OAuth tokens not persisting - requires /login for each web handoff session

[natierau1]

Environment

• OS: macOS 15.6.1 (Sequoia)
• Claude Code Version: 2.1.4

Problem

OAuth tokens are not being persisted to disk. Each new terminal session requires running /login before the & (web handoff) feature works.

Expected Behavior

After authenticating once, the OAuth tokens should persist across terminal sessions, allowing & web handoff to work without re-authentication.

Actual Behavior

• ~/.claude.json contains oauthAccount with account metadata (email, org UUID, display name)
• No accessToken, refreshToken, or expiresAt fields are stored
• Must run /login in each new terminal session to use & web handoff
• After /login, web handoff works correctly for that session

Diagnostic Output

$ cat ~/.claude.json | python3 -c "import sys,json; d=json.load(sys.stdin); print(json.dumps(d.get('oauthAccount', {}), indent=2))"
{
  "accountUuid": "...",
  "emailAddress": "...",
  "organizationUuid": "...",
  "hasExtraUsageEnabled": false,
  "displayName": "...",
  "organizationRole": "admin",
  "workspaceRole": null,
  "organizationName": "..."
}

Note: No token fields present. Grep for token|accessToken|refreshToken|expires only returns API usage token counts, not OAuth credentials.

Additional Context

• ~/.config/claude-code/ directory does not exist
• No keychain entry found for "claude-code"
• autoUpdates is set to false in config

[github-actions]

Found 3 possible duplicate issues:

1. [BUG] macOS OAuth authentication succeeds but auth token not persisted - shows 'Missing API key' after successful login #5244
2. [BUG] v2.0.14 macOS Keychain issue - OAuth authentication doesn't persist without security unlock-keychain each session #9403
3. [BUG] Claude Pro authentication not persisting on Linux #5767

This issue will be automatically closed as a duplicate in 3 days.

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[natierau1]

Update: Clean Install Performed - Bug Confirmed

Performed a complete clean install to rule out conflicting installations. The bug persists.

What was found before cleanup:

• Two Claude Code installations: Native 2.1.4 + Homebrew 2.0.73
• Old CLI remnant: ~/Library/Application Support/claude-cli-nodejs (older, different tool)
• Multiple config locations

Cleanup steps performed:

1. Backed up ~/.claude/ (agents, settings, plugins, skills)
2. Removed Homebrew installation (brew uninstall --cask claude-code)
3. Removed native installation (~/.local/share/claude, ~/.local/bin/claude)
4. Removed old CLI (~/Library/Application Support/claude-cli-nodejs)
5. Deleted ~/.claude.json entirely
6. Cleaned ~/.claude/ cache/temp directories
7. Fresh install via curl -fsSL https://claude.ai/install.sh | sh
8. Restored user data (agents, settings)

Post-cleanup verification:

✓ Single claude binary: ~/.local/bin/claude
✓ Version: 2.1.4
✓ No Homebrew claude
✓ No old CLI remnants
✓ Fresh ~/.claude.json created

Result after clean install:

$ cat ~/.claude.json | python3 -c "import sys,json; d=json.load(sys.stdin); print(json.dumps(d.get('oauthAccount', {}), indent=2))"
{
  "accountUuid": "...",
  "emailAddress": "...",
  "organizationUuid": "...",
  "hasExtraUsageEnabled": false,
  "displayName": "...",
  "organizationRole": "admin",
  "workspaceRole": null,
  "organizationName": "..."
}

Still no accessToken, refreshToken, or expiresAt fields.

Conclusion

This confirms the bug is in Claude Code 2.1.4 itself - not caused by conflicting installations or stale config. OAuth tokens are simply not being written to disk.