diff --git a/apps/web/src/agent-deploy.ts b/apps/web/src/agent-deploy.ts
index 3d38dc915..60a09e470 100644
--- a/apps/web/src/agent-deploy.ts
+++ b/apps/web/src/agent-deploy.ts
@@ -19,7 +19,6 @@ const GitTokenMintShape = type({ id: "string", secret: "string" });
 const TenantDomainShape = type({ domain: "string" });
 
 const PUSH_TOKEN_LIFETIME_MS = 10 * 60 * 1000;
-const AGENT_TURN_TIMEOUT_MS = 2 * 60 * 1000;
 
 async function readErrorBody(response: Response): Promise<string> {
   const body: unknown = await response.json().catch(() => undefined);
@@ -111,7 +110,9 @@ export function buildAgentDefinitionJson(args: {
           toolPackagePins: [],
         },
         drainBehavior: "wait",
-        timeout: AGENT_TURN_TIMEOUT_MS,
+        // No `timeout`: it stays armed across an approval park, so any
+        // finite value aborts a run waiting on a person to answer an
+        // ask-gated tool call (see agents/myra/src/index.ts).
         triggers: "unbounded",
         input: { from: "trigger.payload" },
       },
diff --git a/apps/web/src/pages/agents-page.tsx b/apps/web/src/pages/agents-page.tsx
index e9f54442f..fa2e38568 100644
--- a/apps/web/src/pages/agents-page.tsx
+++ b/apps/web/src/pages/agents-page.tsx
@@ -17,14 +17,16 @@ import {
   TableHead,
   TableHeader,
   TableRow,
+  toast,
 } from "@corbits/react-ui";
 import { Robot } from "@/lib/icons";
 import { useMutation, useQueryClient } from "@tanstack/react-query";
+import { reportError } from "@corbits/error-sink";
 
 import { QueryView } from "@/lib/api-query";
 import { chatKeys, chatPath } from "../chat-path";
 import { isAgentNotRunning, listChatAgents, type ChatAgent } from "@/chat/threads-api";
-import { redeployRoomAgent } from "../workbench-create";
+import { describeRestartFailure, redeployRoomAgent } from "../workbench-create";
 import { useBench } from "../bench-context";
 import { Link } from "../navigation";
 import { useTenantQuery } from "../routines-api";
@@ -57,6 +59,10 @@ export function AgentsRosterList({
     onSuccess: () => {
       void queryClient.invalidateQueries({ queryKey: chatKeys.agents(tenantId) });
     },
+    onError: (cause) => {
+      reportError(cause, { operation: "agent_restart", tenantId });
+      toast(describeRestartFailure(cause));
+    },
   });
   if (agents.length === 0) {
     return (
diff --git a/apps/web/src/pages/chat-thread-page.tsx b/apps/web/src/pages/chat-thread-page.tsx
index 1e449358e..559822140 100644
--- a/apps/web/src/pages/chat-thread-page.tsx
+++ b/apps/web/src/pages/chat-thread-page.tsx
@@ -2,10 +2,11 @@
 // first message (agent picked in the select, or by @tagging one in the
 // message itself); `/chats/:id` is the transcript plus a reply box.
 
-import { Button, EmptyState, PageShell, Select } from "@corbits/react-ui";
+import { Button, EmptyState, PageShell, Select, toast } from "@corbits/react-ui";
 import { WarningCircle } from "@/lib/icons";
 import { useMutation, useQuery, useQueryClient } from "@tanstack/react-query";
 import { useEffect, useMemo, useState } from "react";
+import { reportError } from "@corbits/error-sink";
 
 import { ApprovalRow } from "@/chat/approval-row";
 import { IdentityAvatar } from "@/chat/avatar";
@@ -25,7 +26,7 @@ import {
   type ChatAgent,
 } from "@/chat/threads-api";
 import { MYRA_SOURCE_CONFIG } from "../myra-source";
-import { redeployRoomAgent } from "../workbench-create";
+import { describeRestartFailure, redeployRoomAgent } from "../workbench-create";
 import { useBench } from "../bench-context";
 import { chatIdFromPath, chatKeys, chatPath, NEW_CHAT_PATH } from "../chat-path";
 import { usePendingApprovals } from "../pending-approvals";
@@ -74,6 +75,10 @@ function NewChat({
     onSuccess: () => {
       void queryClient.invalidateQueries({ queryKey: chatKeys.agents(tenantId) });
     },
+    onError: (cause) => {
+      reportError(cause, { operation: "agent_restart", tenantId });
+      toast(describeRestartFailure(cause));
+    },
   });
 
   const defaultAgent = agents.find((agent) => agent.name === MYRA_SOURCE_CONFIG.displayName);
@@ -207,6 +212,10 @@ function ChatTranscript({
       void queryClient.invalidateQueries({ queryKey: chatKeys.agents(tenantId) });
       void queryClient.invalidateQueries({ queryKey: chatKeys.one(tenantId, chatId) });
     },
+    onError: (cause) => {
+      reportError(cause, { operation: "agent_restart", tenantId });
+      toast(describeRestartFailure(cause));
+    },
   });
 
   if (chatQuery.isError && chat === undefined) {
diff --git a/apps/web/src/shell/first-run-tour.tsx b/apps/web/src/shell/first-run-tour.tsx
index 213356bf8..175148b5b 100644
--- a/apps/web/src/shell/first-run-tour.tsx
+++ b/apps/web/src/shell/first-run-tour.tsx
@@ -86,6 +86,11 @@ export function FirstRunTour({ userId }: { readonly userId: string }) {
       continuous
       showSkipButton
       disableOverlayClose
+      // The overlay otherwise swallows every click outside the spotlight —
+      // real app chrome (e.g. a roster row's Chat link) is reachable at
+      // any point in the shell, tour running or not, so clicks must pass
+      // through to it rather than land on the tour's own backdrop.
+      spotlightClicks
       spotlightPadding={6}
       callback={handleCallback}
       styles={{
diff --git a/apps/web/src/workbench-create.ts b/apps/web/src/workbench-create.ts
index 65842658c..604917d1d 100644
--- a/apps/web/src/workbench-create.ts
+++ b/apps/web/src/workbench-create.ts
@@ -124,6 +124,17 @@ export async function createWorkbench(input: CreateWorkbenchInput): Promise<stri
   return tenantId;
 }
 
+const GENERIC_RESTART_FAILURE = "Couldn't restart this agent. Try again.";
+
+/** Allow-lists what is safe to show verbatim: only the authored stage
+ * copy, never a raw request path or schema summary. */
+export function describeRestartFailure(cause: unknown): string {
+  if (!(cause instanceof WorkbenchCreateError)) return GENERIC_RESTART_FAILURE;
+  return cause.stage === "deploy"
+    ? "This agent couldn't be deployed. Try again."
+    : GENERIC_RESTART_FAILURE;
+}
+
 /** A hub restart releases every process-provisioned deployment; this
  * redeploys one room agent through the same path `createWorkbench` used,
  * re-running it against the tenant its asset already lives in. */