Cowork AI OS — AI Operating System for Claude Cowork

Build your personal AI Operating System inside Claude Cowork. One install. ~2 hours. Pays back every weekday morning, forever.

Stop using Claude like a chatbot. Start using it like infrastructure.

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Cowork AI OS is an open-source plugin that turns Claude Cowork into a configured AI teammate that knows your business, your voice, and your day. Built by Nuno Tavares for VCI cohort students and anyone who wants to install AI infrastructure instead of bouncing between chat tabs.

New in v0.10: Discovery layer. /browse-skills recommends community plugins for your business. /browse-connectors recommends MCP connectors to fill the gaps in your 7-bucket setup. Both read your about-me/business-brain.md and return ranked picks with reasoning + install instructions. Plus /onboard Phases 5 + 7 now invoke the recommenders to personalize your setup from day one. See the architecture brief and the v0.10 rollout post.

From v0.9 (still live): Progressive-disclosure architecture. Per-prompt "Start Up" latency under 3s. Auto-archiving memory. /optimize available any time Cowork feels slow.

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Quick links

Section	Who it's for
What you get	Everyone — what Cowork AI OS actually installs
⚠️ Mac users — read this first	Mac users (git prereq + known Mac issues)
⚠️ Windows users — read this first	Windows users (git prereq)
Install	The 4-step install
🍎 Mac install (recommended): zip upload	Recommended path for all Mac users
The 9 phases	Time budget for onboarding
Troubleshooting	When things go sideways

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What you get

• A claude.md handbook Claude reads on every session
• Four identity files describing who you are, what you sell, how you write, and what you've decided
• Gmail + Calendar wired with safe permissions
• A clean folder system Claude routes outputs to automatically
• Built-in skills enabled and a custom voice-tuned skill
• A daily brief firing every weekday morning
• Three recurring upkeep events so the system doesn't drift

All built through 9 guided phases. Pause-friendly. Sample-first. Resumable across sessions.

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⚠️ Mac users — read this first

Use the zip install — it's the recommended path on Mac. Anthropic has open bugs affecting marketplace-based plugin installs in Cowork on macOS (#26951, #28125). The zip upload bypasses all of them and is confirmed working in #39400. The marketplace command in Step 3 below is documented as the secondary path — try it if you prefer, but if anything fails, jump to the zip path.

Before installing, open Terminal (Spotlight → "Terminal" → Enter) and run:

git --version

If you see a version number like git version 2.43.0 → you're good. Skip to the install below.

If you see "command not found" → install git first:

xcode-select --install

Click Install in the popup. Wait ~5 minutes for the download. Then come back here.

Note: macOS does not use "Git Bash" — that's Windows-only. You only need the underlying git tool, which xcode-select --install provides.

After installing git, fully quit Claude Desktop (⌘+Q — closing the window isn't enough) and relaunch before retrying the install.

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⚠️ Windows users — read this first

Open PowerShell (Start menu → "PowerShell" → Enter) and run:

git --version

If you see a version number → you're good. Skip to the install.

If you see an error → download Git for Windows from git-scm.com/download/win, run the installer, accept all defaults. This package includes both git and Git Bash.

After installing, fully quit Claude Desktop (right-click tray icon → Quit) and relaunch.

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Install

Prerequisites

• Mac or Windows with admin install rights
• Paid Claude account (Pro $20/mo minimum — free tier doesn't include Cowork)
• Google account (for Gmail + Calendar in Phase 5)
• ~2 hours uninterrupted (or split across 2–3 sittings — pause-friendly)
• git installed (see above)

Step 1 — Install Claude Desktop

Download from claude.com/download. Sign in to your paid account.

Confirm you see three tabs: Chat, Co-Work, Code. (No Co-Work tab? Update Claude Desktop.)

Step 2 — Create your workspace folder

Create a folder named exactly Claude Cowork in your home directory.

Important: NOT inside OneDrive, iCloud, Dropbox, or Google Drive. Cloud sync conflicts with Cowork.

In the Cowork tab, click Choose folder, select Claude Cowork, click Allow. Header should read Working in: Claude Cowork.

Step 3 — Install Cowork AI OS

Mac user? Skip to the zip install. It's the recommended path on Mac and works in ~30 seconds.

Windows (and Mac users who prefer the marketplace): in Claude Desktop, run:

/plugin marketplace add automatedmarketer/cowork-ai-os
/plugin install cowork-ai-os@cowork-ai-os

Step 4 — Start onboarding

Open a fresh Cowork task. Type:

start onboarding

The 9-phase walkthrough begins.

