.html.erb
rename to app/views/automations/_form.html.erb
index 90bfaa92e1f1..857ab1133c84 100644
--- a/app/views/custom_actions/_form.html.erb
+++ b/app/views/automations/_form.html.erb
@@ -1,4 +1,34 @@
-<% active_section_keys = @custom_action.actions.map(&:key) %>
+<%#-- copyright
+OpenProject is an open source project management software.
+Copyright (C) the OpenProject GmbH
+
+This program is free software; you can redistribute it and/or
+modify it under the terms of the GNU General Public License version 3.
+
+OpenProject is a fork of ChiliProject, which is a fork of Redmine. The copyright follows:
+Copyright (C) 2006-2013 Jean-Philippe Lang
+Copyright (C) 2010-2013 the ChiliProject Team
+
+This program is free software; you can redistribute it and/or
+modify it under the terms of the GNU General Public License
+as published by the Free Software Foundation; either version 2
+of the License, or (at your option) any later version.
+
+This program is distributed in the hope that it will be useful,
+but WITHOUT ANY WARRANTY; without even the implied warranty of
+MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the
+GNU General Public License for more details.
+
+You should have received a copy of the GNU General Public License
+along with this program; if not, write to the Free Software
+Foundation, Inc., 51 Franklin Street, Fifth Floor, Boston, MA  02110-1301, USA.
+
+See COPYRIGHT and LICENSE files for more details.
+
+++#%>
+
+<% active_section_keys = @automation.actions.map(&:key) %>
+<% trigger = @automation.triggers.detect { |t| t.is_a?(Automations::Triggers::Manual) } || @automation.triggers.build(type: "Automations::Triggers::Manual") %>
 
 <div class="form--field -required">
   <%= f.text_field :name, required: true, container_class: "-middle" %>
@@ -7,16 +37,27 @@
   <%= f.text_area :description, container_class: "-middle" %>
 </div>
 
-<fieldset class="form--fieldset" id="custom-actions-form--conditions">
-  <legend class="form--fieldset-legend">
-    <%= t("custom_actions.conditions") %>
-  </legend>
+<fieldset class="form--fieldset" id="automations-form--trigger">
+  <legend class="form--fieldset-legend"><%= t("automations.trigger") %></legend>
+  <div class="form--field">
+    <%= styled_label_tag "automation_trigger_type", t("automations.triggers.name"), class: "-top" %>
+    <div class="form--field-container">
+      <%= styled_text_field_tag "automation_trigger_type",
+                                t("automations.triggers.manual.label"),
+                                disabled: true,
+                                container_class: "-middle" %>
+    </div>
+  </div>
+  <%= render partial: "trigger_fields_manual", locals: { trigger: } %>
+</fieldset>
 
-  <% @custom_action.all_conditions.each do |condition| %>
-    <div class="form--field">
-      <%= styled_label_tag("custom_action_conditions_#{condition.key}", condition.human_name, class: "-top") %>
-      <% input_name = "custom_action[conditions][#{condition.key}]" %>
+<fieldset class="form--fieldset" id="automations-form--conditions">
+  <legend class="form--fieldset-legend"><%= t("automations.conditions") %></legend>
 
+  <% @automation.all_conditions.each do |condition| %>
+    <div class="form--field">
+      <%= styled_label_tag("automation_conditions_#{condition.key}", condition.human_name, class: "-top") %>
+      <% input_name = "automation[conditions][#{condition.key}]" %>
       <div class="form--field-container">
         <div class="form--select-container -middle">
           <% if condition.key == :project %>
@@ -26,7 +67,7 @@
                                         filters: [{ name: "active", operator: "=", values: ["t"] }],
                                         resource: "projects",
                                         inputName: input_name,
-                                        labelForId: "custom_action_actions_#{condition.key}",
+                                        labelForId: "automation_conditions_#{condition.key}",
                                         inputValue: condition.values
                                       } %>
           <% else %>
@@ -38,31 +79,28 @@
                                         model: condition.value_objects.map { |v| { id: v[:value], name: v[:label] } },
                                         inputName: input_name,
                                         bindLabel: "name",
-                                        labelForId: "custom_action_conditions_#{condition.key}"
+                                        labelForId: "automation_conditions_#{condition.key}"
                                       } %>
           <% end %>
         </div>
       </div>
     </div>
-    <div class="form--space"></div>
   <% end %>
 </fieldset>
 
-<fieldset class="form--fieldset" id="custom-actions-form--actions">
-  <legend class="form--fieldset-legend">
-    <%= t("custom_actions.actions.name") %>
-  </legend>
+<fieldset class="form--fieldset" id="automations-form--actions">
+  <legend class="form--fieldset-legend"><%= t("automations.actions.name") %></legend>
 
-  <div id="custom-actions-form--active-actions">
-    <% @custom_action.all_actions.each do |action| %>
+  <div id="automations-form--active-actions">
+    <% @automation.all_actions.each do |action| %>
       <section class="hide-section"
                data-hide-sections-target="section"
                data-name="<%= action.key %>"
                <%= tag.attributes(data: { section_name: action.key }, hidden: active_section_keys.exclude?(action.key)) %>>
         <div class="form--field">
-          <%= styled_label_tag("custom_action_actions_#{action.key}", action.human_name, class: "-top") %>
+          <%= styled_label_tag("automation_actions_#{action.key}", action.human_name, class: "-top") %>
+          <% input_name = "automation[actions][#{action.key}]" %>
 
-          <% input_name = "custom_action[actions][#{action.key}]" %>
           <% if %i(associated_property boolean user project).include?(action.type) %>
             <div class="form--field-container">
               <div class="form--select-container -middle">
@@ -75,7 +113,7 @@
                                               resource: "projects",
                                               inputName: input_name,
                                               appendTo: "body",
-                                              labelForId: "custom_action_actions_#{action.key}",
+                                              labelForId: "automation_actions_#{action.key}",
                                               inputValue: action.values.first
                                             } %>
                 <% in { type: :user, custom_field_based: false } %>
@@ -98,7 +136,7 @@
                                                 { id: action.current_user_value_key, name: action.current_user_name }
                                               ],
                                               searchKey: "any_name_attribute",
-                                              labelForId: "custom_action_actions_#{action.key}",
+                                              labelForId: "automation_actions_#{action.key}",
                                               focusDirectly: false
                                             } %>
                 <% else %>
@@ -112,12 +150,12 @@
                                               model: action.multi_value? ? selected : selected.first,
                                               inputName: input_name,
                                               bindLabel: "name",
-                                              labelForId: "custom_action_actions_#{action.key}"
+                                              labelForId: "automation_actions_#{action.key}"
                                             } %>
                 <% end %>
               </div>
             </div>
-          <% elsif %i(date_property).include?(action.type) %>
+          <% elsif action.type == :date_property %>
             <div class="form--field-container">
               <% date = action.values.first %>
               <%= angular_component_tag "opce-custom-date-action-admin",
@@ -125,74 +163,41 @@
             </div>
           <% elsif %i(string_property text_property).include?(action.type) %>
             <div class="form--field-container">
-              <%= styled_text_field_tag input_name,
-                                        action.values,
-                                        container_class: "-slim",
-                                        step: "any" %>
+              <%= styled_text_field_tag input_name, action.values, container_class: "-slim" %>
             </div>
-          <% elsif %i(link_property).include?(action.type) %>
+          <% elsif action.type == :link_property %>
             <div class="form--field-container">
-              <%= styled_url_field_tag input_name,
-                                       action.values,
-                                       container_class: "-slim",
-                                       step: "any" %>
+              <%= styled_url_field_tag input_name, action.values, container_class: "-slim" %>
             </div>
-          <% elsif action.type == :float_property %>
+          <% elsif %i(float_property integer_property).include?(action.type) %>
             <div class="form--field-container">
               <%= styled_number_field_tag input_name,
                                           action.values,
                                           container_class: "-slim",
                                           min: action.minimum,
                                           max: action.maximum,
-                                          step: "any" %>
-            </div>
-          <% elsif action.type == :integer_property %>
-            <div class="form--field-container">
-              <%= styled_number_field_tag input_name,
-                                          action.values,
-                                          container_class: "-slim",
-                                          min: action.minimum,
-                                          max: action.maximum,
-                                          step: 1 %>
+                                          step: action.type == :integer_property ? 1 : "any" %>
             </div>
           <% end %>
-          <%=
-            render(
-              Primer::Beta::IconButton.new(
-                icon: :x,
-                size: :small,
-                scheme: :invisible,
-                type: :button,
-                aria: { label: t(:button_close) },
-                data: { action: "click->hide-sections#hide" }
-              )
-            )
-          %>
+
+          <%= render(Primer::Beta::IconButton.new(icon: :x, size: :small, scheme: :invisible, type: :button, aria: { label: t(:button_close) }, data: { action: "click->hide-sections#hide" })) %>
         </div>
       </section>
     <% end %>
   </div>
 
-  <div class="form--space"></div>
-
   <div class="form--field">
-    <label class="form--label" for="add-custom-action-select">
+    <label class="form--label" for="add-automation-action-select">
       <%= render(Primer::Beta::Octicon.new(icon: :plus, size: :small)) %>
-      <%= I18n.t(:"custom_actions.actions.add") %>
+      <%= I18n.t(:"automations.actions.add") %>
     </label>
     <span class="form--field-container">
       <span class="form--select-container -middle">
         <%= select_tag "add_action",
-                       options_for_select(
-                         @custom_action.all_actions.map { |a| [a.human_name, a.key] },
-                         disabled: active_section_keys
-                       ),
-                       id: "add-custom-action-select",
-                       prompt: t(:"custom_actions.actions.add"),
-                       data: {
-                         "hide-sections-target": "select",
-                         action: "change->hide-sections#add"
-                       },
+                       options_for_select(@automation.all_actions.map { |a| [a.human_name, a.key] }, disabled: active_section_keys),
+                       id: "add-automation-action-select",
+                       prompt: t(:"automations.actions.add"),
+                       data: { "hide-sections-target": "select", action: "change->hide-sections#add" },
                        class: "form--select" %>
       </span>
     </span>
diff --git a/app/views/automations/_trigger_fields_manual.html.erb b/app/views/automations/_trigger_fields_manual.html.erb
new file mode 100644
index 000000000000..35e4a2dd8346
--- /dev/null
+++ b/app/views/automations/_trigger_fields_manual.html.erb
@@ -0,0 +1,42 @@
+<%#-- copyright
+OpenProject is an open source project management software.
+Copyright (C) the OpenProject GmbH
+
+This program is free software; you can redistribute it and/or
+modify it under the terms of the GNU General Public License version 3.
+
+OpenProject is a fork of ChiliProject, which is a fork of Redmine. The copyright follows:
+Copyright (C) 2006-2013 Jean-Philippe Lang
+Copyright (C) 2010-2013 the ChiliProject Team
+
+This program is free software; you can redistribute it and/or
+modify it under the terms of the GNU General Public License
+as published by the Free Software Foundation; either version 2
+of the License, or (at your option) any later version.
+
+This program is distributed in the hope that it will be useful,
+but WITHOUT ANY WARRANTY; without even the implied warranty of
+MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the
+GNU General Public License for more details.
+
+You should have received a copy of the GNU General Public License
+along with this program; if not, write to the Free Software
+Foundation, Inc., 51 Franklin Street, Fifth Floor, Boston, MA  02110-1301, USA.
+
+See COPYRIGHT and LICENSE files for more details.
+
+++#%>
+
+<%= hidden_field_tag "automation[triggers_attributes][0][type]", "Automations::Triggers::Manual" %>
+<%= hidden_field_tag "automation[triggers_attributes][0][id]", trigger.id if trigger.persisted? %>
+
+<div class="form--field -required">
+  <%= styled_label_tag "automation_triggers_attributes_0_options_button_label", t("automations.triggers.manual.button_label"), class: "-top" %>
+  <div class="form--field-container">
+    <%= styled_text_field_tag "automation[triggers_attributes][0][options][button_label]",
+                              trigger.button_label || @automation.name,
+                              id: "automation_triggers_attributes_0_options_button_label",
+                              container_class: "-middle",
+                              required: true %>
+  </div>
+</div>
diff --git a/app/views/custom_actions/edit.html.erb b/app/views/automations/edit.html.erb
similarity index 83%
rename from app/views/custom_actions/edit.html.erb
rename to app/views/automations/edit.html.erb
index 765b47d7fc99..492d03240ef8 100644
--- a/app/views/custom_actions/edit.html.erb
+++ b/app/views/automations/edit.html.erb
@@ -27,25 +27,25 @@ See COPYRIGHT and LICENSE files for more details.
 
 ++#%>
 
-<% html_title t(:label_administration), t("custom_actions.edit", name: @custom_action.name) %>
+<% html_title t(:label_administration), t("automations.edit", name: @automation.name) %>
 
 <%=
   render Primer::OpenProject::PageHeader.new do |header|
-    header.with_title { @custom_action.name }
+    header.with_title { @automation.name }
     header.with_breadcrumbs(
       [{ href: admin_index_path, text: t("label_administration") },
        { href: admin_settings_work_packages_general_path, text: t(:label_work_package_plural) },
-       { href: custom_actions_path, text: t("custom_actions.plural") },
-       @custom_action.name]
+       { href: automations_path, text: t("automations.plural") },
+       @automation.name]
     )
   end
 %>
 
-<%= error_messages_for @custom_action %>
+<%= error_messages_for @automation %>
 
 <% content_controller "hide-sections" %>
 
-<%= labelled_tabular_form_for @custom_action,
+<%= labelled_tabular_form_for @automation,
                               data: { "hide-sections-target": "form" } do |f| %>
   <%= render partial: "form", locals: { f: f } %>
   <%= styled_button_tag t(:button_save), class: "-primary -with-icon icon-checkmark" %>
diff --git a/app/views/automations/index.html.erb b/app/views/automations/index.html.erb
new file mode 100644
index 000000000000..5a8a3d43b9fb
--- /dev/null
+++ b/app/views/automations/index.html.erb
@@ -0,0 +1,60 @@
+<%#-- copyright
+OpenProject is an open source project management software.
+Copyright (C) the OpenProject GmbH
+
+This program is free software; you can redistribute it and/or
+modify it under the terms of the GNU General Public License version 3.
+
+OpenProject is a fork of ChiliProject, which is a fork of Redmine. The copyright follows:
+Copyright (C) 2006-2013 Jean-Philippe Lang
+Copyright (C) 2010-2013 the ChiliProject Team
+
+This program is free software; you can redistribute it and/or
+modify it under the terms of the GNU General Public License
+as published by the Free Software Foundation; either version 2
+of the License, or (at your option) any later version.
+
+This program is distributed in the hope that it will be useful,
+but WITHOUT ANY WARRANTY; without even the implied warranty of
+MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the
+GNU General Public License for more details.
+
+You should have received a copy of the GNU General Public License
+along with this program; if not, write to the Free Software
+Foundation, Inc., 51 Franklin Street, Fifth Floor, Boston, MA  02110-1301, USA.
+
+See COPYRIGHT and LICENSE files for more details.
+
+++#%>
+
+<% html_title t(:label_administration), t("automations.plural") -%>
+
+<%=
+  render Primer::OpenProject::PageHeader.new do |header|
+    header.with_title { t("automations.plural") }
+    header.with_breadcrumbs(
+      [{ href: admin_index_path, text: t("label_administration") },
+       { href: admin_settings_work_packages_general_path, text: t(:label_work_package_plural) },
+       t("automations.plural")]
+    )
+  end
+%>
+
+<%= with_enterprise_banner_guard(:custom_actions, variant: :large, video: "enterprise/custom-actions.mp4") do %>
+  <%=
+    render(Primer::OpenProject::SubHeader.new) do |subheader|
+      subheader.with_action_button(
+        scheme: :primary,
+        leading_icon: :plus,
+        label: t("automations.new"),
+        test_selector: "op-admin-automations--button-new",
+        tag: :a,
+        disabled: !EnterpriseToken.allows_to?(:custom_actions),
+        href: new_automation_path
+      ) do
+        Automation.model_name.human
+      end
+    end
+  %>
+  <%= render(::Automations::IndexComponent.new(rows: @automations)) %>
+<% end %>
diff --git a/app/views/custom_actions/new.html.erb b/app/views/automations/new.html.erb
similarity index 84%
rename from app/views/custom_actions/new.html.erb
rename to app/views/automations/new.html.erb
index ce3f147df66b..43207b0590cc 100644
--- a/app/views/custom_actions/new.html.erb
+++ b/app/views/automations/new.html.erb
@@ -27,25 +27,25 @@ See COPYRIGHT and LICENSE files for more details.
 
 ++#%>
 
-<% html_title t(:label_administration), t("custom_actions.new") %>
+<% html_title t(:label_administration), t("automations.new") %>
 
 <%=
   render Primer::OpenProject::PageHeader.new do |header|
-    header.with_title { t("custom_actions.new") }
+    header.with_title { t("automations.new") }
     header.with_breadcrumbs(
       [{ href: admin_index_path, text: t("label_administration") },
        { href: admin_settings_work_packages_general_path, text: t(:label_work_package_plural) },
-       { href: custom_actions_path, text: t("custom_actions.plural") },
-       t("custom_actions.new")]
+       { href: automations_path, text: t("automations.plural") },
+       t("automations.new")]
     )
   end
 %>
 
-<%= error_messages_for @custom_action %>
+<%= error_messages_for @automation %>
 
 <% content_controller "hide-sections" %>
 
-<%= labelled_tabular_form_for @custom_action,
+<%= labelled_tabular_form_for @automation,
                               data: { "hide-sections-target": "form" } do |f| %>
   <%= render partial: "form", locals: { f: f } %>
   <%= styled_button_tag t(:button_create), class: "-primary -with-icon icon-checkmark" %>
diff --git a/app/views/custom_actions/index.html.erb b/app/views/custom_actions/index.html.erb
deleted file mode 100644
index d1239f92b944..000000000000
--- a/app/views/custom_actions/index.html.erb
+++ /dev/null
@@ -1,31 +0,0 @@
-<% html_title t(:label_administration), t("custom_actions.plural") -%>
-
-<%=
-  render Primer::OpenProject::PageHeader.new do |header|
-    header.with_title { t("custom_actions.plural") }
-    header.with_breadcrumbs(
-      [{ href: admin_index_path, text: t("label_administration") },
-       { href: admin_settings_work_packages_general_path, text: t(:label_work_package_plural) },
-       t("custom_actions.plural")]
-    )
-  end
-%>
-
-<%= with_enterprise_banner_guard(:custom_actions, variant: :large, video: "enterprise/custom-actions.mp4") do %>
-  <%=
-    render(Primer::OpenProject::SubHeader.new) do |subheader|
-      subheader.with_action_button(
-        scheme: :primary,
-        leading_icon: :plus,
-        label: t("custom_actions.new"),
-        test_selector: "op-admin-custom-actions--button-new",
-        tag: :a,
-        disabled: !EnterpriseToken.allows_to?(:custom_actions),
-        href: new_custom_action_path
-      ) do
-        CustomAction.model_name.human
-      end
-    end
-  %>
-  <%= render(::CustomActions::TableComponent.new(rows: @custom_actions)) %>
-<% end %>
diff --git a/config/initializers/menus.rb b/config/initializers/menus.rb
index 66c679e2a4cb..783961bdd8d1 100644
--- a/config/initializers/menus.rb
+++ b/config/initializers/menus.rb
@@ -479,10 +479,10 @@
             icon: "op-custom-fields",
             html: { class: "custom_fields" }
 
-  menu.push :custom_actions,
-            { controller: "/custom_actions" },
+  menu.push :automations,
+            { controller: "/automations" },
             if: ->(_) { User.current.admin? },
-            caption: :"custom_actions.plural",
+            caption: :"automations.plural",
             parent: :admin_work_packages,
             enterprise_feature: "custom_actions"
 
diff --git a/config/locales/en.yml b/config/locales/en.yml
index 4af42f975241..6ebd9c780384 100644
--- a/config/locales/en.yml
+++ b/config/locales/en.yml
@@ -2137,6 +2137,7 @@ en:
     groups: "Groups"
     hexcode: "Hex code"
     id: "ID"
+    inexistent: "Inexistent"
     is_default: "Default value"
     is_for_all: "For all projects"
     # kept for backwards compatibility
@@ -2199,6 +2200,29 @@ en:
   authentication:
     login_and_registration: "Login and registration"
 
+  automations:
+    actions:
+      add: "Add action"
+      assigned_to:
+        executing_user_value: "(Assign to executing user)"
+      name: "Actions"
+    conditions: "Conditions"
+    edit: "Edit automation %{name}"
+    new: "New automation"
+    plural: "Automations"
+    summary:
+      if: "If"
+      none: "None"
+      then: "Then"
+      title: "Summary"
+      when: "When"
+    trigger: "Trigger"
+    triggers:
+      manual:
+        button_label: "Button label"
+        label: "Manual button click"
+      name: "Triggers"
+
   background_jobs:
     status:
       cancelled_due_to: "Job was cancelled due to error: %{message}"
diff --git a/config/routes.rb b/config/routes.rb
index da8a35663eef..d574bdf9c1f1 100644
--- a/config/routes.rb
+++ b/config/routes.rb
@@ -780,7 +780,7 @@
       end
     end
 
-    resources :custom_actions, except: :show
+    resources :automations, except: :show
 
     namespace :oauth do
       resources :applications do
diff --git a/db/migrate/20260907113318_convert_custom_actions_to_automations.rb b/db/migrate/20260907113318_convert_custom_actions_to_automations.rb
new file mode 100644
index 000000000000..1703a031afd6
--- /dev/null
+++ b/db/migrate/20260907113318_convert_custom_actions_to_automations.rb
@@ -0,0 +1,115 @@
+# frozen_string_literal: true
+
+#-- copyright
+# OpenProject is an open source project management software.
+# Copyright (C) the OpenProject GmbH
+#
+# This program is free software; you can redistribute it and/or
+# modify it under the terms of the GNU General Public License version 3.
+#
+# OpenProject is a fork of ChiliProject, which is a fork of Redmine. The copyright follows:
+# Copyright (C) 2006-2013 Jean-Philippe Lang
+# Copyright (C) 2010-2013 the ChiliProject Team
+#
+# This program is free software; you can redistribute it and/or
+# modify it under the terms of the GNU General Public License
+# as published by the Free Software Foundation; either version 2
+# of the License, or (at your option) any later version.
+#
+# This program is distributed in the hope that it will be useful,
+# but WITHOUT ANY WARRANTY; without even the implied warranty of
+# MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the
+# GNU General Public License for more details.
+#
+# You should have received a copy of the GNU General Public License
+# along with this program; if not, write to the Free Software
+# Foundation, Inc., 51 Franklin Street, Fifth Floor, Boston, MA  02110-1301, USA.
+#
+# See COPYRIGHT and LICENSE files for more details.
+#++
+
+require Rails.root.join("db/migrate/migration_utils/utils")
+
+class ConvertCustomActionsToAutomations < ActiveRecord::Migration[8.1]
+  include Migration::Utils
+
+  JOIN_TABLES = {
+    statuses: :status_id,
+    roles: :role_id,
+    types: :type_id,
+    projects: :project_id
+  }.freeze
+
+  class MigrationAutomation < ApplicationRecord
+    self.table_name = "automations"
+  end
+
+  class MigrationTrigger < ApplicationRecord
+    self.table_name = "automation_triggers"
+    self.inheritance_column = nil
+  end
+
+  def up
+    rename_table :custom_actions, :automations
+
+    JOIN_TABLES.each do |suffix, other_column|
+      rename_join_table(:"custom_actions_#{suffix}", :"automations_#{suffix}",
+                        :custom_action_id, :automation_id, other_column)
+    end
+
+    create_table :automation_triggers do |t|
+      t.references :automation, null: false, foreign_key: true, index: true
+      t.string :type, null: false
+      t.jsonb :options, null: false, default: {}
+      t.integer :position
+
+      t.timestamps
+    end
+
+    MigrationAutomation.reset_column_information
+    MigrationTrigger.reset_column_information
+
+    MigrationAutomation.find_each do |automation|
+      MigrationTrigger.create!(
+        automation_id: automation.id,
+        type: "Automations::Triggers::Manual",
+        options: { button_label: automation.name },
+        position: 1
+      )
+    end
+  end
+
+  def down
+    drop_table :automation_triggers
+
+    JOIN_TABLES.reverse_each do |suffix, other_column|
+      rename_join_table(:"automations_#{suffix}", :"custom_actions_#{suffix}",
+                        :automation_id, :custom_action_id, other_column)
+    end
+
+    rename_table :automations, :custom_actions
+  end
+
+  private
+
+  # rename_table and rename_column already take care of renaming the Rails-default indexes.
+  # So we only have to normalize possibly remaining indexes here
+  def rename_join_table(from_table, to_table, old_fk, new_fk, other_column)
+    rename_table from_table, to_table
+    rename_column to_table, old_fk, new_fk
+
+    normalize_index to_table, "index_#{from_table}_on_#{old_fk}", "index_#{to_table}_on_#{new_fk}", new_fk
+    normalize_index to_table, "index_#{from_table}_on_#{other_column}", "index_#{to_table}_on_#{other_column}",
+                    other_column
+  end
+
+  def normalize_index(table, legacy_name, canonical_name, column)
+    actual_name = resolved_index_name(table, legacy_name, [column])
+
+    if actual_name.nil?
+      add_index table, column, name: canonical_name
+    elsif actual_name != canonical_name
+      rename_index table, actual_name, canonical_name
+    end
+  end
+end
diff --git a/lib/api/v3/custom_actions/custom_action_representer.rb b/lib/api/v3/custom_actions/custom_action_representer.rb
index 29328e861578..d5204ecc73df 100644
--- a/lib/api/v3/custom_actions/custom_action_representer.rb
+++ b/lib/api/v3/custom_actions/custom_action_representer.rb
@@ -1,3 +1,5 @@
+# frozen_string_literal: true
+
 #-- copyright
 # OpenProject is an open source project management software.
 # Copyright (C) the OpenProject GmbH
@@ -33,7 +35,7 @@ class CustomActionRepresenter < ::API::Decorators::Single
         link :executeImmediately do
           {
             href: api_v3_paths.custom_action_execute(represented.id),
-            title: I18n.t("custom_actions.execute", name: represented.name),
+            title: I18n.t("custom_actions.execute", name: name),
             method: "post"
           }
         end
@@ -44,6 +46,11 @@ class CustomActionRepresenter < ::API::Decorators::Single
         property :description,
                  render_nil: true
 
