Claude is one of the strongest assistants around, and Cowork is where it takes on longer jobs. As of 6 October 2026, those jobs run in Anthropic’s cloud, which is the clearest difference from Henchman.
Cowork is Claude at work in the cloud
Cowork handles research, analysis, documents and other multi-step tasks. It works in folders you connect, uses connectors and its own browser, and can control your apps with permission. New tasks on Pro and Max plans run on Anthropic’s servers, so they keep going with your laptop closed, and scheduled tasks don’t need your computer at all. Claude has a free plan, and Cowork comes with the paid ones.
Henchman keeps the thinking on your Mac
Henchman is a free Mac app with no account. The thinking happens on your Mac with open models you add, so your prompts, memory and files don’t go to a model company. You hire a crew of henchmen with personalities, give them routines like a morning brief, and text them from Telegram, Discord or Slack direct messages while your Mac is awake.
Which one fits
If you want the strongest reasoning and don’t mind the cloud, Claude is the better tool. If you want a private crew that costs nothing and lives on your Mac, choose Henchman.