Critical Bug: AI Session Context Loss during Mandatory Updates

Support Bug Reports
1

Where does the bug appear (feature/product)?

Cursor IDE

Describe the Bug

Complete loss of AI session context and chat history after a mandatory system update.

  1. Start an active AI chat session.
  2. Wait for a mandatory update prompt.
  3. Apply the update and restart.
  4. Notice the chat history and context are completely los

Steps to Reproduce

  1. Start a chat with any AI model.
  2. Perform a mandatory system update when prompted.
  3. Restart the app and verify if the previous chat session is lost.

Expected Behavior

The application should persist active session context and chat history during updates, or at least prompt for a save/checkpoint before restarting

Operating System

Windows 10/11

Current Cursor Version (Menu → About Cursor → Copy)

Version: 2.3.26 (system setup)
VSCode Version: 1.105.1
Commit: bdbdd3f2cf698f583c5cdd2a6dc0f5aec4ed5f90
Date: 2026-01-07T07:11:15.842Z
Electron: 37.7.0
Chromium: 138.0.7204.251
Node.js: 22.20.0
V8: 13.8.258.32-electron.0
OS: Windows_NT x64 10.0.26200

For AI issues: which model did you use?

Gemini 1.5 Pro

For AI issues: add Request ID with privacy disabled

Not available due to complete session loss

Additional Information

The application should persist active session context and chat history during updates, or at least prompt for a save/checkpoint before restarting

Does this stop you from using Cursor

No - Cursor works, but with this issue

2

Hey there.

I think this is super good feedback. I’ll flag this for attention!

3

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