+        def name
+          trigger = represented.triggers.detect { |trigger| trigger.is_a?(::Automations::Triggers::Manual) }
+          trigger&.button_label || represented.name
+        end
+
         def _type
           "CustomAction"
         end
diff --git a/lib/api/v3/custom_actions/custom_actions_api.rb b/lib/api/v3/custom_actions/custom_actions_api.rb
index 9bcb30992ef9..931903360a7b 100644
--- a/lib/api/v3/custom_actions/custom_actions_api.rb
+++ b/lib/api/v3/custom_actions/custom_actions_api.rb
@@ -34,7 +34,7 @@ class CustomActionsAPI < ::API::OpenProjectAPI
           route_param :id, type: Integer, desc: "Custom action ID" do
             helpers do
               def custom_action
-                @custom_action ||= CustomAction.find(params[:id])
+                @custom_action ||= Automation.with_manual_trigger.find(params[:id])
               end
             end
 
@@ -63,8 +63,8 @@ def parsed_params
               end
 
               after_validation do
-                contract = ::CustomActions::ExecuteContract.new(parsed_params, current_user,
-                                                                options: { custom_action: })
+                contract = ::Automations::ExecuteContract.new(parsed_params, current_user,
+                                                              options: { automation: custom_action })
 
                 unless contract.valid?
                   fail ::API::Errors::ErrorBase.create_and_merge_errors(contract.errors)
@@ -75,7 +75,7 @@ def parsed_params
                 work_package = WorkPackage.visible.find_by(id: parsed_params.work_package_id)
                 work_package.lock_version = parsed_params.lock_version
 
-                ::CustomActions::UpdateWorkPackageService
+                ::Automations::UpdateWorkPackageService
                   .new(user: current_user,
                        action: custom_action)
                   .call(work_package:) do |call|
diff --git a/lib/api/v3/work_packages/eager_loading/custom_action.rb b/lib/api/v3/work_packages/eager_loading/automation.rb
similarity index 61%
rename from lib/api/v3/work_packages/eager_loading/custom_action.rb
rename to lib/api/v3/work_packages/eager_loading/automation.rb
index 4a12af1d7a8d..ada1803f8bac 100644
--- a/lib/api/v3/work_packages/eager_loading/custom_action.rb
+++ b/lib/api/v3/work_packages/eager_loading/automation.rb
@@ -1,3 +1,5 @@
+# frozen_string_literal: true
+
 #-- copyright
 # OpenProject is an open source project management software.
 # Copyright (C) the OpenProject GmbH
@@ -30,40 +32,43 @@ module API
   module V3
     module WorkPackages
       module EagerLoading
-        class CustomAction < Base
+        class Automation < Base
           def apply(work_package)
-            applicable_actions = custom_actions.select do |action|
-              action.conditions_fulfilled?(work_package, User.current)
+            applicable_automations = automations.select do |automation|
+              automation.conditions_fulfilled?(work_package, User.current)
             end
 
-            work_package.custom_actions = applicable_actions
+            work_package.automations = applicable_automations
           end
 
           def self.module
-            CustomActionAccessor
+            AutomationAccessor
           end
 
           private
 
-          def custom_actions
-            @custom_actions ||= ::CustomAction
-                                .available_conditions
-                                .inject(::CustomAction.all) do |scope, condition|
-              scope.merge(condition.custom_action_scope(work_packages, User.current))
+          def automations
+            @automations ||= ::Automation
+                             .available_conditions
+                             .inject(::Automation.with_manual_trigger.includes(:triggers)) do |scope, condition|
+              scope.merge(condition.automation_scope(work_packages, User.current))
             end
           end
 
-          module CustomActionAccessor
+          module AutomationAccessor
             extend ActiveSupport::Concern
 
             included do
-              attr_writer :custom_actions
+              attr_writer :automations
 
-              # Hiding the work_package's own custom_actions method
-              # to profit from the eager loaded actions
-              def custom_actions(_user)
-                @custom_actions
+              # Hiding the work_package's own automations method
+              # to profit from the eager loaded automations
+              def automations(_user)
+                @automations
               end
+
+              # API compatibility for /api/v3/custom_actions
+              def custom_actions(user) = automations(user)
             end
           end
         end
diff --git a/lib/api/v3/work_packages/work_package_eager_loading_wrapper.rb b/lib/api/v3/work_packages/work_package_eager_loading_wrapper.rb
index 79c41206e8be..da7ff6363a2b 100644
--- a/lib/api/v3/work_packages/work_package_eager_loading_wrapper.rb
+++ b/lib/api/v3/work_packages/work_package_eager_loading_wrapper.rb
@@ -78,7 +78,7 @@ def eager_loader_classes_all
               ::API::V3::WorkPackages::EagerLoading::Principals,
               ::API::V3::WorkPackages::EagerLoading::Checksum,
               ::API::V3::WorkPackages::EagerLoading::CustomValue,
-              ::API::V3::WorkPackages::EagerLoading::CustomAction,
+              ::API::V3::WorkPackages::EagerLoading::Automation,
               # Have the historic attributes last as they require the custom values
               # to be loaded first in order to create the diffs between the current
               # and the historic values without loading the custom fields (Acts::Journalized::Differ).
diff --git a/spec/contracts/custom_actions/cu_contract_spec.rb b/spec/contracts/automations/cu_contract_spec.rb
similarity index 81%
rename from spec/contracts/custom_actions/cu_contract_spec.rb
rename to spec/contracts/automations/cu_contract_spec.rb
index 4a87e4dafebb..e2ab078276d6 100644
--- a/spec/contracts/custom_actions/cu_contract_spec.rb
+++ b/spec/contracts/automations/cu_contract_spec.rb
@@ -31,15 +31,15 @@
 require "spec_helper"
 require "contracts/shared/model_contract_shared_context"
 
-RSpec.describe CustomActions::CuContract do
+RSpec.describe Automations::CuContract do
   include_context "ModelContract shared context"
 
   let(:user) { build_stubbed(:user) }
   let(:action) do
-    build_stubbed(:custom_action, actions:
-                              [CustomActions::Actions::AssignedTo.new])
+    build_stubbed(:automation, actions:
+                              [Automations::Actions::AssignedTo.new])
   end
-  let(:contract) { described_class.new(action) }
+  let(:contract) { described_class.new(action, user) }
 
   describe "name" do
     it "is writable" do
@@ -65,7 +65,7 @@
 
   describe "actions" do
     it "is writable" do
-      responsible_action = CustomActions::Actions::Responsible.new
+      responsible_action = Automations::Actions::Responsible.new
 
       action.actions = [responsible_action]
 
@@ -79,13 +79,13 @@
     end
 
     it "requires a value if the action requires one" do
-      action.actions = [CustomActions::Actions::Status.new([])]
+      action.actions = [Automations::Actions::Status.new([])]
 
       expect_contract_invalid actions: :empty
     end
 
     it "allows only the allowed values" do
-      status_action = CustomActions::Actions::Status.new([0])
+      status_action = Automations::Actions::Status.new([0])
       allow(status_action)
         .to receive(:allowed_values)
         .and_return([{ value: nil, label: "-" },
@@ -97,7 +97,7 @@
     end
 
     it "is not allowed to have an inexistent action" do
-      action.actions = [CustomActions::Actions::Inexistent.new]
+      action.actions = [Automations::Actions::Inexistent.new]
 
       expect_contract_invalid actions: :does_not_exist
     end
@@ -105,14 +105,14 @@
 
   describe "conditions" do
     it "is writable" do
-      action.conditions = [double("some bogus condition", key: "some", values: "bogus", validate: true)]
+      action.conditions = [instance_double(Automations::Conditions::Base, key: "some", values: "bogus", validate: true)]
 
       expect(contract.validate)
         .to be_truthy
     end
 
     it "allows only the allowed values" do
-      status_condition = CustomActions::Conditions::Status.new([0])
+      status_condition = Automations::Conditions::Status.new([0])
       allow(status_condition)
         .to receive(:allowed_values)
         .and_return([{ value: nil, label: "-" },
@@ -124,7 +124,7 @@
     end
 
     it "is not allowed to have an inexistent condition" do
-      action.conditions = [CustomActions::Conditions::Inexistent.new]
+      action.conditions = [Automations::Conditions::Inexistent.new]
 
       expect_contract_invalid conditions: :does_not_exist
     end
diff --git a/spec/controllers/custom_actions_controller_spec.rb b/spec/controllers/automations_controller_spec.rb
similarity index 85%
rename from spec/controllers/custom_actions_controller_spec.rb
rename to spec/controllers/automations_controller_spec.rb
index e3473ab68a62..147d0db1eac8 100644
--- a/spec/controllers/custom_actions_controller_spec.rb
+++ b/spec/controllers/automations_controller_spec.rb
@@ -30,13 +30,13 @@
 
 require "spec_helper"
 
-RSpec.describe CustomActionsController, with_ee: %i[custom_actions] do
+RSpec.describe AutomationsController, with_ee: %i[custom_actions] do
   let(:admin) { build(:admin) }
   let(:non_admin) { build(:user) }
-  let(:action) { build_stubbed(:custom_action) }
+  let(:action) { build_stubbed(:automation) }
   let(:params) do
-    { custom_action: { name: "blubs",
-                       actions: { assigned_to: 1 } } }
+    { automation: { name: "blubs",
+                    actions: { assigned_to: 1 } } }
   end
 
   shared_examples_for "requires enterprise token" do
@@ -70,12 +70,7 @@
 
   describe "#index" do
     let(:call) { get :index }
-
-    before do
-      allow(CustomAction)
-        .to receive(:order_by_position)
-        .and_return([action])
-    end
+    let!(:automation) { create(:automation) }
 
     context "for admins" do
       before do
@@ -94,9 +89,9 @@
           .to render_template("index")
       end
 
-      it "assigns the custom actions" do
-        expect(assigns(:custom_actions))
-          .to contain_exactly(action)
+      it "assigns the automations" do
+        expect(assigns(:automations))
+          .to contain_exactly(automation)
       end
     end
 
@@ -122,7 +117,7 @@
       before do
         login_as(admin)
 
-        allow(CustomAction)
+        allow(Automation)
           .to receive(:new)
           .and_return(action)
 
@@ -139,8 +134,8 @@
           .to render_template("new")
       end
 
-      it "assigns custom_action" do
-        expect(assigns(:custom_action))
+      it "assigns automation" do
+        expect(assigns(:automation))
           .to eql action
       end
     end
@@ -156,14 +151,14 @@
     let(:permitted_params) do
       ActionController::Parameters
         .new(params)
-        .require(:custom_action)
+        .require(:automation)
         .permit(:name)
         .merge(ActionController::Parameters.new(actions: { assigned_to: "1" }).permit!)
     end
     let!(:service) do
-      service = double("create service")
+      service = instance_double(Automations::CreateService)
 
-      allow(CustomActions::CreateService)
+      allow(Automations::CreateService)
         .to receive(:new)
         .with(user: admin)
         .and_return(service)
@@ -190,7 +185,7 @@
       context "on success" do
         it "redirects to index" do
           expect(response)
-            .to redirect_to(custom_actions_path)
+            .to redirect_to(automations_path)
         end
       end
 
@@ -203,7 +198,7 @@
         end
 
         it "assigns custom action" do
-          expect(assigns[:custom_action])
+          expect(assigns[:automation])
             .to eql action
         end
       end
@@ -222,7 +217,7 @@
     end
 
     before do
-      allow(CustomAction)
+      allow(Automation)
         .to receive(:find)
         .with(params[:id])
         .and_return(action)
@@ -245,15 +240,15 @@
           .to render_template("edit")
       end
 
-      it "assigns custom_action" do
-        expect(assigns(:custom_action))
+      it "assigns automation" do
+        expect(assigns(:automation))
           .to eql action
       end
     end
 
     context "for admins on invalid id" do
       before do
-        allow(CustomAction)
+        allow(Automation)
           .to receive(:find)
           .with(params[:id])
           .and_raise(ActiveRecord::RecordNotFound)
@@ -280,19 +275,19 @@
     let(:permitted_params) do
       ActionController::Parameters
         .new(params)
-        .require(:custom_action)
+        .require(:automation)
         .permit(:name)
         .merge(ActionController::Parameters.new(actions: { assigned_to: "1" }).permit!)
     end
     let(:params) do
-      { custom_action: { name: "blubs",
-                         actions: { assigned_to: 1 } },
+      { automation: { name: "blubs",
+                      actions: { assigned_to: 1 } },
         id: "42" }
     end
     let!(:service) do
-      service = double("update service")
+      service = instance_double(Automations::UpdateService)
 
-      allow(CustomActions::UpdateService)
+      allow(Automations::UpdateService)
         .to receive(:new)
         .with(user: admin, action:)
         .and_return(service)
@@ -310,7 +305,7 @@
     end
 
     before do
-      allow(CustomAction)
+      allow(Automation)
         .to receive(:find)
         .with(params[:id])
         .and_return(action)
@@ -326,7 +321,7 @@
       context "on success" do
         it "redirects to index" do
           expect(response)
-            .to redirect_to(custom_actions_path)
+            .to redirect_to(automations_path)
         end
       end
 
@@ -339,7 +334,7 @@
         end
 
         it "assigns the action" do
-          expect(assigns[:custom_action])
+          expect(assigns[:automation])
             .to eql(action)
         end
       end
@@ -347,7 +342,7 @@
 
     context "for admins on invalid id" do
       before do
-        allow(CustomAction)
+        allow(Automation)
           .to receive(:find)
           .with(params[:id])
           .and_raise(ActiveRecord::RecordNotFound)
@@ -375,7 +370,7 @@
     end
 
     before do
-      allow(CustomAction)
+      allow(Automation)
         .to receive(:find)
         .with(params[:id])
         .and_return(action)
@@ -383,8 +378,8 @@
 
     context "for admins" do
       before do
-        expect(action)
-          .to receive(:destroy)
+        allow(action)
+          .to receive(:destroy!)
           .and_return(true)
 
         login_as(current_user)
@@ -392,15 +387,20 @@
         call
       end
 
+      it "destroys the automation" do
+        expect(action)
+          .to have_received(:destroy!)
+      end
+
       it "redirects to index" do
         expect(response)
-          .to redirect_to(custom_actions_path)
+          .to redirect_to(automations_path)
       end
     end
 
     context "for admins on invalid id" do
       before do
-        allow(CustomAction)
+        allow(Automation)
           .to receive(:find)
           .with(params[:id])
           .and_raise(ActiveRecord::RecordNotFound)
@@ -419,7 +419,7 @@
     context "for admins without an enterprise token", with_ee: false do
       before do
         allow(action)
-          .to receive(:destroy)
+          .to receive(:destroy!)
           .and_return(true)
 
         login_as(admin)
@@ -429,7 +429,7 @@
 
       it "redirects to index" do
         expect(response).to redirect_to action: :index
-        expect(action).to have_received(:destroy)
+        expect(action).to have_received(:destroy!)
       end
     end
 
diff --git a/spec/factories/automation_factory.rb b/spec/factories/automation_factory.rb
new file mode 100644
index 000000000000..a6a1ee441ca2
--- /dev/null
+++ b/spec/factories/automation_factory.rb
@@ -0,0 +1,51 @@
+# frozen_string_literal: true
+
+#-- copyright
+# OpenProject is an open source project management software.
+# Copyright (C) the OpenProject GmbH
+#
+# This program is free software; you can redistribute it and/or
+# modify it under the terms of the GNU General Public License version 3.
+#
+# OpenProject is a fork of ChiliProject, which is a fork of Redmine. The copyright follows:
+# Copyright (C) 2006-2013 Jean-Philippe Lang
+# Copyright (C) 2010-2013 the ChiliProject Team
+#
+# This program is free software; you can redistribute it and/or
+# modify it under the terms of the GNU General Public License
+# as published by the Free Software Foundation; either version 2
+# of the License, or (at your option) any later version.
+#
+# This program is distributed in the hope that it will be useful,
+# but WITHOUT ANY WARRANTY; without even the implied warranty of
+# MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the
+# GNU General Public License for more details.
+#
+# You should have received a copy of the GNU General Public License
+# along with this program; if not, write to the Free Software
+# Foundation, Inc., 51 Franklin Street, Fifth Floor, Boston, MA  02110-1301, USA.
+#
+# See COPYRIGHT and LICENSE files for more details.
+#++
+
+FactoryBot.define do
+  factory :automation do
+    sequence(:name) { |n| "Custom action #{n} - name" }
+    sequence(:description) { |n| "Custom action #{n} - description" }
+
+    after(:build) do |automation|
+      next if automation.triggers.any?(Automations::Triggers::Manual)
+
+      automation.triggers << build(:manual_trigger, automation:)
+    end
+
+    trait :with_manual_trigger
+  end
+
+  factory :manual_trigger, class: "Automations::Triggers::Manual" do
+    automation
+    button_label { "Run automation" }
+  end
+
+  factory :automation_with_manual_trigger, parent: :automation
+end
diff --git a/spec/features/work_packages/custom_actions/custom_actions_link_value_spec.rb b/spec/features/work_packages/automations/automations_link_value_spec.rb
similarity index 88%
rename from spec/features/work_packages/custom_actions/custom_actions_link_value_spec.rb
rename to spec/features/work_packages/automations/automations_link_value_spec.rb
index 8bd29bb4279d..952f7b4885f1 100644
--- a/spec/features/work_packages/custom_actions/custom_actions_link_value_spec.rb
+++ b/spec/features/work_packages/automations/automations_link_value_spec.rb
@@ -30,7 +30,7 @@
 
 require "spec_helper"
 
-RSpec.describe "Custom actions link cf value", :js, with_ee: %i[custom_actions] do
+RSpec.describe "Automations link cf value", :js, with_ee: %i[custom_actions] do
   shared_let(:admin) { create(:admin) }
 
   let(:permissions) { %i(view_work_packages edit_work_packages) }
@@ -51,7 +51,7 @@
   let(:default_priority) do
     create(:default_priority, name: "Normal")
   end
-  let(:new_ca_page) { Pages::Admin::CustomActions::New.new }
+  let(:new_ca_page) { Pages::Admin::Automations::New.new }
 
   before do
     login_as(admin)
@@ -61,11 +61,12 @@
     new_ca_page.visit!
 
     new_ca_page.set_name("Set Link CF")
+    new_ca_page.set_button_label("Set Link CF")
     new_ca_page.add_action(custom_field.name, "https://example.com")
 
     new_ca_page.create
 
-    assign = CustomAction.last
+    assign = Automation.last
     expect(assign.actions.length).to eq(1)
     expect(assign.conditions.length).to eq(0)
     expect(assign.actions.first.values).to eq(["https://example.com"])
@@ -73,8 +74,8 @@
     login_as user
     wp_page.visit!
 
-    wp_page.expect_custom_action("Set Link CF")
-    wp_page.click_custom_action("Set Link CF")
+    wp_page.expect_automation("Set Link CF")
+    wp_page.click_automation("Set Link CF")
     wp_page.expect_attributes "customField#{custom_field.id}": "https://example.com"
   end
 end
diff --git a/spec/features/work_packages/custom_actions/custom_actions_me_value_spec.rb b/spec/features/work_packages/automations/automations_me_value_spec.rb
similarity index 85%
rename from spec/features/work_packages/custom_actions/custom_actions_me_value_spec.rb
rename to spec/features/work_packages/automations/automations_me_value_spec.rb
index 30473b9f170f..d56878461647 100644
--- a/spec/features/work_packages/custom_actions/custom_actions_me_value_spec.rb
+++ b/spec/features/work_packages/automations/automations_me_value_spec.rb
@@ -30,7 +30,7 @@
 
 require "spec_helper"
 
-RSpec.describe "Custom actions me value", :js, with_ee: %i[custom_actions] do
+RSpec.describe "Automations me value", :js, with_ee: %i[custom_actions] do
   shared_let(:admin) { create(:admin) }
 
   let(:permissions) { %i(view_work_packages edit_work_packages) }
@@ -51,7 +51,7 @@
   let(:default_priority) do
     create(:default_priority, name: "Normal")
   end
-  let(:index_ca_page) { Pages::Admin::CustomActions::Index.new }
+  let(:index_ca_page) { Pages::Admin::Automations::Index.new }
 
   before do
     login_as(admin)
@@ -63,11 +63,12 @@
 
     new_ca_page = index_ca_page.new
     new_ca_page.set_name("Set CF to me")
-    new_ca_page.add_action(custom_field.name, I18n.t("custom_actions.actions.assigned_to.executing_user_value"))
+    new_ca_page.set_button_label("Set CF to me")
+    new_ca_page.add_action(custom_field.name, I18n.t("automations.actions.assigned_to.executing_user_value"))
 
     new_ca_page.create
 
-    assign = CustomAction.last
+    assign = Automation.last
     expect(assign.actions.length).to eq(1)
     expect(assign.conditions.length).to eq(0)
     expect(assign.actions.first.values).to eq(["current_user"])
@@ -75,8 +76,8 @@
     login_as user
     wp_page.visit!
 