What /onboard enables for you (no manual setup required): Phase 7 toggles ON four built-in Cowork skills that the plugin depends on — Skill Creator (required: this is what /add-skill hands off to when you build custom skills), docx (Word documents), pptx (slide decks), and canvas-design (visual outputs). You don't need to install these separately. They ship with Cowork; /onboard just walks you through enabling them in Settings → Customize. Skill Creator in particular is the foundation for everything Cowork AI OS does to evolve with your business — make sure it stays toggled on.

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🍎 ✅ Mac install (recommended): zip upload

⚠️ Already tried installing this plugin before? Read this first.

Cowork has a known Mac quirk: if you've previously uploaded a plugin with the same name (even a failed or stale attempt), the next upload is silently rejected — no error toast, no log line, the new zip just doesn't replace the old one. This happens because Cowork sends overwrite=false on every upload and there's no UI affordance to override it.

Fix before you re-upload (30 seconds):

1. 🗑️ Open Claude Cowork → Settings → Customize → Plugins (or Skills, depending on Cowork version)
2. Find any existing entry for cowork-ai-os — including manually-repacked attempts or stale uploads
3. Remove / delete it (trash icon, "Uninstall", or "Remove")
4. 🔄 Quit Cowork fully → relaunch (clears the in-memory marketplace cache)
5. Proceed to the install steps below

If this is your first time installing this plugin, skip this section.

This is the recommended install path for all Mac users. It bypasses Anthropic's open Cowork-on-macOS bugs (🚧 #26951, 🚧 #28125) and works on every Cowork build that supports plugin uploads. Workaround confirmed by users in #39400.

⏱️ 5 steps, ~30 seconds

1. 📦 Download the latest cowork-ai-os.zip (or cowork-ai-os-v0.10.2.zip) from the Releases page → Assets (or your training portal). Don't extract it. Keep the file as a single .zip.

   ⚠️ Important: download the zip from the Releases page, NOT the green ❌ Download ZIP button at the top of the repo page. That button wraps the repo in an outer folder (cowork-ai-os-main/) which double-nests the plugin and breaks Cowork's validator.

2. ⚙️ Open Claude Desktop → click your name (top right) → Settings.
3. 🔌 Customize → Browse plugins → look for the option to upload a custom plugin file.

   💡 Menu wording varies slightly between Cowork versions — look for "Upload", "Custom plugin", or "From file".

4. 📤 Drag in the zip. Wait for confirmation.
5. 🚀 Open a fresh Cowork task → type start onboarding (skills load on session start, not retroactively).

That's it. No marketplace, no terminal, no SSH keys, no git --version requirement.

💡 Why this is the recommended Mac path: Anthropic closed #27196 ("All Anthropic plugins fail in Cowork on macOS") as not planned — they don't currently intend to fix the marketplace path on Mac. The zip-upload path is effectively the supported install method on macOS going forward.

🐛 Troubleshooting

Symptom	What to do
🤐 Upload appears to succeed but plugin doesn't update / still showing old version	You have a stale entry from a previous upload attempt. Remove the old entry first (see the "Already tried installing" callout at the top of this section). Cowork silently rejects same-name re-uploads.
🔍 Can't find "Upload" / "Custom plugin" option	Look for "From file" / "Local plugin" / "Add manually". If genuinely absent, your Cowork version is older than the upload feature — 🔄 quit, update Claude Desktop, relaunch.
📄 Upload rejects the file	Confirm the file extension is .zip (not .plugin). Re-download directly from the Releases page; don't rename.
🚫 Plugin uploads but start onboarding does nothing	Open a brand new Cowork task. Skills load on session start, not retroactively.
👻 Plugin disappears after restart	That's 🚧 #38429 — Anthropic-side persistence bug. 🔄 Re-upload the zip after restart.

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What's inside

cowork-ai-os/                    ← the plugin
├── .claude-plugin/
│   └── plugin.json              Plugin metadata + version
├── skills/
│   ├── onboard/                 The 9-phase install walkthrough
│   │   ├── phases/              9 phase files (Phase 1 → Phase 9)
│   │   ├── samples/             Example files (sample-first onboarding)
│   │   └── templates/           Templates the install writes for you
│   ├── audit/                   "check my system" — score on the 4 C's
│   ├── level-up/                "what should I improve" — one specific move
│   ├── tune-up/                 "weekly tune-up" — 5-gate self-improvement
│   ├── morning-brief/           Daily inbox + calendar brief
│   ├── voice-writer/            Drafts in your voice
│   ├── optimize/                "Cowork is slow" → diagnose + fix (v0.9 migration + evergreen speed tool)
│   ├── browse-skills/           "what skills should I install" → 3 ranked picks for your business (v0.10)
│   ├── browse-connectors/       "what connectors do I need" → recommend MCPs to fill bucket gaps (v0.10)
│   └── add-skill/               Hands off to Cowork's Skill Creator
├── CONNECTORS.md                Gmail + Calendar setup notes
├── LICENSE                      MIT
└── README.md                    Plugin-internal docs

