Claude Cowork Reference Guide
Your complete quick-reference for mastering Claude Cowork—Anthropic's agentic desktop assistant for knowledge workers.
Quick Start Cheatsheet
Prerequisites
| Requirement | Details |
|---|
| Subscription | Pro ($20/mo) or Max ($100-200/mo) |
| Platform | macOS only (Windows planned, no ETA) |
| App | Claude Desktop (latest version) |
| Enable | Settings → Features → Enable Cowork |
Initial Setup
# 1. Create dedicated workspace
mkdir -p ~/Cowork-Workspace/{input,output}
# 2. Enable Cowork in Claude Desktop → Settings → Features
# 3. Grant folder access when prompted (ONLY ~/Cowork-Workspace)
Essential Prompt Pattern
Every Cowork request should follow this structure:
Task: [clear single objective]
Input: ~/Cowork-Workspace/input/
Output: ~/Cowork-Workspace/output/[filename.ext]
Format: [specific format requirements]
Model Selection
| Model | Best For | Speed |
|---|
| Sonnet | Daily tasks (emails, file organization) | Fast ⚡ |
| Opus | Complex analysis, multi-document synthesis | Slower 🐢 |
Rule of thumb: Start with Sonnet. Switch to Opus only if results lack depth.
Capabilities Matrix
What Cowork CAN Do
| Capability | Examples |
|---|
| Read/Write Files | Any file in granted folders |
| Create Office Docs | Word (.docx), Excel (.xlsx), PowerPoint (.pptx) |
| Generate PDFs | From any content |
| Extract Data (OCR) | Receipts, screenshots, scanned documents |
| Organize Folders | Rename, move, categorize files |
| Web Research | Via Chrome integration |
| Create Data Files | CSV, JSON, Markdown, HTML |
What Cowork CANNOT Do
| Limitation | Alternative |
|---|
| Execute code or scripts | Use Claude Code |
| Make API calls | Use Claude Code |
| Access cloud storage | Download files locally first |
| Process audio/video | Use specialized tools |
| Decrypt encrypted files | Decrypt manually first |
| Run on Windows/Linux | Use Claude Code |
Claude Products Comparison
When to Use Each Product
| If You Need... | Use This |
|---|
| Software development | Claude Code |
| File organization (no coding) | Cowork |
| Document creation (Word, Excel) | Cowork |
| Data extraction from images | Cowork |
| Running tests or scripts | Claude Code |
| Quick Q&A about files | Projects |
| Mobile access | Projects (web) |
Usage Limits & Tokens
Quota System
| Tier | Intensive Use | Reset Interval |
|---|
| Pro | ~1-1.5 hours | Every 5 hours |
| Max | 5x-20x more | Every 5 hours |
Token Budget by Task Type
| Task Type | Typical Tokens | Pro Sessions/Reset |
|---|
| Simple Q&A | 5K-10K | Many |
| File inventory | 20K-30K | 6-8 |
| Small file org (10-20 files) | 30K-50K | 3-5 |
| Large file org (50+ files) | 80K-150K | 1-2 |
| Multi-doc synthesis | 50K-100K | 2-3 |
| OCR batch (10+ receipts) | 60K-100K | 2-3 |
Context Limits
| Content Type | Approximate Capacity |
|---|
| Text pages | 150-500 pages |
| Documents | 50-100 docs |
| Images (OCR) | 50-100 images |
Hit the limit? Break tasks into smaller batches.
