github / github/app

Session creation shows generic "Failed to initialize workspace" when SAML SSO token expires

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Description

## Describe the bug
When an organization enforces SAML SSO and the OAuth token authorization lapses, creating a new session fails with `Session creation failed: Failed to initialize workspace`. The actual cause — a 403 with "you must re-authorize the OAuth Application" — is only visible in `~/.copilot/logs/`.

## Expected behavior
1. The UI should surface the SAML SSO error directly, ideally with a clickable re-authorization link
2. After re-authorizing on GitHub.com, the app should automatically detect the refreshed authorization and retry — not require a full app restart

## Steps to reproduce
1. Be a member of an org with enforced SAML SSO
2. Wait for SSO authorization to expire
3. Try to create a new session in a repo owned by that org
4. See generic "Failed to initialize workspace"

## Logs
```
fatal: unable to access '...': The requested URL returned error: 403
remote: The 'org' organization has enabled or enforced SAML SSO.
remote: To access this repository, you must re-authorize the OAuth Application 'GitHub'.
```

## Environment
- Windows, Copilot app v1.0.80

Contributor guide

Open the contributing guide

Research direction

Reproduce session creation on Windows with an organization enforcing SAML SSO, then inspect ~/.copilot/logs/ while tracing the desktop UI's new-session flow. Verify that the 403 and re-authorization link are surfaced, and that the refreshed authorization is detected so session creation retries without restarting the app.

Written by the indexing model from the issue text.

Assessment

Tech stack
github
Domain
authentication, authorization, desktop
Issue type
Bug
Difficulty
4/5
Estimated time
3-5 days
Activity status
Active
Clarity
Mostly clear
Newbie friendliness
52/100

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