Connection error in one chat window but works in another

Bug Reports
1

Where does the bug appear (feature/product)?

Cursor IDE

Describe the Bug

Some chat instances fail with SSL/TLS handshake errors while others work fine in the same workspace.

Error Details:

Request ID: 555b5388-fa66-4037-be09-b9baea90bed2
ConnectError: [internal] 1288492638272:error:10000410:SSL routines:OPENSSL_internal:SSLV3_ALERT_HANDSHAKE_FAILURE:../../third_party/boringssl/src/ssl/tls_record.cc:486:SSL alert number 40

    at UZc.$streamAiConnect (vscode-file://vscode-app/Applications/Cursor.app/Contents/Resources/app/out/vs/workbench/workbench.desktop.main.js:6331:406060)
    at async vscode-file://vscode-app/Applications/Cursor.app/Contents/Resources/app/out/vs/workbench/workbench.desktop.main.js:565:75277
    at async Object.run (vscode-file://vscode-app/Applications/Cursor.app/Contents/Resources/app/out/vs/workbench/workbench.desktop.main.js:6399:42465)
    at async o (vscode-file://vscode-app/Applications/Cursor.app/Contents/Resources/app/out/vs/workbench/workbench.desktop.main.js:2815:1269)
    at async Promise.allSettled (index 0)
    at async o7r.run (vscode-file://vscode-app/Applications/Cursor.app/Contents/Resources/app/out/vs/workbench/workbench.desktop.main.js:2815:6513)

Symptoms:

  • Fresh chat windows fail immediately with “Connection Error” on first message
  • Error: “Connection failed. If the problem persists, please check your internet connection or VPN”
  • Some chat instances work fine while others consistently fail
  • Issue persists after clearing cache, reindexing workspace, closing/reopening chats, and restarting Cursor

Environment:

  • Subscription: Pro
  • Multiple chat windows in same workspace
  • Some chats work, others fail with same error

Additional Issue:
Rules are only processed on the first message of a chat. If a chat fails on first message, rules cannot be applied. If a working chat is continued, rules may not be applied to subsequent messages.

Steps to Reproduce

  1. Open Cursor with a workspace
  2. Open a new chat window
  3. Type first message in the new chat
  4. Connection error appears immediately
  5. Some chat windows work fine, others consistently fail with SSL handshake error
  6. Issue persists after clearing cache, reindexing, closing/reopening chats, and restarting Cursor

Expected Behavior

All chat windows in the same workspace should connect successfully. SSL handshake should complete without errors.

Screenshots / Screen Recordings

Screenshot 2025-12-02 at 04.08.55.png
Screenshot 2025-12-02 at 04.08.55.png649Ă—288 17.5 KB

Operating System

MacOS

Current Cursor Version (Menu → About Cursor → Copy)

Version: 2.1.39 (Universal)
VSCode Version: 1.105.1
Commit: 60d42bed27e5775c43ec0428d8c653c49e58e260
Date: 2025-11-27T02:30:49.286Z
Electron: 37.7.0
Chromium: 138.0.7204.251
Node.js: 22.20.0
V8: 13.8.258.32-electron.0
OS: Darwin arm64 24.3.0

For AI issues: which model did you use?

Auto
Likely Composer 1 but same for others

For AI issues: add Request ID with privacy disabled

Request ID: 555b5388-fa66-4037-be09-b9baea90bed2

Does this stop you from using Cursor

Sometimes - I can sometimes use Cursor

2

Hey, thanks for the report. Let’s check a few things, since SSLV3_ALERT_HANDSHAKE_FAILURE is often related to network/proxy issues:

  1. Disable HTTP/2
  • Settings Cmd+, → search for “HTTP/2” → enable “Disable HTTP/2”
  • Restart Cursor and check in a new chat
  1. Network diagnostics
  • Settings → Network → Run Diagnostics → send a screenshot/results
  1. VPN/proxy/corp network
  • Are you using VPN/Zscaler/proxy/antivirus with SSL inspection? Try without them or from another network
  1. Rule out extension interference
  • Run: cursor --disable-extensions
  • In the new window, try the chat
  1. Logs and Request ID for comparison
  • View → Output → select “Cursor” → logs at the time of the error
  • Help → Toggle Developer Tools → Console → screenshot of errors (and, if possible, Network tab for the first request)
  • Send 2-3 Request IDs from failed chats and 1 from a working one (chat menu → Copy Request ID)

Share the details - I’ll pass it to the team.

3
  1. Disable HTTP/2

  • Settings Cmd+, → search for “HTTP/2” → enable “Disable HTTP/2” - done

  • Restart Cursor and check in a new chat - done
    it seems working workaround but it is working on http/2 mostly

  1. Network diagnostics
4
  1. VPN/proxy/corp network
  • Are you using VPN/Zscaler/proxy/antivirus with SSL inspection? Try without them or from another network

i don’t have anything like this

5
  1. Logs and Request ID for comparison
6
7
  • Send 2-3 Request IDs from failed chats and 1 from a working one (chat menu → Copy Request ID)

Request ID: d1b34023-5adb-48ba-8500-4d3b6afbe4ef
Request ID: 341019eb-2619-4cdb-b5dc-32511e28d796
Request ID: 17353043-07c4-4ade-9be8-81df7a68299d
Working (HTTP/2): 87c835bb-30ef-4208-b225-148e3339311c

8

@deanrie any updates on this?

9

Hey, thanks for the update.

Please do:

  1. Update to 2.2.x via Help → Check for Updates or Download · Cursor
  2. Enable HTTP/2 and try a new chat
  3. If it still fails, please share:
    • 2–3 Request IDs from failing chats and 1 from a working one (after updating)
    • Screenshots of Settings → Network → Run Diagnostics
    • Console errors from Help → Toggle Developer Tools

Temporary workaround - Settings → search “HTTP/2” → enable “Disable HTTP/2”.
Let me know if the update helped.

1 Like