Support request — Claude in Chrome cannot connect to Cowork sessions; no way to start a non-cloud task

Account: [lm@maciasspecialty.com](mailto:lm@maciasspecialty.com) (personal org, Claude Pro) Platform: Windows, Claude desktop app v1.40609.0 (Electron 42.10.0) Device name: macias-lonmar Date: September 1, 2026
Summary
The Claude in Chrome extension will not connect to my Cowork sessions. Every browser tool call returns "Browser extension is not connected." My desktop settings say browser use is unavailable in cloud sessions — but I can find no way to start a task that isn't a cloud session, so the capability appears unreachable on my build.
What I expected
Claude drives tabs in my own Chrome — the way it did when I first installed the extension. This matters because the built-in browser pane cannot print, and printing is the point of my workflow (filling and printing DOL WH-347 certified payroll forms weekly).
What actually happens
Any claude-in-chrome tool call returns: "Browser extension is not connected. Please ensure the Claude browser extension is installed and running... you may need to restart Chrome."
Occasionally instead: "the Chrome extension disconnected mid-operation."
Settings → General → Browser use shows: "Not available in cloud Code sessions, which don't run on this computer."
Connected browsers shows: "No browsers connected — Open Chrome with the Claude extension and sign in." (Chrome is open, extension installed, signed in.)
The extension's own starter prompts / demo challenges on its welcome page also do not run.
Timeline
Extension installed some time ago; it worked — Claude opened and controlled real Chrome tabs.
It stopped working mid-session, with no change on my end that I'm aware of.
Removed and reinstalled the extension from claude.ai/chrome.
On reinstall I was shown an organization picker listing MaciasSpecialty PM (this org has since been cancelled) and [lm@maciasspecialty.com](mailto:lm@maciasspecialty.com)'s Organization. I selected the personal org, which matches the account my sessions run under.
Restarted Chrome. Still not connected.
Started a brand-new task and explicitly asked it to use the Chrome extension rather than the built-in browser pane — same "not connected" error.
Approved sites list is empty ("No sites have been approved yet") and I have no way to add one, since no connection is ever established to trigger a permission prompt.
The contradiction I'd like resolved
My settings panel states browser use is not available in cloud sessions.
The documentation (Get started with Claude Cowork) states that Cowork runs tasks in the cloud, and that if a task needs "local files, browser use, and computer use," I should keep the desktop app open so Claude can reach them. My desktop app is open.
I can find no selector anywhere in the new-task flow to choose local execution over cloud.

So either browser use should work in a Cowork cloud session with the desktop app open (and it doesn't), or there's a way to start a local session that isn't exposed in my build. Which is it?
Possibly related: outbound proxy blocks
While troubleshooting, requests to dol.gov returned 403 CONNECT tunnel failed from both the cloud container and the shell on my own machine. If an egress allowlist on my account is also blocking bridge.claudeusercontent.com, that could be a contributing factor — flagging it in case it's relevant.
What I'm asking
Is Claude in Chrome supported in Cowork sessions on a Pro plan? If yes, what makes the connection work?
If it requires a local (non-cloud) session, how do I start one from the desktop app?
Did the cancellation of the MaciasSpecialty PM organization affect the extension's pairing, and if so how do I clear it?

Happy to provide screenshots of the settings panel, the org picker, and the extension welcome page on request.