Output Formats
| Format | Extension | Capabilities |
|---|
| Word | .docx | Headers, tables, formatting, styles |
| Excel | .xlsx | Formulas, multiple sheets, charts |
| PowerPoint | .pptx | Slides, basic formatting |
| PDF | .pdf | Generated from any content |
| Text | .txt, .md | Plain text, Markdown |
| Data | .csv, .json | Structured data export |
| Web | .html | Basic web pages |
Regional Excel Settings
| Region | Formula Syntax | Example |
|---|
| US/UK | Comma separator | =SUM(A1,A2) |
| EU | Semicolon separator | =SUM(A1;A2) |
Always specify in your prompt: "Use European/US formula syntax"
Security Best Practices
Critical Rules (🔴)
| Rule | Why |
|---|
| Use dedicated workspace only | Limits potential damage |
| Never grant access to ~/Documents or ~/Desktop | Too broad, too risky |
| No credentials in workspace | Cowork can read everything |
| Verify file sources | Prompt injection risk |
High Priority Rules (🟠)
| Rule | Why |
|---|
| Review every execution plan | Catch mistakes before they happen |
| Backup before destructive operations | No undo button |
| Manage Chrome permissions carefully | Browser access is powerful |
Dangerous Patterns to Avoid
❌ "Process all files in ~/"
❌ "You have access to Documents"
❌ "Here's my password file"
❌ "Delete all duplicates" (without backup)
❌ Skip plan review
Common Issues & Quick Fixes
| Issue | Solution |
|---|
| Can't see Cowork option | Update Claude Desktop + restart |
| Permission denied | System Preferences → Privacy → re-grant folder access |
| Task stops mid-way | Break into smaller batches |
| Excel formulas show as text | Specify regional syntax in prompt |
| Chrome not working | Grant Accessibility permission |
| VPN conflicts | Disconnect VPN or use split tunneling |
| Computer sleep interrupts | Disable sleep during long tasks |
VPN Warning
VPN software creates routing conflicts with Cowork's internal VM. This is the #1 reported issue.
Error message: Failed to start Claude's workspace — VM connection timeout after 60 seconds
Solutions:
- →Disconnect VPN completely before using Cowork
- →Use split tunneling to exclude Claude Desktop
- →Batch Cowork tasks when VPN is off
Frequently Asked Questions
Getting Started
Capabilities
Security
Troubleshooting
Glossary
A
| Term | Definition |
|---|
| Agentic | AI systems that autonomously plan and execute multi-step tasks with minimal human intervention |
| Approval Gate | Checkpoint where Cowork shows planned actions and waits for confirmation |
| Artifact | A file created by Claude during a session (document, spreadsheet, etc.) |
C
| Term | Definition |
|---|
| Claude Code | Anthropic's CLI tool for developers with full shell access |
| Claude Desktop | The macOS application that hosts Cowork |
| Context Limit | Maximum text/data Claude can process (~200K tokens) |
| Context Window | The "memory" space holding your conversation and file contents |
| Cowork | Claude's agentic desktop feature for knowledge workers |
E-F
| Term | Definition |
|---|
| Execution Plan | Detailed list of actions Cowork proposes before execution |
| Extended Thinking | Claude's step-by-step reasoning capability |
| Folder Sandbox | Restricted area where Cowork operates (only granted folders) |
K-O
| Term | Definition |
|---|
| Knowledge Worker | Non-technical professionals working with information (PMs, analysts, writers) |
| Max Tier | Highest subscription ($100-200/mo) with 5x-20x usage |
| OCR | Optical Character Recognition—extracting text from images |
| Orchestrator | Main Cowork agent that creates plans and coordinates sub-agents |
P-S
| Term | Definition |
|---|
| Pro Tier | Standard subscription ($20/mo) with basic Cowork access |
| Prompt Injection | Security attack via malicious instructions hidden in files |
| Projects | Claude's web conversation interface with document upload |
| Research Preview | Early-access features not production-ready (expect bugs) |
| Sub-Agent | Specialized workers spawned for specific task parts |
T-W
| Term | Definition |
|---|
| Token | Text measurement unit (~4 characters or 0.75 words) |
| Workflow | Repeatable action sequence: input → process → output |
| Workspace | Dedicated folder structure for Cowork (~/Cowork-Workspace/) |
Workflow Cycle
Request → Analysis → Plan → ⚠️ REVIEW → Approve → Execute → Verify
↑
READ THIS CAREFULLY
Always review the execution plan before approving. This is your last chance to catch mistakes.
Summary
| If You Are... | Use |
|---|
| A developer needing code execution | Claude Code |
| A knowledge worker (non-technical) | Cowork |
| Just chatting/analyzing documents | Projects |
| On a budget | Projects |
| On Windows/Linux | Claude Code or Projects |
| Need file creation (Word, Excel) | Cowork |
| Need batch file processing | Cowork |
