Agents Window: Failed to sign in to GitHub. Would you like to try again?

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Finding
This was not a real GitHub sign-out. The Agents Window’s local extension host failed to initialize properly, so VS Code never registered the built-in GitHub authentication provider. The UI translated that internal startup failure into the misleading sign-in popup.

Sequence
08:49:46: Agents Window starts its extension host.
08:50:50: VS Code reports: “The local extension host took longer than 60s to send its ready message” in renderer.log.
Authentication requests then repeatedly fail with:
Timed out waiting for authentication provider 'github' to register
Unknown extension GitHub.copilot-chat
No authentication provider host delegate found
09:05:16: The sign-in action fails with that timeout, producing the popup shown in your screenshot. The stack is in renderer.log.
09:05:17: Insiders restarts to apply an update, according to main.log.
On the clean launch, vscode.github-authentication activates normally in exthost.log.
GitHub authentication then succeeds repeatedly, including at 09:09 and 09:47, in renderer.log.
The update moved Insiders from commit 1d01c8df715905edfad1c49935680e8156358021 to 7debcd0e2acdea1c52de81bf9ee1620444407dda. The update overlapped the extension-host problem and may have contributed, but the logs don’t prove causation.

VS Code’s authentication service waits five seconds after extension activation for the provider to register, then throws the exact timeout seen here.

Verdict: a transient extension-host startup/update race, with a misleading auth error. There’s no evidence your GitHub credentials were revoked or that you were genuinely signed out. If it repeats on the newer build, restarting Insiders is the appropriate workaround and the 60-second extension-host readiness failure is the useful detail for a VS Code bug report.