-    wp_page.expect_custom_action("Set CF to me")
-    wp_page.click_custom_action("Set CF to me")
+    wp_page.expect_automation("Set CF to me")
+    wp_page.click_automation("Set CF to me")
     wp_page.expect_attributes "customField#{custom_field.id}": user.name
   end
 end
diff --git a/spec/features/work_packages/custom_actions/custom_actions_spec.rb b/spec/features/work_packages/automations/automations_spec.rb
similarity index 83%
rename from spec/features/work_packages/custom_actions/custom_actions_spec.rb
rename to spec/features/work_packages/automations/automations_spec.rb
index 2d8ba74e9c1d..5a78e77ab414 100644
--- a/spec/features/work_packages/custom_actions/custom_actions_spec.rb
+++ b/spec/features/work_packages/automations/automations_spec.rb
@@ -30,7 +30,7 @@
 
 require "spec_helper"
 
-RSpec.describe "Custom actions", :js, with_ee: %i[custom_actions] do
+RSpec.describe "Automations", :js, with_ee: %i[custom_actions] do
   shared_let(:admin) { create(:admin) }
 
   shared_let(:permissions) { %i(view_work_packages edit_work_packages move_work_packages work_package_assigned) }
@@ -135,7 +135,7 @@
       work_package.type.default_variant.custom_fields << cf
     end
   end
-  let(:index_ca_page) { Pages::Admin::CustomActions::Index.new }
+  let(:index_ca_page) { Pages::Admin::Automations::Index.new }
   let(:activity_tab) { Components::WorkPackages::Activities.new(work_package) }
 
   before do
@@ -152,6 +152,7 @@
     new_ca_page = index_ca_page.new
 
     new_ca_page.set_name("Unassign")
+    new_ca_page.set_button_label("Unassign")
     new_ca_page.set_description("Removes the assignee")
     new_ca_page.add_action("Assignee", "-")
     new_ca_page.expect_action("assigned_to", nil)
@@ -161,7 +162,7 @@
     index_ca_page.expect_current_path
     index_ca_page.expect_listed("Unassign")
 
-    unassign = CustomAction.last
+    unassign = Automation.last
     expect(unassign.actions.length).to eq(1)
     expect(unassign.conditions.length).to eq(0)
 
@@ -170,6 +171,7 @@
     new_ca_page = index_ca_page.new
 
     new_ca_page.set_name("Close")
+    new_ca_page.set_button_label("Close")
 
     new_ca_page.add_action("Status", "Close")
     new_ca_page.expect_action("status", closed_status.id)
@@ -186,7 +188,7 @@
     index_ca_page.expect_current_path
     index_ca_page.expect_listed("Unassign", "Close")
 
-    close = CustomAction.last
+    close = Automation.last
     expect(close.actions.length).to eq(1)
     expect(close.conditions.length).to eq(2)
 
@@ -194,6 +196,7 @@
 
     new_ca_page = index_ca_page.new
     new_ca_page.set_name("Escalate")
+    new_ca_page.set_button_label("Escalate")
     new_ca_page.add_action("Priority", immediate_priority.name)
     new_ca_page.expect_action("priority", immediate_priority.id)
 
@@ -210,7 +213,7 @@
     index_ca_page.expect_current_path
     index_ca_page.expect_listed("Unassign", "Close", "Escalate")
 
-    escalate = CustomAction.last
+    escalate = Automation.last
     expect(escalate.actions.length).to eq(3)
     expect(escalate.conditions.length).to eq(0)
 
@@ -219,6 +222,7 @@
     new_ca_page = index_ca_page.new
 
     new_ca_page.set_name("Reset")
+    new_ca_page.set_button_label("Reset")
 
     new_ca_page.add_action("Priority", default_priority.name)
     new_ca_page.expect_action("priority", default_priority.id)
@@ -241,7 +245,7 @@
     index_ca_page.expect_current_path
     index_ca_page.expect_listed("Unassign", "Close", "Escalate", "Reset")
 
-    reset = CustomAction.last
+    reset = Automation.last
     expect(reset.actions.length).to eq(4)
     expect(reset.conditions.length).to eq(1)
 
@@ -250,6 +254,7 @@
     new_ca_page = index_ca_page.new
 
     new_ca_page.set_name("Other roles action")
+    new_ca_page.set_button_label("Other roles action")
 
     new_ca_page.add_action("Status", default_status.name)
     new_ca_page.expect_action("status", default_status.id)
@@ -261,7 +266,7 @@
     index_ca_page.expect_current_path
     index_ca_page.expect_listed("Unassign", "Close", "Escalate", "Reset", "Other roles action")
 
-    other_roles_action = CustomAction.last
+    other_roles_action = Automation.last
     expect(other_roles_action.actions.length).to eq(1)
     expect(other_roles_action.conditions.length).to eq(1)
 
@@ -271,6 +276,7 @@
 
     retry_block do
       new_ca_page.set_name("Move project")
+      new_ca_page.set_button_label("Move project")
       # Add date custom action which has a different admin layout
 
       ignore_ferrum_javascript_error do
@@ -282,7 +288,7 @@
       end
 
       date = (Date.current + 5.days)
-      find("#custom_action_actions_custom_field_#{date_custom_field.id}_visible").click
+      find("#automation_actions_custom_field_#{date_custom_field.id}_visible").click
       datepicker = Components::Datepicker.new "body"
       datepicker.set_date date
 
@@ -301,7 +307,7 @@
     index_ca_page.expect_current_path
     index_ca_page.expect_listed("Unassign", "Close", "Escalate", "Reset", "Other roles action", "Move project")
 
-    move_project = CustomAction.last
+    move_project = Automation.last
     expect(move_project.actions.length).to eq(3)
     expect(move_project.conditions.length).to eq(1)
 
@@ -310,13 +316,13 @@
 
     wp_page.visit!
 
-    wp_page.expect_custom_action("Unassign")
-    wp_page.expect_custom_action("Close")
-    wp_page.expect_custom_action("Escalate")
-    wp_page.expect_custom_action("Move project")
-    wp_page.expect_no_custom_action("Reset")
-    wp_page.expect_no_custom_action("Other roles action")
-    wp_page.expect_custom_action_order("Unassign", "Close", "Escalate", "Move project")
+    wp_page.expect_automation("Unassign")
+    wp_page.expect_automation("Close")
+    wp_page.expect_automation("Escalate")
+    wp_page.expect_automation("Move project")
+    wp_page.expect_no_automation("Reset")
+    wp_page.expect_no_automation("Other roles action")
+    wp_page.expect_automation_order("Unassign", "Close", "Escalate", "Move project")
 
     within(".custom-actions") do
       # When hovering over the button, the description is displayed
@@ -324,11 +330,11 @@
         .to have_button("Unassign", title: "Removes the assignee")
     end
 
-    wp_page.click_custom_action("Unassign")
+    wp_page.click_automation("Unassign")
     wp_page.expect_attributes assignee: "-"
     activity_tab.expect_journal_details_header(text: user.name)
 
-    wp_page.click_custom_action("Escalate")
+    wp_page.click_automation("Escalate")
     wp_page.expect_attributes priority: immediate_priority.name,
                               status: default_status.name,
                               assignee: "-",
@@ -336,14 +342,14 @@
 
     activity_tab.expect_journal_mention(text: other_member_user.name)
 
-    wp_page.click_custom_action("Close")
+    wp_page.click_automation("Close")
     wp_page.expect_attributes status: closed_status.name,
                               priority: immediate_priority.name
 
-    wp_page.expect_custom_action("Reset")
-    wp_page.expect_no_custom_action("Close")
+    wp_page.expect_automation("Reset")
+    wp_page.expect_no_automation("Close")
 
-    wp_page.click_custom_action("Reset")
+    wp_page.click_automation("Reset")
 
     wp_page.expect_attributes priority: default_priority.name,
                               status: default_status.name,
@@ -375,7 +381,7 @@
     index_ca_page.expect_current_path
     index_ca_page.expect_listed("Unassign", "Close", "Escalate", "Reject")
 
-    reset = CustomAction.find_by(name: "Reject")
+    reset = Automation.find_by(name: "Reject")
     expect(reset.actions.length).to eq(3)
     expect(reset.conditions.length).to eq(1)
 
@@ -389,21 +395,21 @@
 
     wp_page.visit!
 
-    wp_page.expect_custom_action("Unassign")
-    wp_page.expect_custom_action("Close")
-    wp_page.expect_custom_action("Escalate")
-    wp_page.expect_custom_action("Move project")
-    wp_page.expect_custom_action("Reject")
-    wp_page.expect_no_custom_action("Reset")
-    wp_page.expect_custom_action_order("Move project", "Close", "Reject", "Unassign", "Escalate")
+    wp_page.expect_automation("Unassign")
+    wp_page.expect_automation("Close")
+    wp_page.expect_automation("Escalate")
+    wp_page.expect_automation("Move project")
+    wp_page.expect_automation("Reject")
+    wp_page.expect_no_automation("Reset")
+    wp_page.expect_automation_order("Move project", "Close", "Reject", "Unassign", "Escalate")
 
-    wp_page.click_custom_action("Reject")
+    wp_page.click_automation("Reject")
     wp_page.expect_attributes assignee: "-",
                               status: rejected_status.name,
                               priority: default_priority.name
 
-    wp_page.expect_custom_action("Close")
-    wp_page.expect_no_custom_action("Reject")
+    wp_page.expect_automation("Close")
+    wp_page.expect_no_automation("Reject")
 
     # Delete 'Reject' from list of actions
     login_as(admin)
@@ -419,25 +425,25 @@
 
     wp_page.visit!
 
-    wp_page.expect_no_custom_action("Unassign")
-    wp_page.expect_custom_action("Close")
-    wp_page.expect_custom_action("Escalate")
-    wp_page.expect_no_custom_action("Reject")
+    wp_page.expect_no_automation("Unassign")
+    wp_page.expect_automation("Close")
+    wp_page.expect_automation("Escalate")
+    wp_page.expect_no_automation("Reject")
 
     # Move project
-    wp_page.click_custom_action("Move project")
+    wp_page.click_automation("Move project")
 
     wp_page.expect_attributes assignee: "-",
                               status: rejected_status.name,
                               type: other_type.name.upcase,
-                              "customField#{date_custom_field.id}" => (Date.today + 5.days).strftime("%m/%d/%Y")
+                              "customField#{date_custom_field.id}" => (Time.zone.today + 5.days).strftime("%m/%d/%Y")
     expect(page)
-      .to have_content(I18n.t("js.project.click_to_switch_to_project", projectname: other_project.name))
+      .to have_text(I18n.t("js.project.click_to_switch_to_project", projectname: other_project.name))
 
     ## Bump the lockVersion and by that force a conflict.
     work_package.reload.touch
 
-    wp_page.click_custom_action("Escalate", expect_success: false)
+    wp_page.click_automation("Escalate", expect_success: false)
 
     wp_page.expect_conflict_error_banner
   end
@@ -449,6 +455,7 @@
     new_ca_page = index_ca_page.new
 
     new_ca_page.set_name("Current date")
+    new_ca_page.set_button_label("Current date")
     new_ca_page.set_description("Sets the current date")
     new_ca_page.add_action("Date", "Current date")
 
@@ -457,12 +464,12 @@
     index_ca_page.expect_current_path
     index_ca_page.expect_listed("Current date")
 
-    date_action = CustomAction.last
+    date_action = Automation.last
     expect(date_action.actions.length).to eq(1)
     expect(date_action.conditions.length).to eq(0)
 
     index_ca_page.edit("Current date")
-    expect(page).to have_select("custom_action_actions_date", selected: "Current date")
+    expect(page).to have_select("automation_actions_date", selected: "Current date")
   end
 
   it "editing a status custom action (Regression #61888)" do
@@ -472,6 +479,7 @@
     new_ca_page = index_ca_page.new
 
     new_ca_page.set_name("Status")
+    new_ca_page.set_button_label("Status")
     new_ca_page.set_description("Sets some status")
     new_ca_page.add_action("Status", "Close")
 
@@ -480,12 +488,12 @@
     index_ca_page.expect_current_path
     index_ca_page.expect_listed("Status")
 
-    date_action = CustomAction.last
+    date_action = Automation.last
     expect(date_action.actions.length).to eq(1)
     expect(date_action.actions.first.value_objects).to contain_exactly(label: "Closed", value: closed_status.id)
 
     edit_page = index_ca_page.edit("Status")
-    page.within "#custom-actions-form--actions" do
+    page.within "#automations-form--actions" do
       edit_page.expect_selected_option "Close"
     end
   end
@@ -496,6 +504,7 @@
 
     new_ca_page = index_ca_page.new
     new_ca_page.set_name("Unassign")
+    new_ca_page.set_button_label("Unassign")
     new_ca_page.set_description("Removes the assignee")
     new_ca_page.add_action("Assignee", "-")
     new_ca_page.expect_action("assigned_to", nil)
@@ -505,7 +514,7 @@
     index_ca_page.expect_current_path
     index_ca_page.expect_listed("Unassign")
 
-    unassign = CustomAction.last
+    unassign = Automation.last
     expect(unassign.actions.length).to eq(1)
     expect(unassign.conditions.length).to eq(0)
 
@@ -515,13 +524,13 @@
 
     wp_page.ensure_page_loaded
     wait_for_network_idle
-    wp_page.expect_custom_action("Unassign")
+    wp_page.expect_automation("Unassign")
 
     # Stop sending ajax requests in order to test disabled fields upon submit
     wp_page.disable_ajax_requests
 
-    wp_page.click_custom_action("Unassign", expect_success: false)
-    wp_page.expect_custom_action_disabled("Unassign")
+    wp_page.click_automation("Unassign", expect_success: false)
+    wp_page.expect_automation_disabled("Unassign")
     find('[data-field-name="estimatedTime"]').click
     expect(page).to have_css("#wp-#{work_package.id}-inline-edit--field-estimatedTime[disabled]")
   end
@@ -537,8 +546,8 @@
     end
 
     before do
-      create(:custom_action,
-             actions: [CustomActions::Actions::AssignedTo.new(value: nil)],
+      create(:automation,
+             actions: [Automations::Actions::AssignedTo.new(value: nil)],
              name: "Unassign")
     end
 
@@ -549,7 +558,7 @@
 
       wp_page.ensure_page_loaded
 
-      wp_page.click_custom_action("Unassign", expect_success: true)
+      wp_page.click_automation("Unassign", expect_success: true)
     end
   end
 
@@ -559,6 +568,7 @@
 
       new_ca_page = index_ca_page.new
       new_ca_page.set_name("MultiUser")
+      new_ca_page.set_button_label("MultiUser")
       new_ca_page.set_description("Multiple User Custom Field Test")
       new_ca_page.add_action(multi_user_custom_field.name, other_member_user.name)
       new_ca_page.expect_action(multi_user_custom_field.name, [other_member_user.name])
@@ -576,8 +586,8 @@
   context "when staying on the page for multiple changes (Bug#OP-19472)",
           with_settings: { work_packages_identifier: "semantic" } do
     let!(:unassign_ca) do
-      create(:custom_action,
-             actions: [CustomActions::Actions::AssignedTo.new(nil)],
+      create(:automation,
+             actions: [Automations::Actions::AssignedTo.new(nil)],
              name: "Unassign")
     end
 
@@ -586,8 +596,8 @@
              principal: admin,
              project: project,
              roles: [role])
-      create(:custom_action,
-             actions: [CustomActions::Actions::Responsible.new("current_user")],
+      create(:automation,
+             actions: [Automations::Actions::Responsible.new("current_user")],
              name: "Be responsible")
     end
 
@@ -602,9 +612,9 @@
     it "works when clicking two buttons" do
       wp_page.visit!
 
-      wp_page.click_custom_action(unassign_ca.name, expect_success: true)
+      wp_page.click_automation(unassign_ca.name, expect_success: true)
 
-      wp_page.click_custom_action(responsible_ca.name, expect_success: true)
+      wp_page.click_automation(responsible_ca.name, expect_success: true)
 
       wp_page.expect_attributes(
         assignee: "-",
diff --git a/spec/helpers/no_results_helper_spec.rb b/spec/helpers/no_results_helper_spec.rb
index 4fabb3c60ead..e743d2f746e1 100644
--- a/spec/helpers/no_results_helper_spec.rb
+++ b/spec/helpers/no_results_helper_spec.rb
@@ -50,14 +50,13 @@
       expect(no_results_box).to have_link "Add some foo", href: "/"
     end
 
-    it "contains title and content_link with custom text" do
+    it "contains title with custom text" do
       no_results_box = helper.no_results_box(action_url: root_path,
                                              display_action: true,
-                                             custom_title: "This is a different title about foo",
-                                             custom_action_text: "Link to nowhere")
+                                             custom_title: "This is a different title about foo")
 
       expect(no_results_box).to have_content "This is a different title about foo"
-      expect(no_results_box).to have_link "Link to nowhere", href: "/"
+      expect(no_results_box).to have_link "Add some foo", href: "/"
     end
   end
 end
diff --git a/spec/lib/api/v3/custom_actions/custom_action_representer_generation_spec.rb b/spec/lib/api/v3/custom_actions/custom_action_representer_generation_spec.rb
index af9baad6cb9c..7e35d9ae6bfe 100644
--- a/spec/lib/api/v3/custom_actions/custom_action_representer_generation_spec.rb
+++ b/spec/lib/api/v3/custom_actions/custom_action_representer_generation_spec.rb
@@ -33,11 +33,11 @@
 RSpec.describe API::V3::CustomActions::CustomActionRepresenter do
   include API::V3::Utilities::PathHelper
 
-  let(:custom_action) { build_stubbed(:custom_action) }
+  let(:automation) { build_stubbed(:automation) }
   let(:user) { build_stubbed(:user) }
 
   let(:representer) do
-    described_class.new(custom_action, current_user: user, embed_links: true)
+    described_class.new(automation, current_user: user, embed_links: true)
   end
 
   subject { representer.to_json }
@@ -51,13 +51,13 @@
 
     it "has a name property" do
       expect(subject)
-        .to be_json_eql(custom_action.name.to_json)
+        .to be_json_eql(automation.name.to_json)
         .at_path("name")
     end
 
     it "has a description property" do
       expect(subject)
-        .to be_json_eql(custom_action.description.to_json)
+        .to be_json_eql(automation.description.to_json)
         .at_path("description")
     end
   end
@@ -65,14 +65,14 @@
   context "links" do
     it_behaves_like "has a titled link" do
       let(:link) { "self" }
-      let(:href) { api_v3_paths.custom_action(custom_action.id) }
-      let(:title) { custom_action.name }
+      let(:href) { api_v3_paths.custom_action(automation.id) }
+      let(:title) { automation.name }
     end
 
     it_behaves_like "has a titled link" do
       let(:link) { "executeImmediately" }
-      let(:href) { api_v3_paths.custom_action_execute(custom_action.id) }
-      let(:title) { "Execute #{custom_action.name}" }
+      let(:href) { api_v3_paths.custom_action_execute(automation.id) }
+      let(:title) { "Execute #{automation.name}" }
       let(:method) { "post" }
     end
   end
diff --git a/spec/lib/api/v3/work_packages/eager_loading/custom_actions_integration_spec.rb b/spec/lib/api/v3/work_packages/eager_loading/automation_integration_spec.rb
similarity index 69%
rename from spec/lib/api/v3/work_packages/eager_loading/custom_actions_integration_spec.rb
rename to spec/lib/api/v3/work_packages/eager_loading/automation_integration_spec.rb
index c734e757a293..bdc41a4a47de 100644
--- a/spec/lib/api/v3/work_packages/eager_loading/custom_actions_integration_spec.rb
+++ b/spec/lib/api/v3/work_packages/eager_loading/automation_integration_spec.rb
@@ -31,7 +31,7 @@
 require "spec_helper"
 require_relative "eager_loading_mock_wrapper"
 
-RSpec.describe API::V3::WorkPackages::EagerLoading::CustomAction do
+RSpec.describe API::V3::WorkPackages::EagerLoading::Automation do
   let!(:work_package1) { create(:work_package) }
   let!(:work_package2) { create(:work_package) }
   let!(:user) do
@@ -39,13 +39,13 @@
            member_with_roles: { work_package2.project => role })
   end
   let!(:role) { create(:project_role) }
-  let!(:status_custom_action) do
-    create(:custom_action,
-           conditions: [CustomActions::Conditions::Status.new(work_package1.status_id.to_s)])
+  let!(:status_automation) do
+    create(:automation,
+           conditions: [Automations::Conditions::Status.new(work_package1.status_id.to_s)])
   end
-  let!(:role_custom_action) do
-    create(:custom_action,
-           conditions: [CustomActions::Conditions::Role.new(role.id)])
+  let!(:role_automation) do
+    create(:automation,
+           conditions: [Automations::Conditions::Role.new(role.id)])
   end
 
   before do
@@ -53,19 +53,21 @@
   end
 
   describe ".apply" do
-    it "preloads the correct custom_actions" do
+    it "preloads the correct automations" do
       wrapped = EagerLoadingMockWrapper.wrap(described_class, [work_package1, work_package2])
 
+      # rubocop:disable RSpec/MessageSpies
       expect(work_package1)
-        .not_to receive(:custom_actions)
+        .not_to receive(:automations)
       expect(work_package2)
-        .not_to receive(:custom_actions)
+        .not_to receive(:automations)
+      # rubocop:enable RSpec/MessageSpies
 
-      expect(wrapped.detect { |w| w.id == work_package1.id }.custom_actions(user))
-        .to contain_exactly(status_custom_action)
+      expect(wrapped.detect { |w| w.id == work_package1.id }.automations(user))
+        .to contain_exactly(status_automation)
 
-      expect(wrapped.detect { |w| w.id == work_package2.id }.custom_actions(user))
-        .to contain_exactly(role_custom_action)
+      expect(wrapped.detect { |w| w.id == work_package2.id }.automations(user))
+        .to contain_exactly(role_automation)
     end
   end
 end
diff --git a/spec/lib/api/v3/work_packages/work_package_representer_spec.rb b/spec/lib/api/v3/work_packages/work_package_representer_spec.rb
index 32a6f03e78b2..8edcd5a2c3c3 100644
--- a/spec/lib/api/v3/work_packages/work_package_representer_spec.rb
+++ b/spec/lib/api/v3/work_packages/work_package_representer_spec.rb
@@ -1585,11 +1585,11 @@
 
     describe "customActions" do
       it "has a collection of customActions" do
-        unassign_action = build_stubbed(:custom_action,
-                                        actions: [CustomActions::Actions::AssignedTo.new(value: nil)],
+        unassign_action = build_stubbed(:automation,
+                                        actions: [Automations::Actions::AssignedTo.new(value: nil)],
                                         name: "Unassign")
         allow(work_package)
-          .to receive(:custom_actions)
+          .to receive(:automations)
                 .and_return([unassign_action])
 
         expected = [
@@ -1700,11 +1700,11 @@
 
     describe "customActions" do
       it "has an array of customActions" do
-        unassign_action = build_stubbed(:custom_action,
-                                        actions: [CustomActions::Actions::AssignedTo.new(value: nil)],
+        unassign_action = build_stubbed(:automation,
+                                        actions: [Automations::Actions::AssignedTo.new(value: nil)],
                                         name: "Unassign")
         allow(work_package)
-          .to receive(:custom_actions)
+          .to receive(:automations)
                 .and_return([unassign_action])
 
         expect(subject)
diff --git a/spec/models/custom_action_spec.rb b/spec/models/automation_spec.rb
similarity index 76%
rename from spec/models/custom_action_spec.rb
rename to spec/models/automation_spec.rb
index de2e5fd39c2d..f9946349738f 100644
--- a/spec/models/custom_action_spec.rb
+++ b/spec/models/automation_spec.rb
@@ -30,10 +30,10 @@
 
 require "spec_helper"
 
-RSpec.describe CustomAction do
-  let(:stubbed_instance) { build_stubbed(:custom_action) }
-  let(:instance) { create(:custom_action, name: "zzzzzzzzz") }
-  let(:other_instance) { create(:custom_action, name: "aaaaa") }
+RSpec.describe Automation do
+  let(:stubbed_instance) { build_stubbed(:automation) }
+  let(:instance) { create(:automation, name: "zzzzzzzzz") }
+  let(:other_instance) { create(:automation, name: "aaaaa") }
 
   describe "#name" do
     it "can be set and read" do
@@ -58,21 +58,21 @@
       stubbed_instance.name = "a" * 256
 
       expect(stubbed_instance)
-        .to be_invalid
+        .not_to be_valid
     end
 
     it "is invalid with a nil name" do
       stubbed_instance.name = nil
 
       expect(stubbed_instance)
-        .to be_invalid
+        .not_to be_valid
     end
 
     it "is invalid with an empty name" do
       stubbed_instance.name = ""
 
       expect(stubbed_instance)
-        .to be_invalid
+        .not_to be_valid
     end
   end
 
@@ -95,18 +95,18 @@
     end
 
     it "can be set and read" do
-      stubbed_instance.actions = [CustomActions::Actions::AssignedTo.new(1)]
+      stubbed_instance.actions = [Automations::Actions::AssignedTo.new(1)]
 
       expect(stubbed_instance.actions.map { |a| [a.key, a.values] })
         .to contain_exactly([:assigned_to, [1]])
     end
 
     it "can be persisted" do
-      instance.actions = [CustomActions::Actions::AssignedTo.new(1)]
+      instance.actions = [Automations::Actions::AssignedTo.new(1)]
 
       instance.save!
 
