Server error - The server failed 4 times

Support Help
1

Where does the bug appear (feature/product)?

Somewhere else…

Describe the Bug

Request ID: 685b9923-150b-4d0b-a96e-493092a6887b
The server failed 4 times. Please try again, or contact support if the issue persists.
[internal] self signed certificate in certificate chain
RetriableError: [internal] self signed certificate in certificate chain
at RQk (vscode-file://vscode-app/Applications/Cursor.app/Contents/Resources/app/out/vs/workbench/workbench.glass.main.js:9737:128291)
at eBl._executeTurn (vscode-file://vscode-app/Applications/Cursor.app/Contents/Resources/app/out/vs/workbench/workbench.glass.main.js:9737:150319)
at async eBl.executeTurn (vscode-file://vscode-app/Applications/Cursor.app/Contents/Resources/app/out/vs/workbench/workbench.glass.main.js:9737:138594)
at async F1e.runAgentLoop (vscode-file://vscode-app/Applications/Cursor.app/Contents/Resources/app/out/vs/workbench/workbench.glass.main.js:9732:17076)
at async Zmu.streamFromAgentBackend (vscode-file://vscode-app/Applications/Cursor.app/Contents/Resources/app/out/vs/workbench/workbench.glass.main.js:23563:24525)
at async Zmu.getAgentStreamResponse (vscode-file://vscode-app/Applications/Cursor.app/Contents/Resources/app/out/vs/workbench/workbench.glass.main.js:23563:49848)
at async e8e._submitChatMaybeAbortCurrent (vscode-file://vscode-app/Applications/Cursor.app/Contents/Resources/app/out/vs/workbench/workbench.glass.main.js:9715:5198)
at async e8e.submitChatMaybeAbortCurrent (vscode-file://vscode-app/Applications/Cursor.app/Contents/Resources/app/out/vs/workbench/workbench.glass.main.js:9710:90743)

Steps to Reproduce

Send a message

Screenshots / Screen Recordings

Screenshot 2026-10-28 at 15.07.30.png
Screenshot 2026-10-28 at 15.07.30.png1260×494 30 KB

Operating System

MacOS

Version Information

Version: 3.27.22
VS Code Extension API: 1.128.0
Commit: b1aa50cb6db84fd3e8c808259cb172ea73425c10
Date: 2026-10-27T00:33:02.045Z
Layout: Agent Window
Build Type: Stable
Release Track: Default
Electron: 42.11.16
Chromium: 148.0.7778.280
Node.js: 24.19.0
V8: 14.8.178.38-electron.0
xterm.js: 6.1.0-beta.291
OS: Darwin arm64 25.6.0

Does this stop you from using Cursor

Yes - Cursor is unusable

6

Hey @Guilherme_Behling,

That error means something on your network (usually a company VPN or security gateway) is re-signing HTTPS traffic with a certificate Cursor doesn’t trust, so the request is blocked before it leaves your Mac. It isn’t a problem with your account or the app itself, and it looks like your chats are going through again already.

To make it stick, do this in Cursor (the IDE):

  1. Press Cmd+Shift+P, type “Preferences: Open User Settings (JSON)” and open it.

  2. Add these two lines inside the outer braces:

    "http.experimental.systemCertificatesV2": true,
"cursor.general.disableHttp2": true

  3. Fully quit Cursor with Cmd+Q and reopen it.

  4. Make sure your company’s root certificate is in Keychain Access and set to Always Trust.

If it still fails, open Cursor Settings → Network → Network Diagnostics, run it, and paste the output here (the SSL line names the certificate that is intercepting the connection). A quick check: if it works on a phone hotspot, the interception is on your work network, and your IT team will need to exclude Cursor’s domains from SSL inspection. The list is here: Network Configuration | Cursor Docs

8

Hi @Colin. Thanks for the help!

I followed the steps and it’s working again now. Really appreciate it!