[BUG] Cowork session context stuck at 6-week-old snapshot after credit exhaustion + plan upgrade + app update

Preflight Checklist

• [x] I have searched existing issues and this hasn't been reported yet
• [x] This is a single bug report (please file separate reports for different bugs)
• [x] I am using the latest version of Claude Code

What's Wrong?

Active Cowork session context reverts to a ~6-week-old snapshot every time the session is opened. The session was working normally as recently as April 11, 2026. After Claude Desktop auto-updated to the latest version, the session now loads with context frozen at approximately March 5, 2026 — the date I previously exhausted credits on my Pro plan.
Filesystem evidence confirms the issue: ~/Library/Application Support/Claude/claude-code-sessions/ has a last-modified date of March 5, 2026 at 9:49 PM, meaning no session data has been written to this directory since the credit exhaustion event. Meanwhile, claude-code/ and claude-code-vm/ are both modified today, confirming the app itself is running and active.
Since the credit exhaustion, I have both increased my credits and upgraded from Pro to the Max plan. The app recognizes the Max plan (model selection, features, etc.), but session persistence appears to have never resumed writing to claude-code-sessions/.

What Should Happen?

Session context should reflect all work completed since March 5, including work done as recently as April 11. Plan upgrades and credit replenishment should restore full session write functionality. At minimum, if session writes fail (e.g. due to credit exhaustion), the app should surface an error rather than silently freezing the session directory.

Error Messages/Logs

No error messages displayed in the UI. The session silently loads stale context with no warning or notification that it is outdated.

Steps to Reproduce

1. Use Cowork on a Pro plan until credits are exhausted (~March 5, 2026 in my case)
2. After credit exhaustion, increase credits and/or upgrade plan (I upgraded to Max)
3. Continue using the same Cowork session — it appeared to function normally
4. Allow Claude Desktop to auto-update to the latest version
5. Reopen the same Cowork session
6. Session context has reverted to the state it was in at the time of credit exhaustion
7. Verify by checking ~/Library/Application Support/Claude/claude-code-sessions/ — last modified date matches the credit exhaustion date, not recent activity

_Note: The session appeared to work between steps 2–4, suggesting context may have been held in memory but never persisted to disk after the credit event._

Claude Model

Opus

Is this a regression?

Yes, this worked in a previous version

Last Working Version

Session was functioning normally on April 11, 2026 (version prior to most recent auto-update)

Claude Code Version

Claude 1.1617.0 (8d6345) 2026-04-09T16:10:15.000Z

Platform

Anthropic API

Operating System

macOS

Terminal/Shell

Terminal.app (macOS)

Additional Information

Filesystem state from ~/Library/Application Support/Claude/:

claude-code-sessions/ — last modified March 5, 2026 at 9:49 PM (stale, matches credit exhaustion date)
IndexedDB/ — last modified March 13, 2026 (also stale)
claude-code/ — last modified today (active)
claude-code-vm/ — last modified today (active)
local-agent-mode-sessions/ — last modified Feb 18, 2026 (legacy, unused)

Related issues: #45076 (session history silently lost between sessions), #33130 (sessions disappearing after app updates). This issue differs in that the trigger appears to be a credit exhaustion event that froze the session write path, which was never resumed after plan upgrade.
Screenshots of filesystem attached.