-      expect(CustomAction.find(instance.id).actions.map { |a| [a.key, a.values] })
+      expect(described_class.find(instance.id).actions.map { |a| [a.key, a.values] })
         .to contain_exactly([:assigned_to, [1]])
     end
   end
@@ -118,7 +118,7 @@
     end
 
     it "returns the activated actions with their selected value and all other with the default value" do
-      stubbed_instance.actions = [CustomActions::Actions::AssignedTo.new(1)]
+      stubbed_instance.actions = [Automations::Actions::AssignedTo.new(1)]
 
       expect(stubbed_instance.all_actions.map { |a| [a.key, a.values] })
         .to include([:assigned_to, [1]], [:status, []])
@@ -149,25 +149,25 @@
     end
 
     it "can be set and read" do
-      stubbed_instance.conditions = [CustomActions::Conditions::Status.new(status.id),
-                                     CustomActions::Conditions::Role.new(role.id)]
+      stubbed_instance.conditions = [Automations::Conditions::Status.new(status.id),
+                                     Automations::Conditions::Role.new(role.id)]
 
       expect(stubbed_instance.conditions.map { |a| [a.key, a.values] })
         .to contain_exactly([:status, [status.id]], [:role, [role.id]])
     end
 
     it "can be persisted" do
-      instance.conditions = [CustomActions::Conditions::Status.new(status.id),
-                             CustomActions::Conditions::Role.new(role.id)]
+      instance.conditions = [Automations::Conditions::Status.new(status.id),
+                             Automations::Conditions::Role.new(role.id)]
 
       instance.save!
 
-      expect(CustomAction.find(instance.id).conditions.map { |a| [a.key, a.values] })
+      expect(described_class.find(instance.id).conditions.map { |a| [a.key, a.values] })
         .to contain_exactly([:status, [status.id]], [:role, [role.id]])
     end
 
     it "existing permissions can be removed" do
-      instance.conditions = [CustomActions::Conditions::Project.new(project.id)]
+      instance.conditions = [Automations::Conditions::Project.new(project.id)]
 
       instance.save!
 
@@ -175,17 +175,17 @@
 
       instance.save!
 
-      expect(CustomAction.find(instance.id).conditions.map { |a| [a.key, a.values] })
+      expect(described_class.find(instance.id).conditions.map { |a| [a.key, a.values] })
         .to be_empty
     end
   end
 
   describe "#conditions_fulfilled?" do
-    let(:work_package) { double("work_package") }
-    let(:user) { double("user") }
+    let(:work_package) { instance_double(WorkPackage) }
+    let(:user) { instance_double(User) }
 
     let(:stubbed_condition1) do
-      condition = double("condition1")
+      condition = instance_double(Automations::Conditions::Base)
       allow(condition)
         .to receive(:fulfilled_by?)
         .with(work_package, user)
@@ -193,7 +193,7 @@
       condition
     end
     let(:stubbed_condition2) do
-      condition = double("condition2")
+      condition = instance_double(Automations::Conditions::Base)
       allow(condition)
         .to receive(:fulfilled_by?)
         .with(work_package, user)
@@ -209,19 +209,19 @@
         .and_return [stubbed_condition1, stubbed_condition2]
     end
 
-    context "all conditions fulfilled" do
+    context "with all conditions fulfilled" do
       it "is true" do
-        expect(stubbed_instance.conditions_fulfilled?(work_package, user))
-          .to be_truthy
+        expect(stubbed_instance)
+          .to be_conditions_fulfilled(work_package, user)
       end
     end
 
-    context "but one condition not fulfilled" do
+    context "with one condition not fulfilled" do
       let(:condition1_fulfilled) { false }
 
       it "is false" do
-        expect(stubbed_instance.conditions_fulfilled?(work_package, user))
-          .to be_falsey
+        expect(stubbed_instance)
+          .not_to be_conditions_fulfilled(work_package, user)
       end
     end
   end
diff --git a/spec/models/custom_actions/actions/assigned_to_spec.rb b/spec/models/automations/actions/assigned_to_spec.rb
similarity index 87%
rename from spec/models/custom_actions/actions/assigned_to_spec.rb
rename to spec/models/automations/actions/assigned_to_spec.rb
index 3b6591f2ed35..c4f8bc88bdfa 100644
--- a/spec/models/custom_actions/actions/assigned_to_spec.rb
+++ b/spec/models/automations/actions/assigned_to_spec.rb
@@ -30,15 +30,14 @@
 require "spec_helper"
 require_relative "../shared_expectations"
 
-RSpec.describe CustomActions::Actions::AssignedTo do
+RSpec.describe Automations::Actions::AssignedTo do
   let(:key) { :assigned_to }
   let(:type) { :user }
   let(:allowed_values) do
     users = [build_stubbed(:user),
              build_stubbed(:group)]
-    allow(Principal)
-      .to receive_message_chain(:not_locked, :select, :select_for_name, :ordered_by_name)
-      .and_return(users)
+    allow(Principal).to receive_messages(not_locked: Principal, select: Principal,
+                                         select_for_name: Principal, ordered_by_name: users)
 
     [{ value: nil, label: "-" },
      { value: "current_user", label: "(Assign to executing user)" },
@@ -74,7 +73,7 @@
 
     it "includes the value in available_values" do
       expect(subject.associated)
-        .to include([subject.current_user_value_key, I18n.t("custom_actions.actions.assigned_to.executing_user_value")])
+        .to include([subject.current_user_value_key, I18n.t("automations.actions.assigned_to.executing_user_value")])
     end
 
     context "when logged in" do
@@ -88,7 +87,7 @@
       end
 
       it "validates the me value when executing" do
-        errors = ActiveModel::Errors.new(CustomAction.new)
+        errors = ActiveModel::Errors.new(Automation.new)
         subject.validate errors
         expect(errors.symbols_for(:actions)).to be_empty
       end
@@ -101,7 +100,7 @@
       end
 
       it "validates the me value when executing" do
-        errors = ActiveModel::Errors.new(CustomAction.new)
+        errors = ActiveModel::Errors.new(Automation.new)
         subject.validate errors
         expect(errors.symbols_for(:actions)).to include :not_logged_in
       end
diff --git a/spec/models/custom_actions/actions/custom_field_spec.rb b/spec/models/automations/actions/custom_field_spec.rb
similarity index 98%
rename from spec/models/custom_actions/actions/custom_field_spec.rb
rename to spec/models/automations/actions/custom_field_spec.rb
index f74fbe29884b..07f205da059f 100644
--- a/spec/models/custom_actions/actions/custom_field_spec.rb
+++ b/spec/models/automations/actions/custom_field_spec.rb
@@ -30,7 +30,7 @@
 require "spec_helper"
 require_relative "../shared_expectations"
 
-RSpec.describe CustomActions::Actions::CustomField do
+RSpec.describe Automations::Actions::CustomField do
   let(:scope) { instance_double(ActiveRecord::Relation) }
   let(:list_custom_field) do
     build_stubbed(:list_wp_custom_field,
@@ -101,7 +101,7 @@
   describe ".all" do
     before do
       allow(WorkPackageCustomField)
-        .to receive(:usable_as_custom_action)
+        .to receive(:usable_as_automation)
         .and_return(custom_fields)
     end
 
@@ -282,7 +282,7 @@
 
         it "includes the value in available_values" do
           expect(instance.associated)
-            .to include([instance.current_user_value_key, I18n.t("custom_actions.actions.assigned_to.executing_user_value")])
+            .to include([instance.current_user_value_key, I18n.t("automations.actions.assigned_to.executing_user_value")])
         end
 
         context "when logged in" do
@@ -296,7 +296,7 @@
           end
 
           it "validates the me value when executing" do
-            errors = ActiveModel::Errors.new(CustomAction.new)
+            errors = ActiveModel::Errors.new(Automation.new)
             instance.validate errors
             expect(errors.symbols_for(:actions)).to be_empty
           end
@@ -313,7 +313,7 @@
           end
 
           it "validates the me value when executing" do
-            errors = ActiveModel::Errors.new(CustomAction.new)
+            errors = ActiveModel::Errors.new(Automation.new)
             instance.validate errors
             expect(errors.symbols_for(:actions)).to include :not_logged_in
           end
diff --git a/spec/models/custom_actions/actions/date_spec.rb b/spec/models/automations/actions/date_spec.rb
similarity index 88%
rename from spec/models/custom_actions/actions/date_spec.rb
rename to spec/models/automations/actions/date_spec.rb
index 1c3d2fce08e6..d91ccc2b2f07 100644
--- a/spec/models/custom_actions/actions/date_spec.rb
+++ b/spec/models/automations/actions/date_spec.rb
@@ -31,24 +31,24 @@
 require "spec_helper"
 require_relative "../shared_expectations"
 
-RSpec.describe CustomActions::Actions::Date do
+RSpec.describe Automations::Actions::Date do
   let(:key) { :date }
   let(:type) { :date_property }
-  let(:value) { Date.today }
+  let(:value) { Time.zone.today }
 
   it_behaves_like "base custom action" do
     describe "#apply" do
       let(:work_package) { build_stubbed(:work_package) }
 
       it "sets both start and finish date to the action's value" do
-        instance.values = [Date.today + 5]
+        instance.values = [Time.zone.today + 5]
 
         instance.apply(work_package)
 
         expect(work_package.start_date)
-          .to eql Date.today + 5
+          .to eql Time.zone.today + 5
         expect(work_package.due_date)
-          .to eql Date.today + 5
+          .to eql Time.zone.today + 5
       end
 
       it "sets both start and finish date to the current date if so specified" do
@@ -57,9 +57,9 @@
         instance.apply(work_package)
 
         expect(work_package.start_date)
-          .to eql Date.today
+          .to eql Time.zone.today
         expect(work_package.due_date)
-          .to eql Date.today
+          .to eql Time.zone.today
       end
     end
 
diff --git a/spec/models/custom_actions/actions/done_ratio_spec.rb b/spec/models/automations/actions/done_ratio_spec.rb
similarity index 96%
rename from spec/models/custom_actions/actions/done_ratio_spec.rb
rename to spec/models/automations/actions/done_ratio_spec.rb
index 92970bcca527..5c54d6463234 100644
--- a/spec/models/custom_actions/actions/done_ratio_spec.rb
+++ b/spec/models/automations/actions/done_ratio_spec.rb
@@ -31,7 +31,7 @@
 require "spec_helper"
 require_relative "../shared_expectations"
 
-RSpec.describe CustomActions::Actions::DoneRatio do
+RSpec.describe Automations::Actions::DoneRatio do
   let(:key) { :done_ratio }
   let(:type) { :integer_property }
 
@@ -58,7 +58,7 @@
 
     describe "validate" do
       let(:errors) do
-        build_stubbed(:custom_action).errors
+        build_stubbed(:automation).errors
       end
 
       it "is valid for values between 0 and 100" do
diff --git a/spec/models/custom_actions/actions/due_date_spec.rb b/spec/models/automations/actions/due_date_spec.rb
similarity index 95%
rename from spec/models/custom_actions/actions/due_date_spec.rb
rename to spec/models/automations/actions/due_date_spec.rb
index 7dccff52c776..ae909021080a 100644
--- a/spec/models/custom_actions/actions/due_date_spec.rb
+++ b/spec/models/automations/actions/due_date_spec.rb
@@ -31,10 +31,10 @@
 require "spec_helper"
 require_relative "../shared_expectations"
 
-RSpec.describe CustomActions::Actions::DueDate do
+RSpec.describe Automations::Actions::DueDate do
   let(:key) { :due_date }
   let(:type) { :date_property }
-  let(:value) { Date.today }
+  let(:value) { Time.zone.today }
 
   it_behaves_like "base custom action" do
     describe "#multi_value?" do
diff --git a/spec/models/custom_actions/actions/estimated_hours_spec.rb b/spec/models/automations/actions/estimated_hours_spec.rb
similarity index 95%
rename from spec/models/custom_actions/actions/estimated_hours_spec.rb
rename to spec/models/automations/actions/estimated_hours_spec.rb
index e2a5fe3a50db..cc5bdd0ee0f5 100644
--- a/spec/models/custom_actions/actions/estimated_hours_spec.rb
+++ b/spec/models/automations/actions/estimated_hours_spec.rb
@@ -31,7 +31,7 @@
 require "spec_helper"
 require_relative "../shared_expectations"
 
-RSpec.describe CustomActions::Actions::EstimatedHours do
+RSpec.describe Automations::Actions::EstimatedHours do
   let(:key) { :estimated_hours }
   let(:type) { :float_property }
   let(:value) { 1.0 }
@@ -59,7 +59,7 @@
 
     describe "validate" do
       let(:errors) do
-        build_stubbed(:custom_action).errors
+        build_stubbed(:automation).errors
       end
 
       it "is valid for values equal to or greater than 0" do
diff --git a/spec/models/custom_actions/actions/notify_spec.rb b/spec/models/automations/actions/notify_spec.rb
similarity index 81%
rename from spec/models/custom_actions/actions/notify_spec.rb
rename to spec/models/automations/actions/notify_spec.rb
index 00fa45e52232..e8ac98031aa1 100644
--- a/spec/models/custom_actions/actions/notify_spec.rb
+++ b/spec/models/automations/actions/notify_spec.rb
@@ -30,16 +30,15 @@
 require "spec_helper"
 require_relative "../shared_expectations"
 
-RSpec.describe CustomActions::Actions::Notify do
+RSpec.describe Automations::Actions::Notify do
   let(:key) { :notify }
   let(:type) { :associated_property }
   let(:allowed_values) do
     users = [build_stubbed(:user),
              build_stubbed(:group)]
 
-    allow(Principal)
-      .to receive_message_chain(:not_locked, :select, :select_for_name, :ordered_by_name)
-            .and_return(users)
+    allow(Principal).to receive_messages(not_locked: Principal, select: Principal,
+                                         select_for_name: Principal, ordered_by_name: users)
 
     [{ value: nil, label: "-" },
      { value: users.first.id, label: users.first.name },
@@ -66,17 +65,19 @@
                       build_stubbed(:group),
                       build_stubbed(:user)]
 
-        allow(Principal)
-          .to receive_message_chain(:not_locked, :select, :select_for_name, :ordered_by_name, :where)
-          .and_return(principals)
+        allow(Principal).to receive_messages(not_locked: Principal, select: Principal,
+                                             select_for_name: Principal, ordered_by_name: Principal,
+                                             where: principals)
 
         instance.values = principals.map(&:id)
 
-        expect(work_package)
-          .to receive(:journal_notes=)
-          .with("user##{principals[0].id}, group##{principals[1].id}, user##{principals[2].id}")
+        allow(work_package).to receive(:journal_notes=)
 
         instance.apply(work_package)
+
+        expect(work_package)
+          .to have_received(:journal_notes=)
+          .with("user##{principals[0].id}, group##{principals[1].id}, user##{principals[2].id}")
       end
     end
 
diff --git a/spec/models/custom_actions/actions/priority_spec.rb b/spec/models/automations/actions/priority_spec.rb
similarity index 92%
rename from spec/models/custom_actions/actions/priority_spec.rb
rename to spec/models/automations/actions/priority_spec.rb
index 331339555be1..b6ac021d508a 100644
--- a/spec/models/custom_actions/actions/priority_spec.rb
+++ b/spec/models/automations/actions/priority_spec.rb
@@ -30,15 +30,13 @@
 require "spec_helper"
 require_relative "../shared_expectations"
 
-RSpec.describe CustomActions::Actions::Priority do
+RSpec.describe Automations::Actions::Priority do
   let(:key) { :priority }
   let(:type) { :associated_property }
   let(:allowed_values) do
     priorities = [build_stubbed(:issue_priority),
                   build_stubbed(:issue_priority)]
-    allow(IssuePriority)
-      .to receive_message_chain(:select, :order)
-            .and_return(priorities)
+    allow(IssuePriority).to receive_messages(select: IssuePriority, order: priorities)
 
     [{ value: priorities.first.id, label: priorities.first.name },
      { value: priorities.last.id, label: priorities.last.name }]
diff --git a/spec/models/custom_actions/actions/project_spec.rb b/spec/models/automations/actions/project_spec.rb
similarity index 92%
rename from spec/models/custom_actions/actions/project_spec.rb
rename to spec/models/automations/actions/project_spec.rb
index 1296f0973474..3b30d745d543 100644
--- a/spec/models/custom_actions/actions/project_spec.rb
+++ b/spec/models/automations/actions/project_spec.rb
@@ -30,7 +30,7 @@
 require "spec_helper"
 require_relative "../shared_expectations"
 
-RSpec.describe CustomActions::Actions::Project do
+RSpec.describe Automations::Actions::Project do
   let(:key) { :project }
   let(:type) { :project }
   let(:priority) { 10 }
@@ -38,9 +38,7 @@
   let(:allowed_values) do
     projects = [build_stubbed(:project),
                 build_stubbed(:project)]
-    allow(Project)
-      .to receive_message_chain(:select, :order)
-            .and_return(projects)
+    allow(Project).to receive_messages(select: Project, order: projects)
 
     [{ value: projects.first.id, label: projects.first.name },
      { value: projects.last.id, label: projects.last.name }]
diff --git a/spec/models/custom_actions/actions/responsible_spec.rb b/spec/models/automations/actions/responsible_spec.rb
similarity index 87%
rename from spec/models/custom_actions/actions/responsible_spec.rb
rename to spec/models/automations/actions/responsible_spec.rb
index 3321f569c205..fc135b0801e6 100644
--- a/spec/models/custom_actions/actions/responsible_spec.rb
+++ b/spec/models/automations/actions/responsible_spec.rb
@@ -30,16 +30,15 @@
 require "spec_helper"
 require_relative "../shared_expectations"
 
-RSpec.describe CustomActions::Actions::Responsible do
+RSpec.describe Automations::Actions::Responsible do
   let(:key) { :responsible }
   let(:type) { :user }
   let(:allowed_values) do
     principals = [build_stubbed(:user),
                   build_stubbed(:group)]
 
-    allow(User)
-      .to receive_message_chain(:not_locked, :select, :select_for_name, :ordered_by_name)
-            .and_return(principals)
+    allow(User).to receive_messages(not_locked: User, select: User,
+                                    select_for_name: User, ordered_by_name: principals)
 
     [{ value: nil, label: "-" },
      { value: "current_user", label: "(Assign to executing user)" },
@@ -75,7 +74,7 @@
 
     it "includes the value in available_values" do
       expect(subject.associated)
-        .to include([subject.current_user_value_key, I18n.t("custom_actions.actions.assigned_to.executing_user_value")])
+        .to include([subject.current_user_value_key, I18n.t("automations.actions.assigned_to.executing_user_value")])
     end
 
     context "when logged in" do
@@ -89,7 +88,7 @@
       end
 
       it "validates the me value when executing" do
-        errors = ActiveModel::Errors.new(CustomAction.new)
+        errors = ActiveModel::Errors.new(Automation.new)
         subject.validate errors
         expect(errors.symbols_for(:actions)).to be_empty
       end
@@ -102,7 +101,7 @@
       end
 
       it "validates the me value when executing" do
-        errors = ActiveModel::Errors.new(CustomAction.new)
+        errors = ActiveModel::Errors.new(Automation.new)
         subject.validate errors
         expect(errors.symbols_for(:actions)).to include :not_logged_in
       end
diff --git a/spec/models/custom_actions/actions/start_date_spec.rb b/spec/models/automations/actions/start_date_spec.rb
similarity index 95%
rename from spec/models/custom_actions/actions/start_date_spec.rb
rename to spec/models/automations/actions/start_date_spec.rb
index 6e01824aff45..e8dbc35485ef 100644
--- a/spec/models/custom_actions/actions/start_date_spec.rb
+++ b/spec/models/automations/actions/start_date_spec.rb
@@ -31,10 +31,10 @@
 require "spec_helper"
 require_relative "../shared_expectations"
 
-RSpec.describe CustomActions::Actions::StartDate do
+RSpec.describe Automations::Actions::StartDate do
   let(:key) { :start_date }
   let(:type) { :date_property }
-  let(:value) { Date.today }
+  let(:value) { Time.zone.today }
 
   it_behaves_like "base custom action" do
     describe "#multi_value?" do
diff --git a/spec/models/custom_actions/actions/status_spec.rb b/spec/models/automations/actions/status_spec.rb
similarity index 92%
rename from spec/models/custom_actions/actions/status_spec.rb
rename to spec/models/automations/actions/status_spec.rb
index c3ffb1cde5b0..69a89542cc4f 100644
--- a/spec/models/custom_actions/actions/status_spec.rb
+++ b/spec/models/automations/actions/status_spec.rb
@@ -30,15 +30,13 @@
 require "spec_helper"
 require_relative "../shared_expectations"
 
-RSpec.describe CustomActions::Actions::Status do
+RSpec.describe Automations::Actions::Status do
   let(:key) { :status }
   let(:type) { :associated_property }
   let(:allowed_values) do
     statuses = [build_stubbed(:status),
                 build_stubbed(:status)]
-    allow(Status)
-      .to receive_message_chain(:select, :order)
-            .and_return(statuses)
+    allow(Status).to receive_messages(select: Status, order: statuses)
 
     [{ value: statuses.first.id, label: statuses.first.name },
      { value: statuses.last.id, label: statuses.last.name }]
diff --git a/spec/models/custom_actions/actions/strategies/user_custom_field_spec.rb b/spec/models/automations/actions/strategies/user_custom_field_spec.rb
similarity index 88%
rename from spec/models/custom_actions/actions/strategies/user_custom_field_spec.rb
rename to spec/models/automations/actions/strategies/user_custom_field_spec.rb
index 21d98dcddbde..eceae4867ba4 100644
--- a/spec/models/custom_actions/actions/strategies/user_custom_field_spec.rb
+++ b/spec/models/automations/actions/strategies/user_custom_field_spec.rb
@@ -5,7 +5,7 @@
 
 require "spec_helper"
 
-module CustomActions
+module Automations
   module Actions
     module Strategies
       RSpec.describe UserCustomField do
@@ -31,13 +31,13 @@ module Strategies
           end
         end
 
-        let(:user_cf_action) { CustomActions::Actions::CustomField.for("custom_field_#{user_cf.id}").new }
-        let(:multi_user_cf_action) { CustomActions::Actions::CustomField.for("custom_field_#{multi_user_cf.id}").new }
+        let(:user_cf_action) { Automations::Actions::CustomField.for("custom_field_#{user_cf.id}").new }
+        let(:multi_user_cf_action) { Automations::Actions::CustomField.for("custom_field_#{multi_user_cf.id}").new }
         let(:single_user_work_package) { create(:work_package, project: single_user_project) }
         let(:multi_user_work_package) { create(:work_package, project: multi_user_project) }
 