.claude-plugin/marketplace.json  ← marketplace registration (repo root)

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The 9 phases

Phase	What it builds	Time
1	Handbook (claude.md)	~10 min
2	About-me file	~15 min
3	Business brain	~15 min
4	Voice + memory files	~20 min
5	Gmail + Calendar connectors	~15 min
6	Folder system	~5 min
7	Skills tour + plugin install	~20 min
8	Daily brief on a schedule	~15 min
9	Integrated verification + upkeep	~15 min

Total: ~2 hours. Pause anytime with pause onboarding. Resume with continue onboarding.

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Troubleshooting

"Failed to install plugin" red toast (Mac)

Use the zip install — it's the recommended Mac path anyway.

/plugin marketplace add says "not found" or "could not connect"

• On Mac: that's #28125 / #26951. Use the zip install.
• On Windows: confirm git is installed (git --version), fully quit Claude Desktop (Quit from tray), and relaunch.

Cowork doesn't recognize /plugin commands

Update Claude Desktop to the latest version. The plugin commands ship with Cowork — older builds don't have them.

Plugin installs but skills don't load

Open a fresh Cowork task — skills load on session start. If still failing, see #39274 (Anthropic-side issue).

Claude Desktop fails silently on Windows after a Malwarebytes / antivirus conflict

Known Anthropic-side bug, reported May 2026. Malwarebytes Real-Time Monitoring (and possibly other active antivirus tools) can conflict with Claude Desktop and set an internal flag that doesn't clear after the conflict is resolved. Symptom: Claude Desktop runs but fails silently — prompts go nowhere, no error message. Workaround:

1. Manually clear the Claude Desktop flag (close Claude Desktop fully via tray icon → Quit; restart).
2. If the issue persists, disable the conflicting AV's real-time monitoring, restart Claude Desktop, then re-enable.
3. The student who reported this resolved it by switching to Windows Defender only (removing Malwarebytes' real-time component).

A bug report has been sent to Anthropic. Track it on the cowork-ai-os GitHub issues — search for "Malwarebytes" or "silent fail."

Cowork feels slow on startup (>3s before any response)

Run /optimize inside Cowork. It diagnoses two common causes (legacy v0.8 handbook directive, memory file overflow), shows you what it'll fix, and waits for your "yes" before making changes. Has a rollback option. Should not be necessary on a fresh v0.9+ install — but if you're upgrading from v0.7 or v0.8, this is the right tool.

Install hangs at any phase

Type pause onboarding, close the task, open a fresh task, type continue onboarding. Cowork AI OS picks up where you left off — your about-me/, outputs/, and _aibos/state.md survive across sessions.

How do I update Cowork AI OS?

/plugin update cowork-ai-os

Your about-me/, outputs/, and _aibos/state.md survive — they live in your workspace, not in the plugin.

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Curriculum (for VCI cohort students)

The full Project 01 — Core Setup curriculum (Quick Start + 8 lessons + concept deck) is available to VCI cohort members at vcinc.ai. Each lesson maps 1:1 to a phase of this install.

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Built by

Nuno Tavares — tech coach, founder of Automated Marketer, Lovable AI Ambassador, GoHighLevel Multiple Award Winner. Trains 7-figure entrepreneurs on AI infrastructure.

• 📰 Newsletter: automatedmarketer.net
• 📺 YouTube: @AutomatedMarketer
• 🎓 VCI cohort: vcinc.ai

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Contributing

Issues and PRs welcome. If you hit a Mac install snag not covered in Troubleshooting, please open an issue with:

• Your Cowork / Claude Desktop version
• The exact error message (red toast text or terminal output)
• Whether the zip fallback worked

That's the fastest way to get a fix landed.

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License

MIT — fork it, edit it, make it your own. See LICENSE.

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Cowork AI OS is open source at github.com/automatedmarketer/cowork-ai-os Built for VCI cohort students and anyone who wants to stop using Claude like a chatbot — and start using it like infrastructure.