> real trade-off … thankful for any feedback

Speaking as a tiny but regulated SMB that's dabbling in skill plugins with Cowork: we strongly appreciate and support this stance. We hope you don't relax your standards, and need you not to. We strongly agree with (1), (2), and (3).

If working outside the sandbox becomes available, Cowork becomes a more interesting exfil vector. A vbox should also be able to be made non-optional — even if MDM allows users to elevate privileges.

We've noticed you're making other interesting infosec tradeoffs too. Your M365 connector aggressively avoids enumeration, which we figured was intentional as a seatbelt for keeping looky-loos in their lane.* Caring about foot-guns goes a long way in giving a sense of you being responsible. Makes it feel less irresponsible to wade in.

In the 'thankful for feedback' spirit, here's a concrete UX gap: we agree approval fatigue matters, and we appreciate your team working to minimize prompts.

But the converse is, when a user rejects a prompt — or it ends up behind a window — there's no clear way to re-trigger. Claude app can silently fail or run forever when it can't spin up the workspace, wasn't allowed to install Python, or was told it can't read M365 data.

Employees who've paid attention to their cyber training (reasonably!) click "No" and then they're stuck without diagnostics or breadcrumbs.

For a CLI example of this done well, see `m365-cli`'s `auth` and `doctor` commands. The tool supports both interactive and script modes through config (backed by a setup wizard):

https://pnp.github.io/cli-microsoft365/cmd/cli/cli-doctor/

Similarly, first party MCPs may run but be invisible to Cowork. Show it its own logs and it says "OK, yes, that works but I still can't see it, maybe just copy and paste your context for now." A doctor tool could send the user to a help page or tell them how to reinstall.

Minimal diagnostics for managed machines — running without local admin but able to be elevated if needed — would go a long way for the SMBs that want to deploy this responsibly.

Maybe a resync perms button or Settings or Help Menu item that calls cowork's own doctor cli when invoked?

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* When given IDs, the connector can read anything the user can anyway. We're able to do everything we need, just had to ship ID signposts in our skill plugin that taps your connector. Preferred that hack over a third party MCP or CLI, thanks to the responsibility you look to be iteratively improving.

Anthropic Cowork feature creates 10GB VM bundle on macOS without warning