-        let(:custom_action) do
-          create(:custom_action,
+        let(:automation) do
+          create(:automation,
                  type_conditions: [single_user_work_package.type],
                  project_conditions: [single_user_project],
                  actions: [user_cf_action, multi_user_cf_action])
@@ -49,12 +49,12 @@ module Strategies
           before do
             user_cf_action.values = users[4].id
             multi_user_cf_action.values = users[1..3].map(&:id)
-            custom_action.save
+            automation.save
           end
 
           it "fails with an error" do
             login_as user
-            result = UpdateWorkPackageService.new(user:, action: custom_action)
+            result = UpdateWorkPackageService.new(user:, action: automation)
                                              .call(work_package: single_user_work_package)
 
             expect(result).to be_failure
@@ -70,29 +70,29 @@ module Strategies
           before do
             user_cf_action.values = user.id
             multi_user_cf_action.values = users[0..3].map(&:id)
-            custom_action.save
+            automation.save
             login_as user
           end
 
           it "succeeds" do
-            result = UpdateWorkPackageService.new(user:, action: custom_action).call(work_package: single_user_work_package)
+            result = UpdateWorkPackageService.new(user:, action: automation).call(work_package: single_user_work_package)
             expect(result).to be_success
 
-            multi_user_result = UpdateWorkPackageService.new(user:, action: custom_action)
+            multi_user_result = UpdateWorkPackageService.new(user:, action: automation)
                                                         .call(work_package: multi_user_work_package)
 
             expect(multi_user_result).to be_success
           end
 
           it "saves the custom field values on the work package" do
-            result = UpdateWorkPackageService.new(user:, action: custom_action)
+            result = UpdateWorkPackageService.new(user:, action: automation)
                                              .call(work_package: single_user_work_package)
 
             updated = result.result.reload
             expect(updated.send("custom_field_#{user_cf.id}")).to eq(user)
             expect(updated.send("custom_field_#{multi_user_cf.id}")).to eq([user])
 
-            muti_user_result = UpdateWorkPackageService.new(user:, action: custom_action)
+            muti_user_result = UpdateWorkPackageService.new(user:, action: automation)
                                              .call(work_package: multi_user_work_package)
 
             updated = muti_user_result.result.reload
@@ -105,12 +105,12 @@ module Strategies
           before do
             user_cf_action.values = "current_user"
             multi_user_cf_action.values = ["current_user"] + users[1..3].map(&:id)
-            custom_action.save
+            automation.save
             login_as user
           end
 
           it "assigns the current user to the custom field" do
-            result = UpdateWorkPackageService.new(user:, action: custom_action)
+            result = UpdateWorkPackageService.new(user:, action: automation)
                                              .call(work_package: single_user_work_package)
 
             updated = result.result.reload
diff --git a/spec/models/custom_actions/actions/type_spec.rb b/spec/models/automations/actions/type_spec.rb
similarity index 97%
rename from spec/models/custom_actions/actions/type_spec.rb
rename to spec/models/automations/actions/type_spec.rb
index 45591d8a3bc4..f4b01eefc9b8 100644
--- a/spec/models/custom_actions/actions/type_spec.rb
+++ b/spec/models/automations/actions/type_spec.rb
@@ -30,7 +30,7 @@
 require "spec_helper"
 require_relative "../shared_expectations"
 
-RSpec.describe CustomActions::Actions::Type do
+RSpec.describe Automations::Actions::Type do
   let(:key) { :type }
   let(:priority) { 20 }
   let(:type) { :associated_property }
diff --git a/spec/models/custom_actions/conditions/project_spec.rb b/spec/models/automations/conditions/project_spec.rb
similarity index 79%
rename from spec/models/custom_actions/conditions/project_spec.rb
rename to spec/models/automations/conditions/project_spec.rb
index 81dd706b9d7e..ea8d61b70610 100644
--- a/spec/models/custom_actions/conditions/project_spec.rb
+++ b/spec/models/automations/conditions/project_spec.rb
@@ -30,7 +30,7 @@
 require "spec_helper"
 require_relative "../shared_expectations"
 
-RSpec.describe CustomActions::Conditions::Project do
+RSpec.describe Automations::Conditions::Project do
   it_behaves_like "associated custom condition" do
     let(:key) { :project }
 
@@ -38,9 +38,7 @@
       it "is the list of all projects" do
         projects = [build_stubbed(:project),
                     build_stubbed(:project)]
-        allow(Project)
-          .to receive_message_chain(:active, :select, :order)
-          .and_return(projects)
+        allow(Project).to receive_messages(active: Project, select: Project, order: projects)
 
         expect(instance.allowed_values)
           .to eql([{ value: projects.first.id, label: projects.first.name },
@@ -49,28 +47,28 @@
     end
 
     describe "#fulfilled_by?" do
-      let(:work_package) { double("work_package", project_id: 1) }
-      let(:user) { double("not relevant") }
+      let(:work_package) { instance_double(WorkPackage, project_id: 1) }
+      let(:user) { instance_double(User) }
 
       it "is true if values are empty" do
         instance.values = []
 
-        expect(instance.fulfilled_by?(work_package, user))
-          .to be_truthy
+        expect(instance)
+          .to be_fulfilled_by(work_package, user)
       end
 
       it "is true if values include work package's project_id" do
         instance.values = [1]
 
-        expect(instance.fulfilled_by?(work_package, user))
-          .to be_truthy
+        expect(instance)
+          .to be_fulfilled_by(work_package, user)
       end
 
       it "is false if values do not include work package's project_id" do
         instance.values = [5]
 
-        expect(instance.fulfilled_by?(work_package, user))
-          .to be_falsey
+        expect(instance)
+          .not_to be_fulfilled_by(work_package, user)
       end
     end
   end
diff --git a/spec/models/custom_actions/conditions/role_spec.rb b/spec/models/automations/conditions/role_spec.rb
similarity index 77%
rename from spec/models/custom_actions/conditions/role_spec.rb
rename to spec/models/automations/conditions/role_spec.rb
index 51d52eced8b3..1f7f2197e871 100644
--- a/spec/models/custom_actions/conditions/role_spec.rb
+++ b/spec/models/automations/conditions/role_spec.rb
@@ -30,7 +30,7 @@
 require "spec_helper"
 require_relative "../shared_expectations"
 
-RSpec.describe CustomActions::Conditions::Role do
+RSpec.describe Automations::Conditions::Role do
   it_behaves_like "associated custom condition" do
     let(:key) { :role }
 
@@ -39,9 +39,7 @@
         roles = [build_stubbed(:project_role),
                  build_stubbed(:project_role)]
 
-        allow(Role)
-          .to receive_message_chain(:givable, :select)
-          .and_return(roles)
+        allow(Role).to receive_messages(givable: Role, select: roles)
 
         expect(instance.allowed_values)
           .to eql([{ value: roles.first.id, label: roles.first.name },
@@ -50,39 +48,39 @@
     end
 
     describe "#fulfilled_by?" do
-      let(:project) { double("project", id: 1) }
-      let(:work_package) { double("work_package", project:, project_id: 1) }
+      let(:project) { instance_double(Project, id: 1) }
+      let(:work_package) { instance_double(WorkPackage, project:, project_id: 1) }
       let(:user) do
-        double("user", id: 3).tap do |user|
+        instance_double(User, id: 3).tap do |user|
           allow(user)
             .to receive(:roles_for_project)
             .with(project)
             .and_return(roles)
         end
       end
-      let(:role1) { double("role", id: 1) }
-      let(:role2) { double("role", id: 2) }
+      let(:role1) { instance_double(Role, id: 1) }
+      let(:role2) { instance_double(Role, id: 2) }
       let(:roles) { [role1, role2] }
 
       it "is true if values are empty" do
         instance.values = []
 
-        expect(instance.fulfilled_by?(work_package, user))
-          .to be_truthy
+        expect(instance)
+          .to be_fulfilled_by(work_package, user)
       end
 
       it "is true if values the id of roles the user has in the work package's project" do
         instance.values = [1]
 
-        expect(instance.fulfilled_by?(work_package, user))
-          .to be_truthy
+        expect(instance)
+          .to be_fulfilled_by(work_package, user)
       end
 
       it "is false if values do not include work package's status_id" do
         instance.values = [5]
 
-        expect(instance.fulfilled_by?(work_package, user))
-          .to be_falsey
+        expect(instance)
+          .not_to be_fulfilled_by(work_package, user)
       end
     end
   end
diff --git a/spec/models/custom_actions/conditions/status_spec.rb b/spec/models/automations/conditions/status_spec.rb
similarity index 80%
rename from spec/models/custom_actions/conditions/status_spec.rb
rename to spec/models/automations/conditions/status_spec.rb
index a2620eb2afc0..8c46111f7e2b 100644
--- a/spec/models/custom_actions/conditions/status_spec.rb
+++ b/spec/models/automations/conditions/status_spec.rb
@@ -30,7 +30,7 @@
 require "spec_helper"
 require_relative "../shared_expectations"
 
-RSpec.describe CustomActions::Conditions::Status do
+RSpec.describe Automations::Conditions::Status do
   it_behaves_like "associated custom condition" do
     let(:key) { :status }
 
@@ -38,9 +38,7 @@
       it "is the list of all status" do
         statuses = [build_stubbed(:status),
                     build_stubbed(:status)]
-        allow(Status)
-          .to receive_message_chain(:select, :order)
-          .and_return(statuses)
+        allow(Status).to receive_messages(select: Status, order: statuses)
 
         expect(instance.allowed_values)
           .to eql([{ value: statuses.first.id, label: statuses.first.name },
@@ -49,28 +47,28 @@
     end
 
     describe "#fulfilled_by?" do
-      let(:work_package) { double("work_package", status_id: 1) }
-      let(:user) { double("not relevant") }
+      let(:work_package) { instance_double(WorkPackage, status_id: 1) }
+      let(:user) { instance_double(User) }
 
       it "is true if values are empty" do
         instance.values = []
 
-        expect(instance.fulfilled_by?(work_package, user))
-          .to be_truthy
+        expect(instance)
+          .to be_fulfilled_by(work_package, user)
       end
 
       it "is true if values include work package's status_id" do
         instance.values = [1]
 
-        expect(instance.fulfilled_by?(work_package, user))
-          .to be_truthy
+        expect(instance)
+          .to be_fulfilled_by(work_package, user)
       end
 
       it "is false if values do not include work package's status_id" do
         instance.values = [5]
 
-        expect(instance.fulfilled_by?(work_package, user))
-          .to be_falsey
+        expect(instance)
+          .not_to be_fulfilled_by(work_package, user)
       end
     end
   end
diff --git a/spec/models/custom_actions/conditions/type_spec.rb b/spec/models/automations/conditions/type_spec.rb
similarity index 84%
rename from spec/models/custom_actions/conditions/type_spec.rb
rename to spec/models/automations/conditions/type_spec.rb
index d974ad5e9fef..3740acd0cbd7 100644
--- a/spec/models/custom_actions/conditions/type_spec.rb
+++ b/spec/models/automations/conditions/type_spec.rb
@@ -30,7 +30,7 @@
 require "spec_helper"
 require_relative "../shared_expectations"
 
-RSpec.describe CustomActions::Conditions::Type do
+RSpec.describe Automations::Conditions::Type do
   it_behaves_like "associated custom condition" do
     let(:key) { :type }
 
@@ -50,28 +50,28 @@
     end
 
     describe "#fulfilled_by?" do
-      let(:work_package) { double("work_package", type_id: 1) }
-      let(:user) { double("not relevant") }
+      let(:work_package) { instance_double(WorkPackage, type_id: 1) }
+      let(:user) { instance_double(User) }
 
       it "is true if values are empty" do
         instance.values = []
 
-        expect(instance.fulfilled_by?(work_package, user))
-          .to be_truthy
+        expect(instance)
+          .to be_fulfilled_by(work_package, user)
       end
 
       it "is true if values include work package's type_id" do
         instance.values = [1]
 
-        expect(instance.fulfilled_by?(work_package, user))
-          .to be_truthy
+        expect(instance)
+          .to be_fulfilled_by(work_package, user)
       end
 
       it "is false if values do not include work package's type_id" do
         instance.values = [5]
 
-        expect(instance.fulfilled_by?(work_package, user))
-          .to be_falsey
+        expect(instance)
+          .not_to be_fulfilled_by(work_package, user)
       end
     end
   end
diff --git a/spec/models/custom_actions/shared_expectations.rb b/spec/models/automations/shared_expectations.rb
similarity index 92%
rename from spec/models/custom_actions/shared_expectations.rb
rename to spec/models/automations/shared_expectations.rb
index 59b35e158590..e4b358a67800 100644
--- a/spec/models/custom_actions/shared_expectations.rb
+++ b/spec/models/automations/shared_expectations.rb
@@ -28,7 +28,7 @@
 # See COPYRIGHT and LICENSE files for more details.
 #++
 
-RSpec.shared_context "custom actions action" do
+RSpec.shared_context "with an automation action" do
   let(:instance) do
     described_class.new
   end
@@ -49,7 +49,7 @@
 end
 
 RSpec.shared_examples_for "base custom action" do
-  include_context "custom actions action"
+  include_context "with an automation action"
   let(:expected_priority) do
     if defined?(priority)
       priority
@@ -125,18 +125,20 @@
 end
 
 RSpec.shared_examples_for "associated custom action" do
-  include_context "custom actions action" do
+  include_context "with an automation action" do
     describe "#apply" do
       let(:work_package) { build_stubbed(:work_package) }
 
       it "sets the associated_id in the work package to the action's value" do
-        expect(work_package)
-          .to receive(:"#{key}_id=")
-          .with(42)
+        allow(work_package).to receive(:"#{key}_id=")
 
         instance.values = 42
 
         instance.apply(work_package)
+
+        expect(work_package)
+          .to have_received(:"#{key}_id=")
+          .with(42)
       end
     end
 
@@ -156,7 +158,7 @@
 RSpec.shared_examples_for "associated custom action validations" do
   describe "#validate" do
     let(:errors) do
-      build_stubbed(:custom_action).errors
+      build_stubbed(:automation).errors
     end
 
     it "adds an error on actions if values is blank (depending on required?)" do
@@ -203,7 +205,7 @@
 RSpec.shared_examples_for "bool custom action validations" do
   describe "#validate" do
     let(:errors) do
-      build_stubbed(:custom_action).errors
+      build_stubbed(:automation).errors
     end
 
     it "adds an error on actions if values is blank (depending on required?)" do
@@ -248,7 +250,7 @@
 RSpec.shared_examples_for "int custom action validations" do
   describe "#validate" do
     let(:errors) do
-      build_stubbed(:custom_action).errors
+      build_stubbed(:automation).errors
     end
 
     it "adds an error on actions if values is blank (depending on required?)" do
@@ -284,7 +286,7 @@
 RSpec.shared_examples_for "float custom action validations" do
   describe "#validate" do
     let(:errors) do
-      build_stubbed(:custom_action).errors
+      build_stubbed(:automation).errors
     end
 
     it "adds an error on actions if values is blank (depending on required?)" do
@@ -320,7 +322,7 @@
 RSpec.shared_examples_for "string custom action validations" do
   describe "#validate" do
     let(:errors) do
-      build_stubbed(:custom_action).errors
+      build_stubbed(:automation).errors
     end
 
     it "adds an error on actions if values is blank (depending on required?)" do
@@ -361,7 +363,7 @@
   it_behaves_like "string custom action validations"
 
   let(:errors) do
-    build_stubbed(:custom_action).errors
+    build_stubbed(:automation).errors
   end
 
   it "adds an error on actions if value an invalid url" do
@@ -377,7 +379,7 @@
 RSpec.shared_examples_for "date custom action validations" do
   describe "#validate" do
     let(:errors) do
-      build_stubbed(:custom_action).errors
+      build_stubbed(:automation).errors
     end
 
     it "adds an error on actions if values is blank (depending on required?)" do
@@ -395,7 +397,7 @@
     end
 
     it "adds an error on actions if there are more values than one (depending on multi_value?)" do
-      instance.values = [Date.today + 4.days, Date.today - 5.days]
+      instance.values = [Time.zone.today + 4.days, Time.zone.today - 5.days]
 
       instance.validate(errors)
 
@@ -461,10 +463,10 @@
 RSpec.shared_examples_for "date values transformation" do
   describe "#values" do
     it "transforms the values to integers" do
-      instance.values = ["2015-03-29", Date.today, nil, (Date.today - 1.day).to_datetime, "bogus", "%CURRENT_DATE%"]
+      instance.values = ["2015-03-29", Time.zone.today, nil, (Time.zone.today - 1.day).to_datetime, "bogus", "%CURRENT_DATE%"]
 
       expect(instance.values)
-        .to contain_exactly(Date.parse("2015-03-29"), Date.today, nil, Date.today - 1.day, "%CURRENT_DATE%")
+        .to contain_exactly(Date.parse("2015-03-29"), Time.zone.today, nil, Time.zone.today - 1.day, "%CURRENT_DATE%")
     end
   end
 end
@@ -522,7 +524,7 @@
 
   describe "#validate" do
     let(:errors) do
-      build_stubbed(:custom_action).errors
+      build_stubbed(:automation).errors
     end
 
     it "adds an error on conditions if values not from list of allowed values" do
@@ -541,12 +543,12 @@
     let(:work_package) { build_stubbed(:work_package) }
 
     it "sets the daate to the action's value" do
-      instance.values = [Date.today + 5.days]
+      instance.values = [Time.zone.today + 5.days]
 
       instance.apply(work_package)
 
       expect(work_package.send(key))
-        .to eql Date.today + 5.days
+        .to eql Time.zone.today + 5.days
     end
 
     it "sets the date to the current date if so specified" do
@@ -555,7 +557,7 @@
       instance.apply(work_package)
 
       expect(work_package.send(key))
-        .to eql Date.today
+        .to eql Time.zone.today
     end
   end
 end
diff --git a/spec/models/permitted_params_spec.rb b/spec/models/permitted_params_spec.rb
index 8d226e435936..0c1cd0495c0e 100644
--- a/spec/models/permitted_params_spec.rb
+++ b/spec/models/permitted_params_spec.rb
@@ -463,8 +463,8 @@
     it_behaves_like "allows params"
   end
 
-  describe "#custom_action" do
-    let(:attribute) { :custom_action }
+  describe "#automation" do
+    let(:attribute) { :automation }
     let(:hash) do
       {
         "name" => "blubs",
diff --git a/spec/models/work_package/work_package_custom_actions_spec.rb b/spec/models/work_package/work_package_automations_spec.rb
similarity index 80%
rename from spec/models/work_package/work_package_custom_actions_spec.rb
rename to spec/models/work_package/work_package_automations_spec.rb
index e21bde3671d9..a1dc92f096fb 100644
--- a/spec/models/work_package/work_package_custom_actions_spec.rb
+++ b/spec/models/work_package/work_package_automations_spec.rb
@@ -30,7 +30,7 @@
 
 require "spec_helper"
 
-RSpec.describe WorkPackage, "custom_actions" do
+RSpec.describe WorkPackage, "automations" do
   let(:work_package) do
     build_stubbed(:work_package,
                   project:)
@@ -46,18 +46,18 @@
     create(:project_role)
   end
   let(:conditions) do
-    [CustomActions::Conditions::Status.new([status.id])]
+    [Automations::Conditions::Status.new([status.id])]
   end
 
-  let!(:custom_action) do
-    action = build(:custom_action)
+  let!(:automation) do
+    action = build(:automation)
     action.conditions = conditions
 
     action.save!
     action
   end
 
-  describe "#custom_actions" do
+  describe "#automations" do
     context "with the custom action having no restriction" do
       let(:conditions) do
         []
@@ -68,8 +68,8 @@
       end
 
       it "returns the action" do
-        expect(work_package.custom_actions(user))
-          .to contain_exactly(custom_action)
+        expect(work_package.automations(user))
+          .to contain_exactly(automation)
       end
     end
 
@@ -80,8 +80,8 @@
         end
 
         it "returns the action" do
-          expect(work_package.custom_actions(user))
-            .to contain_exactly(custom_action)
+          expect(work_package.automations(user))
+            .to contain_exactly(automation)
         end
       end
 
@@ -91,7 +91,7 @@
         end
 
         it "does not return the action" do
-          expect(work_package.custom_actions(user))
+          expect(work_package.automations(user))
             .to be_empty
         end
       end
@@ -99,13 +99,13 @@
 
     context "with a role restriction" do
       let(:conditions) do
-        [CustomActions::Conditions::Role.new(role.id)]
+        [Automations::Conditions::Role.new(role.id)]
       end
 
       context "with the user having the same role" do
         it "returns the action" do
-          expect(work_package.custom_actions(user))
-            .to contain_exactly(custom_action)
+          expect(work_package.automations(user))
+            .to contain_exactly(automation)
         end
       end
 
@@ -113,11 +113,11 @@
         let(:other_role) { create(:project_role) }
 
         let(:conditions) do
-          [CustomActions::Conditions::Role.new(other_role.id)]
+          [Automations::Conditions::Role.new(other_role.id)]
         end
 
         it "does not return the action" do
-          expect(work_package.custom_actions(user))
+          expect(work_package.automations(user))
             .to be_empty
         end
       end
diff --git a/spec/requests/api/v3/custom_actions/custom_actions_api_spec.rb b/spec/requests/api/v3/custom_actions/custom_actions_api_spec.rb
index 985a434d1138..172e18fddb72 100644
--- a/spec/requests/api/v3/custom_actions/custom_actions_api_spec.rb
+++ b/spec/requests/api/v3/custom_actions/custom_actions_api_spec.rb
@@ -48,7 +48,7 @@
     create(:user, member_with_roles: { project => role })
   end
   let(:action) do
-    create(:custom_action, actions: [CustomActions::Actions::AssignedTo.new(nil)])
+    create(:automation_with_manual_trigger, actions: [Automations::Actions::AssignedTo.new(nil)])
   end
   let(:parameters) do
     {
@@ -92,6 +92,22 @@
       end
     end
 
+    context "for an automation without manual trigger" do
+      let(:action) do
+        create(:automation_with_manual_trigger, actions: [Automations::Actions::AssignedTo.new(nil)]).tap do |automation|
+          automation.triggers.first.update_column(:type, "Automations::Triggers::Base")
+        end
+      end
+
+      before do
+        get api_v3_paths.custom_action(action.id)
+      end
+
+      it "is a 404 NOT FOUND" do
+        expect(last_response).to have_http_status(404)
+      end
+    end
+
     context "when lacking permissions" do
       let(:user) { create(:user) }
 
@@ -212,9 +228,9 @@
     context "when conditions are not fulfilled for the user" do
       let(:admin_role) { create(:project_role) }
       let(:action) do
-        create(:custom_action,
-               actions: [CustomActions::Actions::AssignedTo.new(nil)],
-               conditions: [CustomActions::Conditions::Role.new(admin_role.id)])
+        create(:automation,
+               actions: [Automations::Actions::AssignedTo.new(nil)],
+               conditions: [Automations::Conditions::Role.new(admin_role.id)])
       end
 
       include_context "post request"
diff --git a/spec/routing/custom_actions_spec.rb b/spec/routing/automations_spec.rb
similarity index 61%
rename from spec/routing/custom_actions_spec.rb
rename to spec/routing/automations_spec.rb
index 96a99d11c488..04b4bc969584 100644
--- a/spec/routing/custom_actions_spec.rb
+++ b/spec/routing/automations_spec.rb
@@ -30,46 +30,46 @@
 
 require "spec_helper"
 
