Different categories, frequently confused
Cowork sits in a young category: desktop-native, file-first, local-execution AI agents. The two products people compare it to most are OpenAI Operator (web-task agent in a managed cloud browser) and ChatGPT Desktop with Custom GPTs (chat with file uploads). Each is genuinely good at something Cowork is not.
The five differences that change the choice: execution location (Cowork: your Mac; Operator: OpenAI cloud; ChatGPT Desktop: hybrid), file access (Cowork: real disk; Operator: none; Desktop: uploads only), parallel agents (Cowork yes, others no/limited), MCP ecosystem (Cowork hooks into 1,800+ servers, Operator has its own narrower integrations), remote control (Cowork has Dispatch, Operator has none).
Operator's wins: web automation benchmarks (87% WebVoyager vs Cowork's 56%), zero-install (subscribe, go), great for booking/ordering/form-filling on websites. Cowork's wins: anything that touches files, anything privacy-sensitive (local processing), anything with parallel decomposition.