Claude Cowork + Google Drive Connector Troubleshooting

Job description Claude Cowork + Google Drive connector: diagnose and fix a connection that will not persist I am an independent contractor running Claude on a Team workspace. I use Claude Cowork daily and need the Google Drive connector working reliably against our company Google Workspace. It is not. The problem The Google Drive connector appears in our Claude desktop app connector list with a Connect button. Clicking Connect launches the Google OAuth flow, we authorize, and the browser returns a Claude "Connected" confirmation page. The desktop app connector list still shows Connect, not a connected checkmark. The connector never appears as a toggle in the + menu inside a Cowork task, so Claude has no Drive tools available and cannot see the Drive at all. I have already tried: - Full quit and relaunch of the desktop app, not just closing the window - Reopening the Connectors settings panel to force a refresh - Confirming the connector shows as installed at the organization level Notably, this connection has worked before. I have had Drive connected and stable for days at a stretch in the past, then lost it. So this is a connection that degrades or fails to re-establish, not a first-time setup we have never gotten working. What I need Work with me over a screen share to identify root cause and restore a stable connection. We expect the answer is one of: a Claude account or workspace mismatch between the desktop app and the browser handling the OAuth redirect, a Google Workspace admin policy blocking or periodically revoking third party app authorization, an organization level connector permission in our Claude workspace, a token refresh or session expiry problem, or a desktop app version or cache issue. Scope 1. Live screen share session to reproduce and diagnose the failure 2. Identify the specific root cause with evidence, not a guess 3. Walk us through the fix while we drive, or tell us exactly what our Claude workspace admin and Google Workspace admin each need to change 4. Verify the connection works end to end: Claude can list and read files from our company Drive inside a Cowork task 5. Confirm persistence, meaning the connection survives an app restart and is still live the following day 6. A short written summary of root cause, the fix applied, and what to do if it recurs Access and security This touches our company Google Workspace and our Claude organization, so access is screen share only. You will not receive credentials, admin seats, or logins. We drive, you direct. Come prepared to work this way. If you believe you cannot diagnose it without direct access, say so in your proposal and explain what you would need and why, and we will evaluate separately. Environment - macOS, Claude desktop app - Claude Team workspace - Google Workspace (company domain, not personal Gmail) - Cowork used for document work and file organization Timeline We would like to start immediately and finish in one or two sessions. This is scoped as a short hourly engagement, roughly 2 to 5 hours. If you resolve it well there is a good chance of follow on work as we expand Claude across the company. Screening questions Please answer these directly in your proposal. Proposals that do not answer them will not be reviewed. 1. Have you specifically resolved a Claude connector OAuth failure before? Describe what the root cause turned out to be. 2. What are the top three causes you would check first for the symptom described, and in what order? 3. Which Google Workspace admin console settings can block or revoke a third party app's Drive access, and where are they found? 4. What is your availability this week for a 60 to 90 minute screen share, in US Pacific time? I'm looking forward to hearing from you! -Clif