-RSpec.describe "custom_actions routes" do
+RSpec.describe "automations routes" do
   describe "index" do
-    it "links GET /admin/custom_actions" do
-      expect(get("/admin/custom_actions"))
-        .to route_to("custom_actions#index")
+    it "links GET /admin/automations" do
+      expect(get("/admin/automations"))
+        .to route_to("automations#index")
     end
   end
 
   describe "new" do
-    it "links GET /admin/custom_actions/new" do
-      expect(get("/admin/custom_actions/new"))
-        .to route_to("custom_actions#new")
+    it "links GET /admin/automations/new" do
+      expect(get("/admin/automations/new"))
+        .to route_to("automations#new")
     end
   end
 
   describe "create" do
-    it "links POST /admin/custom_actions" do
-      expect(post("/admin/custom_actions"))
-        .to route_to("custom_actions#create")
+    it "links POST /admin/automations" do
+      expect(post("/admin/automations"))
+        .to route_to("automations#create")
     end
   end
 
   describe "edit" do
-    it "links GET /admin/custom_actions/:id/edit" do
-      expect(get("/admin/custom_actions/42/edit"))
-        .to route_to("custom_actions#edit", id: "42")
+    it "links GET /admin/automations/:id/edit" do
+      expect(get("/admin/automations/42/edit"))
+        .to route_to("automations#edit", id: "42")
     end
   end
 
   describe "update" do
-    it "links PATCH /admin/custom_actions/:id" do
-      expect(patch("/admin/custom_actions/42"))
-        .to route_to("custom_actions#update", id: "42")
+    it "links PATCH /admin/automations/:id" do
+      expect(patch("/admin/automations/42"))
+        .to route_to("automations#update", id: "42")
     end
   end
 
   describe "delete" do
-    it "links DELETE /admin/custom_actions/:id" do
-      expect(delete("/admin/custom_actions/42"))
-        .to route_to("custom_actions#destroy", id: "42")
+    it "links DELETE /admin/automations/:id" do
+      expect(delete("/admin/automations/42"))
+        .to route_to("automations#destroy", id: "42")
     end
   end
 end
diff --git a/spec/services/custom_actions/update_service_spec.rb b/spec/services/automations/update_service_spec.rb
similarity index 86%
rename from spec/services/custom_actions/update_service_spec.rb
rename to spec/services/automations/update_service_spec.rb
index d9d6e02de573..77e869832b8f 100644
--- a/spec/services/custom_actions/update_service_spec.rb
+++ b/spec/services/automations/update_service_spec.rb
@@ -30,9 +30,9 @@
 
 require "spec_helper"
 
-RSpec.describe CustomActions::UpdateService do
+RSpec.describe Automations::UpdateService do
   let(:action) do
-    action = build_stubbed(:custom_action)
+    action = build_stubbed(:automation)
 
     allow(action)
       .to receive(:save)
@@ -43,25 +43,21 @@
   let(:user) { build_stubbed(:user) }
   let(:save_success) { true }
   let(:contract_success) { true }
-  let(:contract_errors) { double("contract errors") }
+  let(:contract_errors) { instance_double(ActiveModel::Errors) }
   let(:instance) do
     contract
     described_class.new(action:, user:)
   end
   let(:contract) do
-    contract_instance = double("contract instance")
+    contract_instance = instance_double(Automations::CuContract)
 
-    allow(CustomActions::CuContract)
+    allow(Automations::CuContract)
       .to receive(:new)
-      .with(action)
+      .with(action, user)
       .and_return(contract_instance)
 
     allow(contract_instance)
-      .to receive(:validate)
-      .and_return(contract_success)
-    allow(contract_instance)
-      .to receive(:errors)
-      .and_return(contract_errors)
+      .to receive_messages(validate: contract_success, errors: contract_errors)
 
     contract_instance
   end
@@ -90,7 +86,7 @@
         .to be_success
     end
 
-    context "unsuccessful saving" do
+    context "when saving fails" do
       let(:save_success) { false }
 
       it "yields the result" do
@@ -107,7 +103,7 @@
       end
     end
 
-    context "unsuccessful contract" do
+    context "when the contract is invalid" do
       let(:contract_success) { false }
 
       it "yields the result" do
@@ -130,8 +126,8 @@
     end
 
     it "updates the actions" do
-      action.actions = [CustomActions::Actions::AssignedTo.new("1"),
-                        CustomActions::Actions::Status.new("3")]
+      action.actions = [Automations::Actions::AssignedTo.new("1"),
+                        Automations::Actions::Status.new("3")]
 
       new_actions = instance
                     .call(attributes: { actions: { assigned_to: ["2"], priority: ["3"] } })
@@ -158,7 +154,7 @@
       old_status = create(:status)
       new_status = create(:status)
 
-      action.conditions = [CustomActions::Conditions::Status.new(old_status.id)]
+      action.conditions = [Automations::Conditions::Status.new(old_status.id)]
 
       new_conditions = instance
                        .call(attributes: { conditions: { status: new_status.id } })
diff --git a/spec/services/custom_actions/update_work_package_service_spec.rb b/spec/services/automations/update_work_package_service_spec.rb
similarity index 84%
rename from spec/services/custom_actions/update_work_package_service_spec.rb
rename to spec/services/automations/update_work_package_service_spec.rb
index b62d97d16f8c..25abde60816d 100644
--- a/spec/services/custom_actions/update_work_package_service_spec.rb
+++ b/spec/services/automations/update_work_package_service_spec.rb
@@ -30,9 +30,9 @@
 
 require "spec_helper"
 
-RSpec.describe CustomActions::UpdateWorkPackageService do
-  let(:custom_action) do
-    action = build_stubbed(:custom_action)
+RSpec.describe Automations::UpdateWorkPackageService do
+  let(:automation) do
+    action = build_stubbed(:automation)
 
     allow(action)
       .to receive(:actions)
@@ -41,7 +41,7 @@
     action
   end
   let(:alter_action1) do
-    action = double("custom actions action 1", key: "abc", priority: 100)
+    action = instance_double(Automations::Actions::Base, key: "abc", priority: 100)
 
     allow(action)
       .to receive(:apply)
@@ -52,7 +52,7 @@
     action
   end
   let(:alter_action2) do
-    action = double("custom actions action 2", key: "def", priority: 10)
+    action = instance_double(Automations::Actions::Base, key: "def", priority: 10)
 
     allow(action)
       .to receive(:apply)
@@ -63,7 +63,7 @@
     action
   end
   let(:user) { build_stubbed(:user) }
-  let(:instance) { described_class.new(action: custom_action, user:) }
+  let(:instance) { described_class.new(action: automation, user:) }
   let(:update_service_call_implementation) do
     -> do
       result
@@ -90,7 +90,7 @@
   end
   let(:validation_result) { true }
   let!(:contract) do
-    contract = double("contract")
+    contract = instance_double(WorkPackages::UpdateContract)
 
     allow(WorkPackages::UpdateContract)
       .to receive(:new)
@@ -108,7 +108,8 @@
     let(:call) do
       instance.call(work_package:)
     end
-    let(:subject) { call }
+
+    subject { call }
 
     it "returns the update wp service result" do
       expect(call)
@@ -129,13 +130,9 @@
     end
 
     it "calls each registered action with the work package" do
-      [alter_action1, alter_action2].each do |alter_action|
-        expect(alter_action)
-          .to receive(:apply)
-          .with(work_package)
-      end
-
       call
+
+      expect([alter_action1, alter_action2]).to all(have_received(:apply).with(work_package))
     end
 
     it "calls the registered actions based on their priority" do
@@ -171,6 +168,8 @@
         subject
       end
 
+      # The lambda runs as the update service stub, so it must assert at call time
+      # rubocop:disable RSpec/ExpectInLet
       let(:update_service_call_implementation) do
         -> do
           # check that the work package retains only the valid changes
@@ -187,6 +186,7 @@
           result
         end
       end
+      # rubocop:enable RSpec/ExpectInLet
 
       it "is successful" do
         expect(subject)
@@ -198,6 +198,8 @@
       let(:result) do
         ServiceResult.failure(result: work_package)
       end
+      # The lambda runs as the update service stub, so it must assert at call time
+      # rubocop:disable RSpec/ExpectInLet
       let(:update_service_call_implementation) do
         -> do
           # check that the work package has all the changes
@@ -214,15 +216,11 @@
           result
         end
       end
+      # rubocop:enable RSpec/ExpectInLet
 
       before do
         allow(contract)
-          .to receive(:validate)
-          .and_return(false)
-
-        allow(contract)
-          .to receive(:errors)
-          .and_return(instance_double(ActiveModel::Errors, attribute_names: [:base]))
+          .to receive_messages(validate: false, errors: instance_double(ActiveModel::Errors, attribute_names: [:base]))
 
         work_package.lock_version = 200
 
diff --git a/spec/support/pages/admin/custom_actions/edit.rb b/spec/support/pages/admin/automations/edit.rb
similarity index 90%
rename from spec/support/pages/admin/custom_actions/edit.rb
rename to spec/support/pages/admin/automations/edit.rb
index ae2eb585433b..b6e195c16c6c 100644
--- a/spec/support/pages/admin/custom_actions/edit.rb
+++ b/spec/support/pages/admin/automations/edit.rb
@@ -34,16 +34,17 @@
 
 module Pages
   module Admin
-    module CustomActions
+    module Automations
       class Edit < Form
-        attr_reader :custom_action
+        attr_reader :automation
 
         def initialize(action)
-          @custom_action = action
+          super()
+          @automation = action
         end
 
         def path
-          edit_custom_action_path(id: custom_action.id)
+          edit_automation_path(id: automation.id)
         end
 
         def save
diff --git a/spec/support/pages/admin/custom_actions/form.rb b/spec/support/pages/admin/automations/form.rb
similarity index 87%
rename from spec/support/pages/admin/custom_actions/form.rb
rename to spec/support/pages/admin/automations/form.rb
index f2fef873c84b..d3f80c13c649 100644
--- a/spec/support/pages/admin/custom_actions/form.rb
+++ b/spec/support/pages/admin/automations/form.rb
@@ -33,7 +33,7 @@
 
 module Pages
   module Admin
-    module CustomActions
+    module Automations
       class Form < ::Pages::Page
         include ::Components::Autocompleter::NgSelectAutocompleteHelpers
 
@@ -45,10 +45,14 @@ def set_description(description)
           fill_in "Description", with: description
         end
 
+        def set_button_label(label)
+          fill_in "Button label", with: label
+        end
+
         def add_action(name, value)
           retry_block do
             select name, from: "Add action"
-            within "#custom-actions-form--active-actions" do
+            within "#automations-form--active-actions" do
               expect(page).to have_css(".form--label", text: name)
             end
           end
@@ -57,7 +61,7 @@ def add_action(name, value)
         end
 
         def remove_action(name)
-          within "#custom-actions-form--active-actions" do
+          within "#automations-form--active-actions" do
             find(".form--field", text: name)
               .click_on accessible_name: "Close"
           end
@@ -70,11 +74,11 @@ def expect_selected_option(value)
         def expect_action(name, value)
           value = "" if value.nil?
 
-          within "#custom-actions-form--actions" do
+          within "#automations-form--actions" do
             if value.is_a?(Array)
               value.each { |name| expect_selected_option(name.to_s) }
             else
-              element = find("input[name='custom_action[actions][#{name}]']", visible: :all)
+              element = find("input[name='automation[actions][#{name}]']", visible: :all)
               expect(element.value).to eq value.to_s
             end
           end
@@ -91,7 +95,7 @@ def set_condition(name, value)
             retry_block do
               set_condition_value(name, val)
 
-              within "#custom-actions-form--conditions" do
+              within "#automations-form--conditions" do
                 expect_selected_option val
               end
             end
@@ -101,13 +105,13 @@ def set_condition(name, value)
         private
 
         def set_action_value(name, value)
-          field = find("#custom-actions-form--active-actions .form--field", text: name, wait: 5)
+          field = find("#automations-form--active-actions .form--field", text: name, wait: 5)
 
           set_field_value(field, name, value)
         end
 
         def set_condition_value(name, value)
-          field = find("#custom-actions-form--conditions .form--field", text: name, wait: 5)
+          field = find("#automations-form--conditions .form--field", text: name, wait: 5)
 
           set_field_value(field, name, value)
         end
diff --git a/spec/support/pages/admin/custom_actions/index.rb b/spec/support/pages/admin/automations/index.rb
similarity index 89%
rename from spec/support/pages/admin/custom_actions/index.rb
rename to spec/support/pages/admin/automations/index.rb
index 5507daf97f5b..b57d143a5c1c 100644
--- a/spec/support/pages/admin/custom_actions/index.rb
+++ b/spec/support/pages/admin/automations/index.rb
@@ -32,14 +32,14 @@
 
 module Pages
   module Admin
-    module CustomActions
+    module Automations
       class Index < ::Pages::Page
         def new
-          page.find_test_selector("op-admin-custom-actions--button-new", text: "Custom action").click
+          page.find_test_selector("op-admin-automations--button-new").click
 
           wait_for_reload
 
-          Pages::Admin::CustomActions::New.new
+          Pages::Admin::Automations::New.new
         end
 
         def edit(name)
@@ -47,8 +47,8 @@ def edit(name)
             find(".icon-edit").click
           end
 
-          custom_action = CustomAction.find_by!(name:)
-          Pages::Admin::CustomActions::Edit.new(custom_action)
+          automation = Automation.find_by!(name:)
+          Pages::Admin::Automations::Edit.new(automation)
         end
 
         def delete(name)
@@ -63,7 +63,7 @@ def expect_listed(*names)
           within "table" do
             Array(names).each do |name|
               expect(page)
-                .to have_content name
+                .to have_text name
             end
           end
         end
@@ -97,7 +97,7 @@ def move_down(name)
         end
 
         def path
-          custom_actions_path
+          automations_path
         end
 
         private
diff --git a/spec/support/pages/admin/custom_actions/new.rb b/spec/support/pages/admin/automations/new.rb
similarity index 96%
rename from spec/support/pages/admin/custom_actions/new.rb
rename to spec/support/pages/admin/automations/new.rb
index 58be21a7c04b..cc4f713427b2 100644
--- a/spec/support/pages/admin/custom_actions/new.rb
+++ b/spec/support/pages/admin/automations/new.rb
@@ -34,14 +34,14 @@
 
 module Pages
   module Admin
-    module CustomActions
+    module Automations
       class New < Form
         def create
           click_button "Create"
         end
 
         def path
-          new_custom_action_path
+          new_automation_path
         end
       end
     end
diff --git a/spec/support/pages/work_packages/abstract_work_package.rb b/spec/support/pages/work_packages/abstract_work_package.rb
index 2c2f61ed076a..9da3b3450490 100644
--- a/spec/support/pages/work_packages/abstract_work_package.rb
+++ b/spec/support/pages/work_packages/abstract_work_package.rb
@@ -190,22 +190,22 @@ def expect_no_zen_mode
       expect(page).to have_css(".op-app-header")
     end
 
-    def expect_custom_action(name)
+    def expect_automation(name)
       expect(page)
         .to have_css(".custom-action", text: name)
     end
 
-    def expect_custom_action_disabled(name)
+    def expect_automation_disabled(name)
       expect(page)
         .to have_css(".custom-action [disabled]", text: name)
     end
 
-    def expect_no_custom_action(name)
+    def expect_no_automation(name)
       expect(page)
         .to have_no_css(".custom-action", text: name)
     end
 
-    def expect_custom_action_order(*names)
+    def expect_automation_order(*names)
       within(".custom-actions") do
         names.each_cons(2) do |earlier, later|
           body.index(earlier) < body.index(later)
@@ -286,7 +286,7 @@ def visit_copy!
       page
     end
 
-    def click_custom_action(name, expect_success: true)
+    def click_automation(name, expect_success: true)
       page.within(".custom-actions") do
         click_button(name)
       end

From a8cbe56bd8d34e6c12c5e275fb706f1c3023a0ab Mon Sep 17 00:00:00 2001
From: =?UTF-8?q?Oliver=20G=C3=BCnther?= <mail@oliverguenther.de>
Date: Tue, 8 Sep 2026 12:53:24 +0200
Subject: [PATCH 2/3] Use more fitting manual trigger selection

---
 app/components/automations/row_component.rb   |  9 +--
 app/models/automation.rb                      |  4 +
 app/models/automations/register.rb            |  6 ++
 app/models/automations/triggers/base.rb       | 12 +++
 app/views/automations/_form.html.erb          | 15 ++--
 .../_trigger_fields_manual.html.erb           |  3 -
 config/locales/en.yml                         |  1 +
 .../automations_controller_spec.rb            | 44 +++++++++++
 .../automations/automations_spec.rb           |  3 +
 .../automations/triggers/manual_spec.rb       | 79 +++++++++++++++++++
 .../update_work_package_service_spec.rb       |  6 +-
 spec/support/pages/admin/automations/form.rb  | 18 +++++
 12 files changed, 180 insertions(+), 20 deletions(-)
 create mode 100644 spec/models/automations/triggers/manual_spec.rb

diff --git a/app/components/automations/row_component.rb b/app/components/automations/row_component.rb
index 5bd09372d89a..f00b4d26e8f5 100644
--- a/app/components/automations/row_component.rb
+++ b/app/components/automations/row_component.rb
@@ -39,14 +39,7 @@ def name
     end
 
     def triggers
-      automation.triggers.map do |trigger|
-        case trigger
-        when Automations::Triggers::Manual
-          I18n.t("automations.triggers.manual.label")
-        else
-          trigger.type.demodulize
-        end
-      end.join(", ")
+      automation.triggers.map(&:human_name).join(", ")
     end
 
     def conditions
diff --git a/app/models/automation.rb b/app/models/automation.rb
index cae2ddf36ef0..de0e7491ae43 100644
--- a/app/models/automation.rb
+++ b/app/models/automation.rb
@@ -86,6 +86,10 @@ def self.order_by_position
     order(:position)
   end
 
+  def available_triggers
+    ::Automations::Register.triggers
+  end
+
   def all_actions
     all_of(available_actions, actions)
   end
diff --git a/app/models/automations/register.rb b/app/models/automations/register.rb
index 0645fa7dc24e..18aee3b00f82 100644
--- a/app/models/automations/register.rb
+++ b/app/models/automations/register.rb
@@ -48,6 +48,12 @@ def actions
       ]
     end
 
+    def triggers
+      [
+        Automations::Triggers::Manual
+      ]
+    end
+
     def conditions
       [
         Automations::Conditions::Status,
diff --git a/app/models/automations/triggers/base.rb b/app/models/automations/triggers/base.rb
index cc9d2958d6e4..38ec9e84d8c2 100644
--- a/app/models/automations/triggers/base.rb
+++ b/app/models/automations/triggers/base.rb
@@ -36,6 +36,18 @@ class Base < ApplicationRecord
       belongs_to :automation, inverse_of: :triggers
 
       acts_as_list scope: :automation
+
+      validates :type, inclusion: { in: ->(_) { Automations::Register.triggers.map(&:name) } }
+
+      def self.key
+        name.demodulize.underscore.to_sym
+      end
+
+      def self.human_name
+        I18n.t("automations.triggers.#{key}.label", default: name.demodulize)
+      end
+
+      delegate :key, :human_name, to: :class
     end
   end
 end
diff --git a/app/views/automations/_form.html.erb b/app/views/automations/_form.html.erb
index 857ab1133c84..426a02d2d7ad 100644
--- a/app/views/automations/_form.html.erb
+++ b/app/views/automations/_form.html.erb
@@ -29,6 +29,7 @@ See COPYRIGHT and LICENSE files for more details.
 
 <% active_section_keys = @automation.actions.map(&:key) %>
 <% trigger = @automation.triggers.detect { |t| t.is_a?(Automations::Triggers::Manual) } || @automation.triggers.build(type: "Automations::Triggers::Manual") %>
+<% trigger_options = @automation.available_triggers.map { |klass| [klass.human_name, klass.name] } %>
 
 <div class="form--field -required">
   <%= f.text_field :name, required: true, container_class: "-middle" %>
@@ -40,14 +41,18 @@ See COPYRIGHT and LICENSE files for more details.
 <fieldset class="form--fieldset" id="automations-form--trigger">
   <legend class="form--fieldset-legend"><%= t("automations.trigger") %></legend>
   <div class="form--field">
-    <%= styled_label_tag "automation_trigger_type", t("automations.triggers.name"), class: "-top" %>
+    <%= styled_label_tag "automation_triggers_attributes_0_type", t("automations.triggers.name"), class: "-top" %>
     <div class="form--field-container">
-      <%= styled_text_field_tag "automation_trigger_type",
-                                t("automations.triggers.manual.label"),
-                                disabled: true,
-                                container_class: "-middle" %>
+      <%= styled_select_tag "automation[triggers_attributes][0][type]",
+                            options_for_select(trigger_options, trigger.type),
+                            container_class: "-middle",
+                            aria: { describedby: "automation_triggers_attributes_0_type_instructions" } %>
+    </div>
+    <div class="form--field-instructions" id="automation_triggers_attributes_0_type_instructions">
+      <%= t("automations.triggers.more_coming") %>
     </div>
   </div>
+  <%= hidden_field_tag "automation[triggers_attributes][0][id]", trigger.id if trigger.persisted? %>
   <%= render partial: "trigger_fields_manual", locals: { trigger: } %>
 </fieldset>
 
diff --git a/app/views/automations/_trigger_fields_manual.html.erb b/app/views/automations/_trigger_fields_manual.html.erb
index 35e4a2dd8346..e2849689c445 100644
--- a/app/views/automations/_trigger_fields_manual.html.erb
+++ b/app/views/automations/_trigger_fields_manual.html.erb
@@ -27,9 +27,6 @@ See COPYRIGHT and LICENSE files for more details.
 
 ++#%>
 
-<%= hidden_field_tag "automation[triggers_attributes][0][type]", "Automations::Triggers::Manual" %>
-<%= hidden_field_tag "automation[triggers_attributes][0][id]", trigger.id if trigger.persisted? %>
-
 <div class="form--field -required">
   <%= styled_label_tag "automation_triggers_attributes_0_options_button_label", t("automations.triggers.manual.button_label"), class: "-top" %>
   <div class="form--field-container">
diff --git a/config/locales/en.yml b/config/locales/en.yml
index 6ebd9c780384..c39bfefda1fe 100644
--- a/config/locales/en.yml
+++ b/config/locales/en.yml
@@ -2221,6 +2221,7 @@ en:
       manual:
         button_label: "Button label"
         label: "Manual button click"
+      more_coming: "OpenProject will add more trigger types soon."
       name: "Triggers"
 
   background_jobs:
diff --git a/spec/controllers/automations_controller_spec.rb b/spec/controllers/automations_controller_spec.rb
index 147d0db1eac8..94d794340b35 100644
--- a/spec/controllers/automations_controller_spec.rb
+++ b/spec/controllers/automations_controller_spec.rb
@@ -435,4 +435,48 @@
 
     it_behaves_like "403 for non admins"
   end
+
+  describe "the trigger field" do
+    render_views
+
+    let(:automation) { create(:automation) }
+
+    before do
+      login_as(admin)
+    end
+
+    shared_examples_for "a trigger select" do
+      it "offers every registered trigger type" do
+        options = response.parsed_body
+                          .css("select[name='automation[triggers_attributes][0][type]'] option")
+
+        expect(options.map { |option| [option.text, option[:value]] })
+          .to eq([["Manual button click", "Automations::Triggers::Manual"]])
+      end
+
+      it "explains that more trigger types are coming" do
+        expect(response.body)
+          .to include(I18n.t("automations.triggers.more_coming"))
+      end
+    end
+
+    context "on a new automation" do
+      before { get(:new) }
+
+      it_behaves_like "a trigger select"
+    end
+
+    context "on an existing automation" do
+      before { get(:edit, params: { id: automation.id }) }
+
+      it_behaves_like "a trigger select"
+
+      it "preselects the stored trigger type" do
+        selected = response.parsed_body
+                           .at_css("select[name='automation[triggers_attributes][0][type]'] option[selected]")
+
+        expect(selected[:value]).to eq("Automations::Triggers::Manual")
+      end
+    end
+  end
 end
diff --git a/spec/features/work_packages/automations/automations_spec.rb b/spec/features/work_packages/automations/automations_spec.rb
index 5a78e77ab414..af77df62e8c4 100644
--- a/spec/features/work_packages/automations/automations_spec.rb
+++ b/spec/features/work_packages/automations/automations_spec.rb
@@ -151,6 +151,9 @@
 
     new_ca_page = index_ca_page.new
 
+    new_ca_page.expect_trigger_options("Manual button click")
+    new_ca_page.expect_trigger_instructions
+
     new_ca_page.set_name("Unassign")
     new_ca_page.set_button_label("Unassign")
     new_ca_page.set_description("Removes the assignee")
diff --git a/spec/models/automations/triggers/manual_spec.rb b/spec/models/automations/triggers/manual_spec.rb
new file mode 100644
index 000000000000..6a6292831462
--- /dev/null
+++ b/spec/models/automations/triggers/manual_spec.rb
@@ -0,0 +1,79 @@
+# frozen_string_literal: true
+
+#-- copyright
+# OpenProject is an open source project management software.
+# Copyright (C) the OpenProject GmbH
+#
+# This program is free software; you can redistribute it and/or
+# modify it under the terms of the GNU General Public License version 3.
+#
+# OpenProject is a fork of ChiliProject, which is a fork of Redmine. The copyright follows:
+# Copyright (C) 2006-2013 Jean-Philippe Lang
+# Copyright (C) 2010-2013 the ChiliProject Team
+#
+# This program is free software; you can redistribute it and/or
+# modify it under the terms of the GNU General Public License
+# as published by the Free Software Foundation; either version 2
+# of the License, or (at your option) any later version.
+#
+# This program is distributed in the hope that it will be useful,
+# but WITHOUT ANY WARRANTY; without even the implied warranty of
+# MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the
+# GNU General Public License for more details.
+#
+# You should have received a copy of the GNU General Public License
+# along with this program; if not, write to the Free Software
+# Foundation, Inc., 51 Franklin Street, Fifth Floor, Boston, MA  02110-1301, USA.
+#
+# See COPYRIGHT and LICENSE files for more details.
+#++
+
+require "spec_helper"
+
+RSpec.describe Automations::Triggers::Manual do
+  describe ".key" do
+    it "derives from the class name" do
+      expect(described_class.key).to eq(:manual)
+    end
+  end
+
+  describe ".human_name" do
+    it "is the translated label" do
+      expect(described_class.human_name).to eq("Manual button click")
+    end
+
+    it "falls back to the class name when no translation exists" do
+      expect(Automations::Triggers::Base.human_name).to eq("Base")
+    end
+  end
+
+  describe "#human_name" do
+    it "delegates to the class" do
+      expect(described_class.new.human_name).to eq("Manual button click")
+    end
+  end
+
+  describe "type" do
+    let(:automation) { build(:automation) }
+
+    it "accepts a registered trigger type" do
+      trigger = automation.triggers.detect { |t| t.is_a?(described_class) }
+
+      expect(trigger).to be_valid
+    end
+
+    it "rejects a type that is not registered" do
+      trigger = automation.triggers.first
+      trigger.type = "Automations::Triggers::Base"
+
+      expect(trigger).not_to be_valid
+      expect(trigger.errors.symbols_for(:type)).to include(:inclusion)
+    end
+
+    it "makes the automation invalid" do
+      automation.triggers.first.type = "Automations::Triggers::Base"
+
+      expect(automation).not_to be_valid
+    end
+  end
+end
diff --git a/spec/services/automations/update_work_package_service_spec.rb b/spec/services/automations/update_work_package_service_spec.rb
index 25abde60816d..b93c7ac33ebf 100644
--- a/spec/services/automations/update_work_package_service_spec.rb
+++ b/spec/services/automations/update_work_package_service_spec.rb
@@ -169,7 +169,7 @@
       end
 
       # The lambda runs as the update service stub, so it must assert at call time
-      # rubocop:disable RSpec/ExpectInLet
+      # rubocop:disable-next RSpec/ExpectInLet
       let(:update_service_call_implementation) do
         -> do
           # check that the work package retains only the valid changes
@@ -186,7 +186,6 @@
           result
         end
       end
-      # rubocop:enable RSpec/ExpectInLet
 
       it "is successful" do
         expect(subject)
@@ -199,7 +198,7 @@
         ServiceResult.failure(result: work_package)
       end
       # The lambda runs as the update service stub, so it must assert at call time
-      # rubocop:disable RSpec/ExpectInLet
+      # rubocop:disable-next RSpec/ExpectInLet
       let(:update_service_call_implementation) do
         -> do
           # check that the work package has all the changes
@@ -216,7 +215,6 @@
           result
         end
       end
-      # rubocop:enable RSpec/ExpectInLet
 
       before do
         allow(contract)
diff --git a/spec/support/pages/admin/automations/form.rb b/spec/support/pages/admin/automations/form.rb
index d3f80c13c649..6b4c047e9d2e 100644
--- a/spec/support/pages/admin/automations/form.rb
+++ b/spec/support/pages/admin/automations/form.rb
@@ -49,6 +49,24 @@ def set_button_label(label)
           fill_in "Button label", with: label
         end
 
+        def set_trigger(label)
+          select label, from: "Triggers"
+        end
+
+        def expect_trigger_options(*labels)
+          field = page.find_field("Triggers")
+
+          expect(field).not_to be_disabled
+          expect(field.all("option").map(&:text)).to eq(Array(labels))
+        end
+
+        def expect_trigger_instructions
+          within "#automations-form--trigger" do
+            expect(page).to have_css(".form--field-instructions",
+                                     text: I18n.t("automations.triggers.more_coming"))
+          end
+        end
+
         def add_action(name, value)
           retry_block do
             select name, from: "Add action"

From c9613000faaa6ef5c4f3169f26f064ed29230901 Mon Sep 17 00:00:00 2001
From: =?UTF-8?q?Oliver=20G=C3=BCnther?= <mail@oliverguenther.de>
Date: Tue, 12 May 2026 10:22:33 +0200
Subject: [PATCH 3/3] Update automation actions to be separate STI table

---
 app/contracts/automations/cu_contract.rb      |   5 +-
 app/models/automation.rb                      |  23 ++-
 app/models/automations/actions/base.rb        |  35 +++--
 .../automations/actions/custom_field.rb       | 102 +++++-------
 .../actions/custom_field/for_associated.rb    |   5 +
 .../actions/custom_field/for_boolean.rb       |   6 +
 .../actions/custom_field/for_date.rb          |   6 +
 .../actions/custom_field/for_float.rb         |   6 +
 .../actions/custom_field/for_integer.rb       |   6 +
 .../actions/custom_field/for_link.rb          |   6 +
 .../actions/custom_field/for_string.rb        |   6 +
 .../actions/custom_field/for_text.rb          |   6 +
 .../actions/custom_field/for_user.rb          |   5 +
 app/models/automations/actions/done_ratio.rb  |   2 +-
 app/models/automations/actions/serializer.rb  |  57 -------
 .../automations/actions/strategies/date.rb    |   2 +-
 .../actions/strategies/me_associated.rb       |   4 +-
 app/services/automations/base_service.rb      |  49 +++---
 ...8_convert_custom_actions_to_automations.rb | 147 +++++++++++++++++-
 .../contracts/automations/cu_contract_spec.rb |   7 +-
 .../automations/automations_spec.rb           |   6 +-
 .../work_package_representer_spec.rb          |   4 +-
 spec/models/automation_spec.rb                |  11 +-
 .../automations/actions/custom_field_spec.rb  |  37 ++---
 .../strategies/user_custom_field_spec.rb      |   4 +-
 .../models/automations/shared_expectations.rb |  10 +-
 .../custom_actions/custom_actions_api_spec.rb |   6 +-
 .../automations/update_service_spec.rb        |   7 +-
 28 files changed, 329 insertions(+), 241 deletions(-)
 create mode 100644 app/models/automations/actions/custom_field/for_associated.rb
 create mode 100644 app/models/automations/actions/custom_field/for_boolean.rb
 create mode 100644 app/models/automations/actions/custom_field/for_date.rb
 create mode 100644 app/models/automations/actions/custom_field/for_float.rb
 create mode 100644 app/models/automations/actions/custom_field/for_integer.rb
 create mode 100644 app/models/automations/actions/custom_field/for_link.rb
 create mode 100644 app/models/automations/actions/custom_field/for_string.rb
 create mode 100644 app/models/automations/actions/custom_field/for_text.rb
 create mode 100644 app/models/automations/actions/custom_field/for_user.rb
 delete mode 100644 app/models/automations/actions/serializer.rb

diff --git a/app/contracts/automations/cu_contract.rb b/app/contracts/automations/cu_contract.rb
index 69801603a09d..b3b22e0d3898 100644
--- a/app/contracts/automations/cu_contract.rb
+++ b/app/contracts/automations/cu_contract.rb
@@ -40,8 +40,9 @@ def self.model
     attribute :description
 
     attribute :actions do
-      errors.add(:actions, :empty) if model.actions.empty?
-      model.actions.each { |action| action.validate(errors) }
+      live_actions = model.actions.reject(&:marked_for_destruction?)
+      errors.add(:actions, :empty) if live_actions.empty?
+      live_actions.each { |action| action.validate(errors) }
     end
 
     attribute :conditions do
diff --git a/app/models/automation.rb b/app/models/automation.rb
index de0e7491ae43..89cb99d0ca22 100644
--- a/app/models/automation.rb
+++ b/app/models/automation.rb
@@ -33,7 +33,6 @@ class Automation < ApplicationRecord
   validate :must_have_at_least_one_trigger
   validate :must_not_have_more_than_one_manual_trigger
 
-  serialize :actions, coder: Automations::Actions::Serializer
   before_validation :ensure_manual_trigger
 
   # This code was moved from custom actions and it's decisions unchanged
@@ -51,6 +50,13 @@ class Automation < ApplicationRecord
            inverse_of: :automation
   accepts_nested_attributes_for :triggers
 
+  has_many :actions,
+           -> { order(:position, :id) },
+           class_name: "Automations::Actions::Base",
+           dependent: :destroy,
+           inverse_of: :automation
+  accepts_nested_attributes_for :actions, allow_destroy: true
+
   after_save :persist_conditions
 
   attribute :conditions
@@ -62,22 +68,11 @@ class Automation < ApplicationRecord
     joins(:triggers).where(automation_triggers: { type: "Automations::Triggers::Manual" }).distinct
   }
 
-  def initialize(*args)
-    ret = super
-    self.actions ||= []
-    ret
-  end
-
   def reload(*args)
     @conditions = nil
     super
   end
 
-  def actions=(values)
-    actions_will_change!
-    super
-  end
-
   def self.order_by_name
     order(:name)
   end
@@ -95,7 +90,7 @@ def all_actions
   end
 
   def available_actions
-    ::Automations::Register.actions.map(&:all).flatten
+    ::Automations::Register.actions.flat_map(&:templates)
   end
 
   def all_conditions
@@ -135,7 +130,7 @@ def all_of(availables, actual)
     availables.map do |available|
       existing = actual.detect { |a| a.key == available.key }
 
-      existing || available.new
+      existing || (available.is_a?(Class) ? available.new : available)
     end
   end
 
diff --git a/app/models/automations/actions/base.rb b/app/models/automations/actions/base.rb
index ea78ba237067..b3a8edc089ed 100644
--- a/app/models/automations/actions/base.rb
+++ b/app/models/automations/actions/base.rb
@@ -28,17 +28,24 @@
 # See COPYRIGHT and LICENSE files for more details.
 #++
 
-class Automations::Actions::Base
-  attr_reader :values
+class Automations::Actions::Base < ApplicationRecord
+  self.table_name = "automation_actions"
 
   DEFAULT_PRIORITY = 100
 
-  def initialize(values = [])
-    self.values = values
+  belongs_to :automation, inverse_of: :actions
+  acts_as_list scope: :automation
+
+  store_attribute :options, :values
+
+  after_initialize :coerce_persisted_values
+
+  def values
+    Array(super)
   end
 
-  def values=(values)
-    @values = Array(values)
+  def write_raw_values(new_values)
+    self.options = options.is_a?(Hash) ? options.merge("values" => Array(new_values)) : { "values" => Array(new_values) }
   end
 
   def allowed_values
@@ -67,14 +74,8 @@ def self.key
     raise SubclassResponsibilityError
   end
 
-  def self.all
-    [self]
-  end
-
-  def self.for(key)
-    if key == self.key
-      self
-    end
+  def self.templates
+    [new]
   end
 
   delegate :key, to: :class
@@ -102,6 +103,12 @@ def deconstruct_keys(*)
     { type:, custom_field_based: respond_to?(:custom_field) }
   end
 
+  def coerce_persisted_values
+    return if new_record? || values.empty?
+
+    self.values = values
+  end
+
   def validate_value_required(errors)
     if required? && values.empty?
       errors.add :actions,
diff --git a/app/models/automations/actions/custom_field.rb b/app/models/automations/actions/custom_field.rb
index 1872cac30125..bc88a0a27bcc 100644
--- a/app/models/automations/actions/custom_field.rb
+++ b/app/models/automations/actions/custom_field.rb
@@ -29,78 +29,51 @@
 #++
 
 class Automations::Actions::CustomField < Automations::Actions::Base
-  class << self
-    def key
-      custom_field.attribute_name.to_sym
+  store_attribute :options, :custom_field_id, :integer
+
+  FORMAT_TO_SUBCLASS = {
+    "string" => "Automations::Actions::CustomField::ForString",
+    "text" => "Automations::Actions::CustomField::ForText",
+    "link" => "Automations::Actions::CustomField::ForLink",
+    "int" => "Automations::Actions::CustomField::ForInteger",
+    "float" => "Automations::Actions::CustomField::ForFloat",
+    "date" => "Automations::Actions::CustomField::ForDate",
+    "bool" => "Automations::Actions::CustomField::ForBoolean",
+    "user" => "Automations::Actions::CustomField::ForUser",
+    "list" => "Automations::Actions::CustomField::ForAssociated",
+    "version" => "Automations::Actions::CustomField::ForAssociated"
+  }.freeze
+
+  def self.templates
+    WorkPackageCustomField.usable_as_automation.filter_map do |cf|
+      subclass = subclass_for(cf)
+      next unless subclass
+
+      template = subclass.new(custom_field_id: cf.id)
+      template.instance_variable_set(:@custom_field, cf)
+      template
     end
+  end
 
-    def custom_field
-      raise SubclassResponsibilityError
-    end
-
-    def all
-      WorkPackageCustomField
-        .usable_as_automation
-        .map do |cf|
-          create_subclass(cf)
-        end
-    end
-
-    def for(key)
-      match_result = key.match /custom_field_(\d+)/
-
-      if match_result && (cf = WorkPackageCustomField.find_by(id: match_result[1]))
-        create_subclass(cf)
-      end
-    end
-
-    private
-
-    def create_subclass(custom_field)
-      klass = Class.new(Automations::Actions::CustomField)
-      klass.define_singleton_method(:custom_field) do
-        custom_field
-      end
+  def self.subclass_for(custom_field)
+    name = FORMAT_TO_SUBCLASS[custom_field.field_format]
+    name&.constantize
+  end
 
-      klass.include(strategy(custom_field))
-      klass
-    end
+  def custom_field
+    return nil if custom_field_id.blank?
+    return @custom_field if defined?(@custom_field)
 
-    def strategy(custom_field)
-      case custom_field.field_format
-      when "string"
-        Automations::Actions::Strategies::String
-      when "text"
-        Automations::Actions::Strategies::Text
-      when "link"
-        Automations::Actions::Strategies::Link
-      when "int"
-        Automations::Actions::Strategies::Integer
-      when "float"
-        Automations::Actions::Strategies::Float
-      when "date"
-        Automations::Actions::Strategies::Date
-      when "bool"
-        Automations::Actions::Strategies::Boolean
-      when "user"
-        Automations::Actions::Strategies::UserCustomField
-      when "list", "version"
-        Automations::Actions::Strategies::AssociatedCustomField
-      end
-    end
+    @custom_field = WorkPackageCustomField.find_by(id: custom_field_id)
   end
 
-  delegate :custom_field, to: :class
-
-  def human_name
-    custom_field.name
+  def key
+    cf = custom_field
+    cf ? cf.attribute_name.to_sym : :inexistent_custom_field
   end
 
-  def apply(work_package)
-    if work_package.respond_to?(custom_field.attribute_setter)
-      set_custom_field_value(work_package)
-      validate_custom_field(work_package)
-    end
+  def human_name
+    custom_field&.name || super
   end
 
   private
@@ -110,7 +83,6 @@ def set_custom_field_value(work_package)
   end
 
   def validate_custom_field(work_package)
-    # Validate the custom field the custom action is changing.
     work_package.custom_values_to_validate += Array(work_package.custom_value_for(custom_field))
   end
 end
diff --git a/app/models/automations/actions/custom_field/for_associated.rb b/app/models/automations/actions/custom_field/for_associated.rb
new file mode 100644
index 000000000000..ac24f90d2b9b
--- /dev/null
+++ b/app/models/automations/actions/custom_field/for_associated.rb
@@ -0,0 +1,5 @@
+# frozen_string_literal: true
+
+class Automations::Actions::CustomField::ForAssociated < Automations::Actions::CustomField
+  include Automations::Actions::Strategies::AssociatedCustomField
+end
diff --git a/app/models/automations/actions/custom_field/for_boolean.rb b/app/models/automations/actions/custom_field/for_boolean.rb
new file mode 100644
index 000000000000..f6eebfecc9eb
--- /dev/null
+++ b/app/models/automations/actions/custom_field/for_boolean.rb
@@ -0,0 +1,6 @@
+# frozen_string_literal: true
+
+class Automations::Actions::CustomField::ForBoolean < Automations::Actions::CustomField
+  include Automations::Actions::Strategies::Boolean
+  include Automations::Actions::Strategies::CustomField
+end
diff --git a/app/models/automations/actions/custom_field/for_date.rb b/app/models/automations/actions/custom_field/for_date.rb
new file mode 100644
index 000000000000..bdcdf1bfa2ee
--- /dev/null
+++ b/app/models/automations/actions/custom_field/for_date.rb
@@ -0,0 +1,6 @@
+# frozen_string_literal: true
+
+class Automations::Actions::CustomField::ForDate < Automations::Actions::CustomField
+  include Automations::Actions::Strategies::CustomField
+  include Automations::Actions::Strategies::Date
+end
diff --git a/app/models/automations/actions/custom_field/for_float.rb b/app/models/automations/actions/custom_field/for_float.rb
new file mode 100644
index 000000000000..fd793dfb4b96
--- /dev/null
+++ b/app/models/automations/actions/custom_field/for_float.rb
@@ -0,0 +1,6 @@
+# frozen_string_literal: true
+
+class Automations::Actions::CustomField::ForFloat < Automations::Actions::CustomField
+  include Automations::Actions::Strategies::Float
+  include Automations::Actions::Strategies::CustomField
+end
diff --git a/app/models/automations/actions/custom_field/for_integer.rb b/app/models/automations/actions/custom_field/for_integer.rb
new file mode 100644
index 000000000000..e280efbc572a
--- /dev/null
+++ b/app/models/automations/actions/custom_field/for_integer.rb
@@ -0,0 +1,6 @@
+# frozen_string_literal: true
+
+class Automations::Actions::CustomField::ForInteger < Automations::Actions::CustomField
+  include Automations::Actions::Strategies::Integer
+  include Automations::Actions::Strategies::CustomField
+end
diff --git a/app/models/automations/actions/custom_field/for_link.rb b/app/models/automations/actions/custom_field/for_link.rb
new file mode 100644
index 000000000000..7af4e73c2ee0
--- /dev/null
+++ b/app/models/automations/actions/custom_field/for_link.rb
@@ -0,0 +1,6 @@
+# frozen_string_literal: true
+
+class Automations::Actions::CustomField::ForLink < Automations::Actions::CustomField
+  include Automations::Actions::Strategies::Link
+  include Automations::Actions::Strategies::CustomField
+end
diff --git a/app/models/automations/actions/custom_field/for_string.rb b/app/models/automations/actions/custom_field/for_string.rb
new file mode 100644
index 000000000000..6b4ffd316c0d
--- /dev/null
+++ b/app/models/automations/actions/custom_field/for_string.rb
@@ -0,0 +1,6 @@
+# frozen_string_literal: true
+
+class Automations::Actions::CustomField::ForString < Automations::Actions::CustomField
+  include Automations::Actions::Strategies::String
+  include Automations::Actions::Strategies::CustomField
+end
diff --git a/app/models/automations/actions/custom_field/for_text.rb b/app/models/automations/actions/custom_field/for_text.rb
new file mode 100644
index 000000000000..1ad39881bcf6
--- /dev/null
+++ b/app/models/automations/actions/custom_field/for_text.rb
@@ -0,0 +1,6 @@
+# frozen_string_literal: true
+
+class Automations::Actions::CustomField::ForText < Automations::Actions::CustomField
+  include Automations::Actions::Strategies::Text
+  include Automations::Actions::Strategies::CustomField
+end
diff --git a/app/models/automations/actions/custom_field/for_user.rb b/app/models/automations/actions/custom_field/for_user.rb
new file mode 100644
index 000000000000..e393a3f91410
--- /dev/null
+++ b/app/models/automations/actions/custom_field/for_user.rb
@@ -0,0 +1,5 @@
+# frozen_string_literal: true
+
+class Automations::Actions::CustomField::ForUser < Automations::Actions::CustomField
+  include Automations::Actions::Strategies::UserCustomField
+end
diff --git a/app/models/automations/actions/done_ratio.rb b/app/models/automations/actions/done_ratio.rb
index d51ecec36b95..36e5fcfb0f25 100644
--- a/app/models/automations/actions/done_ratio.rb
+++ b/app/models/automations/actions/done_ratio.rb
@@ -47,7 +47,7 @@ def maximum
     100
   end
 
-  def self.all
+  def self.templates
     if WorkPackage.work_based_mode?
       super
     else
diff --git a/app/models/automations/actions/serializer.rb b/app/models/automations/actions/serializer.rb
deleted file mode 100644
index 1905419e896b..000000000000
--- a/app/models/automations/actions/serializer.rb
+++ /dev/null
@@ -1,57 +0,0 @@
-# frozen_string_literal: true
-
-#-- copyright
-# OpenProject is an open source project management software.
-# Copyright (C) the OpenProject GmbH
-#
-# This program is free software; you can redistribute it and/or
-# modify it under the terms of the GNU General Public License version 3.
-#
-# OpenProject is a fork of ChiliProject, which is a fork of Redmine. The copyright follows:
-# Copyright (C) 2006-2013 Jean-Philippe Lang
-# Copyright (C) 2010-2013 the ChiliProject Team
-#
-# This program is free software; you can redistribute it and/or
-# modify it under the terms of the GNU General Public License
-# as published by the Free Software Foundation; either version 2
-# of the License, or (at your option) any later version.
-#
-# This program is distributed in the hope that it will be useful,
-# but WITHOUT ANY WARRANTY; without even the implied warranty of
-# MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the
-# GNU General Public License for more details.
-#
-# You should have received a copy of the GNU General Public License
-# along with this program; if not, write to the Free Software
-# Foundation, Inc., 51 Franklin Street, Fifth Floor, Boston, MA  02110-1301, USA.
-#
-# See COPYRIGHT and LICENSE files for more details.
-#++
-
-module Automations::Actions::Serializer
-  module_function
-
-  def load(value)
-    return [] unless value
-
-    YAML
-      .safe_load(value, permitted_classes: [Symbol, Date])
-      .filter_map do |key, values|
-      klass = nil
-
-      Automations::Register
-        .actions
-        .detect do |a|
-        klass = a.for(key)
-      end
-
-      klass ||= Automations::Actions::Inexistent
-
-      klass.new(values)
-    end
-  end
-
-  def dump(actions)
-    YAML::dump(actions.map { |a| [a.key, a.values.map(&:to_s)] })
-  end
-end
diff --git a/app/models/automations/actions/strategies/date.rb b/app/models/automations/actions/strategies/date.rb
index c69632e86d07..e91e6b6f23b4 100644
--- a/app/models/automations/actions/strategies/date.rb
+++ b/app/models/automations/actions/strategies/date.rb
@@ -38,7 +38,7 @@ def type
   end
 
   def apply(work_package)
-    accessor = :"#{self.class.key}="
+    accessor = :"#{key}="
     if work_package.respond_to? accessor
       work_package.send(accessor, date_to_apply)
     end
diff --git a/app/models/automations/actions/strategies/me_associated.rb b/app/models/automations/actions/strategies/me_associated.rb
index 9d36a8fb6d5f..0a5e7a2e070c 100644
--- a/app/models/automations/actions/strategies/me_associated.rb
+++ b/app/models/automations/actions/strategies/me_associated.rb
@@ -40,7 +40,7 @@ def associated
   end
 
   def values=(values)
-    values = Array(values).map do |v|
+    cast = Array(values).map do |v|
       if v == current_user_value_key
         v
       else
@@ -48,7 +48,7 @@ def values=(values)
       end
     end
 
-    @values = values.uniq
+    write_raw_values(cast.uniq)
   end
 
   ##
diff --git a/app/services/automations/base_service.rb b/app/services/automations/base_service.rb
index 02449a8dbd33..fb705ca3e280 100644
--- a/app/services/automations/base_service.rb
+++ b/app/services/automations/base_service.rb
@@ -59,36 +59,31 @@ def set_attributes(action, attributes)
     set_triggers(action, triggers_attributes)
   end
 
-  def set_actions(action, actions_attributes)
-    existing_action_keys = action.actions.map(&:key)
+  def set_actions(automation, actions_attributes)
+    existing_by_key = automation.actions.index_by(&:key)
+    incoming_keys = actions_attributes.keys.map(&:to_sym)
 
-    remove_actions(action, existing_action_keys - actions_attributes.keys)
-    update_actions(action, actions_attributes.slice(*existing_action_keys))
-    add_actions(action, actions_attributes.slice(*(actions_attributes.keys - existing_action_keys)))
-  end
-
-  def remove_actions(action, keys)
-    keys.each { |key| remove_action(action, key) }
-  end
-
-  def update_actions(action, key_values)
-    key_values.each { |key, values| update_action(action, key, values) }
-  end
-
-  def add_actions(action, key_values)
-    key_values.each { |key, values| add_action(action, key, values) }
-  end
+    (existing_by_key.keys - incoming_keys).each do |key|
+      existing_by_key[key].mark_for_destruction
+    end
 
-  def update_action(action, key, values)
-    action.actions.detect { |a| a.key == key }.values = values
+    actions_attributes.each do |key, values|
+      key = key.to_sym
+      if (existing = existing_by_key[key])
+        existing.values = values
+      else
+        add_action(automation, key, values)
+      end
+    end
   end
 
-  def add_action(action, key, values)
-    action.actions << available_action_for(action, key).new(values)
-  end
+  def add_action(automation, key, values)
+    template = automation.available_actions.detect { |a| a.key == key } ||
+               Automations::Actions::Inexistent.new
 
-  def remove_action(action, key)
-    action.actions.reject! { |a| a.key == key }
+    new_action = template.dup
+    new_action.values = values
+    automation.actions << new_action
   end
 
   def set_conditions(action, conditions_attributes)
@@ -97,10 +92,6 @@ def set_conditions(action, conditions_attributes)
     end
   end
 
-  def available_action_for(action, key)
-    action.available_actions.detect { |a| a.key == key } || Automations::Actions::Inexistent
-  end
-
   def available_condition_for(action, key)
     action.available_conditions.detect { |a| a.key == key } || Automations::Conditions::Inexistent
   end
diff --git a/db/migrate/20260907113318_convert_custom_actions_to_automations.rb b/db/migrate/20260907113318_convert_custom_actions_to_automations.rb
index 1703a031afd6..39f5544b21fe 100644
--- a/db/migrate/20260907113318_convert_custom_actions_to_automations.rb
+++ b/db/migrate/20260907113318_convert_custom_actions_to_automations.rb
@@ -33,6 +33,34 @@
 class ConvertCustomActionsToAutomations < ActiveRecord::Migration[8.1]
   include Migration::Utils
 
+  ACTION_KEY_TO_STI = {
+    "assigned_to" => "Automations::Actions::AssignedTo",
+    "responsible" => "Automations::Actions::Responsible",
+    "status" => "Automations::Actions::Status",
+    "priority" => "Automations::Actions::Priority",
+    "type" => "Automations::Actions::Type",
+    "project" => "Automations::Actions::Project",
+    "notify" => "Automations::Actions::Notify",
+    "done_ratio" => "Automations::Actions::DoneRatio",
+    "estimated_hours" => "Automations::Actions::EstimatedHours",
+    "start_date" => "Automations::Actions::StartDate",
+    "due_date" => "Automations::Actions::DueDate",
+    "date" => "Automations::Actions::Date"
+  }.freeze
+
+  CUSTOM_FIELD_FORMAT_TO_STI = {
+    "string" => "Automations::Actions::CustomField::ForString",
+    "text" => "Automations::Actions::CustomField::ForText",
+    "link" => "Automations::Actions::CustomField::ForLink",
+    "int" => "Automations::Actions::CustomField::ForInteger",
+    "float" => "Automations::Actions::CustomField::ForFloat",
+    "date" => "Automations::Actions::CustomField::ForDate",
+    "bool" => "Automations::Actions::CustomField::ForBoolean",
+    "user" => "Automations::Actions::CustomField::ForUser",
+    "list" => "Automations::Actions::CustomField::ForAssociated",
+    "version" => "Automations::Actions::CustomField::ForAssociated"
+  }.freeze
+
   JOIN_TABLES = {
     statuses: :status_id,
     roles: :role_id,
@@ -49,6 +77,16 @@ class MigrationTrigger < ApplicationRecord
     self.inheritance_column = nil
   end
 
+  class MigrationAction < ApplicationRecord
+    self.table_name = "automation_actions"
+    self.inheritance_column = nil
+  end
+
+  class MigrationCustomField < ApplicationRecord
+    self.table_name = "custom_fields"
+    self.inheritance_column = nil
+  end
+
   def up
     rename_table :custom_actions, :automations
 
@@ -57,6 +95,30 @@ def up
                         :custom_action_id, :automation_id, other_column)
     end
 
+    create_trigger_table
+    create_action_table
+    backfill_triggers_and_actions
+
+    remove_column :automations, :actions
+  end
+
+  def down
+    restore_serialized_actions
+
+    drop_table :automation_actions
+    drop_table :automation_triggers
+
+    JOIN_TABLES.reverse_each do |suffix, other_column|
+      rename_join_table(:"automations_#{suffix}", :"custom_actions_#{suffix}",
+                        :automation_id, :custom_action_id, other_column)
+    end
+
+    rename_table :automations, :custom_actions
+  end
+
+  private
+
+  def create_trigger_table
     create_table :automation_triggers do |t|
       t.references :automation, null: false, foreign_key: true, index: true
       t.string :type, null: false
@@ -65,9 +127,23 @@ def up
 
       t.timestamps
     end
+  end
+
+  def create_action_table
+    create_table :automation_actions do |t|
+      t.references :automation, null: false, foreign_key: true, index: true
+      t.string :type, null: false
+      t.jsonb :options, null: false, default: {}
+      t.integer :position
+
+      t.timestamps
+    end
+  end
 
+  def backfill_triggers_and_actions
     MigrationAutomation.reset_column_information
     MigrationTrigger.reset_column_information
+    MigrationAction.reset_column_information
 
     MigrationAutomation.find_each do |automation|
       MigrationTrigger.create!(
@@ -76,21 +152,78 @@ def up
         options: { button_label: automation.name },
         position: 1
       )
+
+      backfill_actions(automation)
     end
   end
 
-  def down
-    drop_table :automation_triggers
+  def restore_serialized_actions
+    add_column :automations, :actions, :text
 
-    JOIN_TABLES.reverse_each do |suffix, other_column|
-      rename_join_table(:"automations_#{suffix}", :"custom_actions_#{suffix}",
-                        :automation_id, :custom_action_id, other_column)
+    MigrationAutomation.reset_column_information
+
+    MigrationAutomation.find_each do |automation|
+      entries = MigrationAction
+        .where(automation_id: automation.id)
+        .order(:position, :id)
+        .pluck(:type, :options)
+        .filter_map { |type, options| serialize_action(type, options) }
+
+      automation.update_column(:actions, YAML.dump(entries))
     end
+  end
 
-    rename_table :automations, :custom_actions
+  def backfill_actions(automation)
+    raw = automation[:actions]
+    return if raw.blank?
+
+    parsed = YAML.safe_load(raw, permitted_classes: [Symbol, Date, ActiveSupport::HashWithIndifferentAccess])
+    return unless parsed.is_a?(Array)
+
+    parsed.each_with_index do |entry, index|
+      key, values = entry
+      type, options = resolve_action(key, values)
+      next unless type
+
+      MigrationAction.create!(
+        automation_id: automation.id,
+        type:,
+        options:,
+        position: index + 1
+      )
+    end
   end
 
-  private
+  def resolve_action(key, values)
+    key_str = key.to_s
+    if (sti = ACTION_KEY_TO_STI[key_str])
+      [sti, { values: Array(values) }]
+    elsif (match = key_str.match(/\Acustom_field_(\d+)\z/))
+      resolve_custom_field_action(match[1].to_i, values)
+    end
+  end
+
+  def resolve_custom_field_action(custom_field_id, values)
+    cf = MigrationCustomField.find_by(id: custom_field_id)
+    return unless cf
+
+    sti = CUSTOM_FIELD_FORMAT_TO_STI[cf.field_format]
+    return unless sti
+
+    [sti, { custom_field_id:, values: Array(values) }]
+  end
+
+  def serialize_action(type, options)
+    options = options.is_a?(Hash) ? options.with_indifferent_access : {}
+    values = Array(options["values"]).map(&:to_s)
+
+    if (key = ACTION_KEY_TO_STI.invert[type])
+      [key, values]
+    elsif type.start_with?("Automations::Actions::CustomField::")
+      cf_id = options["custom_field_id"]
+      ["custom_field_#{cf_id}", values] if cf_id
+    end
+  end
 
   # rename_table and rename_column already take care of renaming the Rails-default indexes.
   # So we only have to normalize possibly remaining indexes here
diff --git a/spec/contracts/automations/cu_contract_spec.rb b/spec/contracts/automations/cu_contract_spec.rb
index e2ab078276d6..436f3e359388 100644
--- a/spec/contracts/automations/cu_contract_spec.rb
+++ b/spec/contracts/automations/cu_contract_spec.rb
@@ -36,8 +36,7 @@
 
   let(:user) { build_stubbed(:user) }
   let(:action) do
-    build_stubbed(:automation, actions:
-                              [Automations::Actions::AssignedTo.new])
+    build(:automation, actions: [Automations::Actions::AssignedTo.new])
   end
   let(:contract) { described_class.new(action, user) }
 
@@ -79,13 +78,13 @@
     end
 
     it "requires a value if the action requires one" do
-      action.actions = [Automations::Actions::Status.new([])]
+      action.actions = [Automations::Actions::Status.new(values: [])]
 
       expect_contract_invalid actions: :empty
     end
 
     it "allows only the allowed values" do
-      status_action = Automations::Actions::Status.new([0])
+      status_action = Automations::Actions::Status.new(values: [0])
       allow(status_action)
         .to receive(:allowed_values)
         .and_return([{ value: nil, label: "-" },
diff --git a/spec/features/work_packages/automations/automations_spec.rb b/spec/features/work_packages/automations/automations_spec.rb
index af77df62e8c4..36a9cef81d62 100644
--- a/spec/features/work_packages/automations/automations_spec.rb
+++ b/spec/features/work_packages/automations/automations_spec.rb
@@ -550,7 +550,7 @@
 
     before do
       create(:automation,
-             actions: [Automations::Actions::AssignedTo.new(value: nil)],
+             actions: [Automations::Actions::AssignedTo.new],
              name: "Unassign")
     end
 
@@ -590,7 +590,7 @@
           with_settings: { work_packages_identifier: "semantic" } do
     let!(:unassign_ca) do
       create(:automation,
-             actions: [Automations::Actions::AssignedTo.new(nil)],
+             actions: [Automations::Actions::AssignedTo.new],
              name: "Unassign")
     end
 
@@ -600,7 +600,7 @@
              project: project,
              roles: [role])
       create(:automation,
-             actions: [Automations::Actions::Responsible.new("current_user")],
+             actions: [Automations::Actions::Responsible.new(values: ["current_user"])],
              name: "Be responsible")
     end
 
diff --git a/spec/lib/api/v3/work_packages/work_package_representer_spec.rb b/spec/lib/api/v3/work_packages/work_package_representer_spec.rb
index 8edcd5a2c3c3..0c20b15af34d 100644
--- a/spec/lib/api/v3/work_packages/work_package_representer_spec.rb
+++ b/spec/lib/api/v3/work_packages/work_package_representer_spec.rb
@@ -1586,7 +1586,7 @@
     describe "customActions" do
       it "has a collection of customActions" do
         unassign_action = build_stubbed(:automation,
-                                        actions: [Automations::Actions::AssignedTo.new(value: nil)],
+                                        actions: [Automations::Actions::AssignedTo.new],
                                         name: "Unassign")
         allow(work_package)
           .to receive(:automations)
@@ -1701,7 +1701,7 @@
     describe "customActions" do
       it "has an array of customActions" do
         unassign_action = build_stubbed(:automation,
-                                        actions: [Automations::Actions::AssignedTo.new(value: nil)],
+                                        actions: [Automations::Actions::AssignedTo.new],
                                         name: "Unassign")
         allow(work_package)
           .to receive(:automations)
diff --git a/spec/models/automation_spec.rb b/spec/models/automation_spec.rb
index f9946349738f..46d8c0587672 100644
--- a/spec/models/automation_spec.rb
+++ b/spec/models/automation_spec.rb
@@ -32,6 +32,7 @@
 
 RSpec.describe Automation do
   let(:stubbed_instance) { build_stubbed(:automation) }
+  let(:in_memory_instance) { build(:automation) }
   let(:instance) { create(:automation, name: "zzzzzzzzz") }
   let(:other_instance) { create(:automation, name: "aaaaa") }
 
@@ -95,14 +96,14 @@
     end
 
     it "can be set and read" do
-      stubbed_instance.actions = [Automations::Actions::AssignedTo.new(1)]
+      in_memory_instance.actions = [Automations::Actions::AssignedTo.new(values: [1])]
 
-      expect(stubbed_instance.actions.map { |a| [a.key, a.values] })
+      expect(in_memory_instance.actions.map { |a| [a.key, a.values] })
         .to contain_exactly([:assigned_to, [1]])
     end
 
     it "can be persisted" do
-      instance.actions = [Automations::Actions::AssignedTo.new(1)]
+      instance.actions = [Automations::Actions::AssignedTo.new(values: [1])]
 
       instance.save!
 
@@ -118,9 +119,9 @@
     end
 
     it "returns the activated actions with their selected value and all other with the default value" do
-      stubbed_instance.actions = [Automations::Actions::AssignedTo.new(1)]
+      in_memory_instance.actions = [Automations::Actions::AssignedTo.new(values: [1])]
 
-      expect(stubbed_instance.all_actions.map { |a| [a.key, a.values] })
+      expect(in_memory_instance.all_actions.map { |a| [a.key, a.values] })
         .to include([:assigned_to, [1]], [:status, []])
     end
 
diff --git a/spec/models/automations/actions/custom_field_spec.rb b/spec/models/automations/actions/custom_field_spec.rb
index 07f205da059f..c4309d6e7bb4 100644
--- a/spec/models/automations/actions/custom_field_spec.rb
+++ b/spec/models/automations/actions/custom_field_spec.rb
@@ -89,39 +89,30 @@
   let(:klass) do
     allow(WorkPackageCustomField)
       .to receive(:find_by)
-      .with(id: custom_field.id.to_s)
+      .with(id: custom_field.id)
       .and_return(custom_field)
 
-    described_class.for(custom_field.attribute_name)
+    described_class.subclass_for(custom_field)
   end
   let(:instance) do
-    klass.new
+    klass.new(custom_field_id: custom_field.id)
   end
 
-  describe ".all" do
+  describe ".templates" do
     before do
       allow(WorkPackageCustomField)
         .to receive(:usable_as_automation)
         .and_return(custom_fields)
     end
 
-    it "is an array with a list of subclasses for every custom_field" do
-      expect(described_class.all.length)
+    it "is an array of template instances for every custom_field" do
+      expect(described_class.templates.length)
         .to eql custom_fields.length
 
-      expect(described_class.all.map(&:custom_field))
+      expect(described_class.templates.map(&:custom_field))
         .to match_array(custom_fields)
 
-      described_class.all.each do |subclass|
-        expect(subclass.ancestors).to include(described_class)
-      end
-    end
-  end
-
-  describe ".key" do
-    it "is the custom field accessor" do
-      expect(klass.key)
-        .to eql(custom_field.attribute_getter)
+      expect(described_class.templates).to all(be_a(described_class))
     end
   end
 
@@ -134,7 +125,7 @@
 
   describe "#value" do
     it "can be provided on initialization" do
-      i = klass.new(1)
+      i = klass.new(custom_field_id: custom_field.id, values: [1])
 
       expect(i.values)
         .to eql [1]
@@ -683,7 +674,7 @@
 
       it "adds the custom value to custom_values_to_validate when applying the action" do
         # Create the action instance for our created custom field
-        action_instance = described_class.for(custom_field.attribute_name).new
+        action_instance = described_class.subclass_for(custom_field).new(custom_field_id: custom_field.id)
         action_instance.values = ["test value"]
 
         # Initially, custom_values_to_validate should be empty for persisted work packages
@@ -699,7 +690,7 @@
       it "does not add to custom_values_to_validate if work package doesn't respond to the setter" do
         # Create a work package that doesn't have this custom field
         other_work_package = create(:work_package)
-        action_instance = described_class.for(custom_field.attribute_name).new
+        action_instance = described_class.subclass_for(custom_field).new(custom_field_id: custom_field.id)
         action_instance.values = ["test value"]
 
         expect(other_work_package.custom_values_to_validate).to be_empty
@@ -712,7 +703,9 @@
 
       context "with multiple custom actions" do
         let(:another_custom_field) { create(:string_wp_custom_field) }
-        let(:another_instance) { described_class.for(another_custom_field.attribute_name).new }
+        let(:another_instance) do
+          described_class.subclass_for(another_custom_field).new(custom_field_id: another_custom_field.id)
+        end
 
         before do
           work_package.project.work_package_custom_fields << another_custom_field
@@ -720,7 +713,7 @@
         end
 
         it "accumulates custom values in custom_values_to_validate" do
-          action_instance = described_class.for(custom_field.attribute_name).new
+          action_instance = described_class.subclass_for(custom_field).new(custom_field_id: custom_field.id)
           action_instance.values = ["first value"]
           another_instance.values = ["second value"]
 
diff --git a/spec/models/automations/actions/strategies/user_custom_field_spec.rb b/spec/models/automations/actions/strategies/user_custom_field_spec.rb
index eceae4867ba4..fb8c5d4a6c99 100644
--- a/spec/models/automations/actions/strategies/user_custom_field_spec.rb
+++ b/spec/models/automations/actions/strategies/user_custom_field_spec.rb
@@ -31,8 +31,8 @@ module Strategies
           end
         end
 
-        let(:user_cf_action) { Automations::Actions::CustomField.for("custom_field_#{user_cf.id}").new }
-        let(:multi_user_cf_action) { Automations::Actions::CustomField.for("custom_field_#{multi_user_cf.id}").new }
+        let(:user_cf_action) { Automations::Actions::CustomField.subclass_for(user_cf).new(custom_field_id: user_cf.id) }
+        let(:multi_user_cf_action) { Automations::Actions::CustomField.subclass_for(multi_user_cf).new(custom_field_id: multi_user_cf.id) }
         let(:single_user_work_package) { create(:work_package, project: single_user_project) }
         let(:multi_user_work_package) { create(:work_package, project: multi_user_project) }
 
diff --git a/spec/models/automations/shared_expectations.rb b/spec/models/automations/shared_expectations.rb
index e4b358a67800..b3bb676f5c52 100644
--- a/spec/models/automations/shared_expectations.rb
+++ b/spec/models/automations/shared_expectations.rb
@@ -65,10 +65,10 @@
     end
   end
 
-  describe ".all" do
-    it "is an array with the class itself" do
-      expect(described_class.all)
-        .to contain_exactly(described_class)
+  describe ".templates" do
+    it "is an array with a template instance of the class" do
+      expect(described_class.templates)
+        .to contain_exactly(an_instance_of(described_class))
     end
   end
 
@@ -88,7 +88,7 @@
 
   describe "#values" do
     it "can be provided on initialization" do
-      i = described_class.new(expected_value)
+      i = described_class.new(values: [expected_value])
 
       expect(i.values)
         .to eql [expected_value]
diff --git a/spec/requests/api/v3/custom_actions/custom_actions_api_spec.rb b/spec/requests/api/v3/custom_actions/custom_actions_api_spec.rb
index 172e18fddb72..1f1a92bc29a9 100644
--- a/spec/requests/api/v3/custom_actions/custom_actions_api_spec.rb
+++ b/spec/requests/api/v3/custom_actions/custom_actions_api_spec.rb
@@ -48,7 +48,7 @@
     create(:user, member_with_roles: { project => role })
   end
   let(:action) do
-    create(:automation_with_manual_trigger, actions: [Automations::Actions::AssignedTo.new(nil)])
+    create(:automation_with_manual_trigger, actions: [Automations::Actions::AssignedTo.new])
   end
   let(:parameters) do
     {
@@ -94,7 +94,7 @@
 
     context "for an automation without manual trigger" do
       let(:action) do
-        create(:automation_with_manual_trigger, actions: [Automations::Actions::AssignedTo.new(nil)]).tap do |automation|
+        create(:automation_with_manual_trigger, actions: [Automations::Actions::AssignedTo.new]).tap do |automation|
           automation.triggers.first.update_column(:type, "Automations::Triggers::Base")
         end
       end
@@ -229,7 +229,7 @@
       let(:admin_role) { create(:project_role) }
       let(:action) do
         create(:automation,
-               actions: [Automations::Actions::AssignedTo.new(nil)],
+               actions: [Automations::Actions::AssignedTo.new],
                conditions: [Automations::Conditions::Role.new(admin_role.id)])
       end
 
diff --git a/spec/services/automations/update_service_spec.rb b/spec/services/automations/update_service_spec.rb
index 77e869832b8f..cbe4748638cc 100644
--- a/spec/services/automations/update_service_spec.rb
+++ b/spec/services/automations/update_service_spec.rb
@@ -32,7 +32,7 @@
 
 RSpec.describe Automations::UpdateService do
   let(:action) do
-    action = build_stubbed(:automation)
+    action = build(:automation)
 
     allow(action)
       .to receive(:save)
@@ -126,13 +126,14 @@
     end
 
     it "updates the actions" do
-      action.actions = [Automations::Actions::AssignedTo.new("1"),
-                        Automations::Actions::Status.new("3")]
+      action.actions = [Automations::Actions::AssignedTo.new(values: ["1"]),
+                        Automations::Actions::Status.new(values: ["3"])]
 
       new_actions = instance
                     .call(attributes: { actions: { assigned_to: ["2"], priority: ["3"] } })
                     .result
                     .actions
+                    .reject(&:marked_for_destruction?)
                     .map { |a| [a.key, a.values] }
 
       expect(new_actions)