Unable to use Cursor Chat – "An unexpected error occurred"

Where does the bug appear (feature/product)?

Bugbot / Security Review Agent

Describe the Bug

Situation

I can launch Cursor normally.
However, any prompt submitted in Chat returns an error.
The web version also does not work properly; I cannot use prompts there either.
The issue appears to affect all chats.

Timeline

I am not certain whether it worked yesterday, but it was working until the day before yesterday.
The problem was first noticed yesterday.

Network

Yesterday: Connected through corporate VPN.
Today: Connected directly to the corporate network (without VPN), but the issue remains.

Troubleshooting already performed

Reinstalled Cursor yesterday.
Issue persists after reinstall.
Cursor launches normally, but Chat functionality is unavailable.

Version

Cursor Version: 3.10.20

Could you please check the logs associated with the Request ID and advise on the cause of the issue?

Thank you.

Hi @kenzoo Thank you for reaching out. and sorry for the trouble.

Looking into your account, I can see that your chat requests aren’t reaching our servers since the update, while other activity from your account is still getting through normally. That tells us this isn’t a sign-in or general connectivity problem, it’s specific to the connection chat uses. When only chat is affected, and it happens on both the desktop app and the web version, it almost always points to something on the network path between you and our servers breaking the streaming connection that chat relies on.

A few things that should help narrow it down:

  1. In Cursor, open Settings > Network > Run Diagnostics and note any checks that fail. This guide covers the most common network and proxy issues: Network, proxy, and remote connections | Cursor Docs

  2. Since you’re on a corporate network, please ask your IT team to allow *.cursor.sh and *.cursor.com through any proxy, firewall, or SSL/deep packet inspection. That kind of inspection is the most common reason chat works one day and then fails after a network or policy change, and it would explain why the web version is affected too. (full list of domains to allowlist is available in Cursor Settings → Network → Required Domains

If you can share the results of the Network Diagnostics run, I’ll take another look from there.

I had the same issue in our corporate network, after upgrading to version 3.10.20.
What helped in my case was to switch HTTP compatibility mode to HTTP/2 in the Cursor network settings.

Thank for sharing this!

Hello @kevinn
I have completed additional troubleshooting and would like to share the results.

Additional investigation

  • I reinstalled Cursor, but the issue persists.

  • I also tested an older Cursor version, and the same issue occurs.

  • The issue occurs on both the desktop application and the web version.

  • The issue occurs when connected via VPN, on the corporate network, and also when using a mobile hotspot with VPN disabled.

  • Other users in the same organization are able to use Cursor normally.

  • Desktop Cursor launches successfully, but every chat request returns:

An unexpected error occurred. Request ID: e8c3cde7-94d2-4ecf-841c-78ccd71f073c

Network Diagnostics results

The following checks are successful:

  • DNS
  • Authentication
  • Authentication UI
  • Cursor Tab
  • Agent Endpoint
  • Codebase Indexing
  • Downloads
  • CDN

The following checks fail:

  • API
  • Ping
  • Chat
  • Agent

All failed checks report:

[internal] unable to get local issuer certificate

SSL Diagnostics reports:

Encrypted traffic is being intercepted by unrecognized certificate

Issuer:

O=Zscaler Inc.

CN=Zscaler Intermediate Root CA

The same result occurs even when using a mobile hotspot with VPN disconnected.

Given these findings, could you please advise whether Cursor recently changed any TLS or certificate validation behavior that might affect environments using Zscaler SSL inspection?

Also, since other users in the same company are able to use Cursor successfully, do you have any recommendations for identifying what difference on my machine could cause Cursor Chat traffic to fail while Authentication continues to work?

Thank you for your assistance.

I’m facing the exact same issue. pls let me know if you found the root cause or solution. @kevinn

Hi @kenzoo @Madhan_Santharaman I think I have a good solution for you.
Can you press Ctrl + Shift + P to Bring up the Command Palette and then type Open VS Code Settings.

Then search for Certificate and make sure the following two options are selected:

  • Http: System Certificates
  • Http: Experimental System Certificates V2.

That is the graphical way of modifying the settings, but if you prefer, you can also do it this way:
Using settings.json

  1. Press Ctrl+Shift+P.
  2. Run Preferences: Open User Settings (JSON).
  3. Add:
{

"http.systemCertificates": true,
"http.experimental.systemCertificatesV2": true

}

If other settings already exist, add these inside the existing {} with commas between entries.

  1. Save, fully quit Cursor, and reopen it.
  2. Rerun Network Diagnostics.

Both will have the same results.

If you’re still having an issue but you have colleagues that have everything working, please ask them to run Cursor Settings > Network > Run Diagnostics and check the SSL issuer:

  • If yours shows Zscaler but theirs shows Amazon RSA, your machines are receiving different SSL inspection policies. Please ask IT to align your policy or exempt Cursor domains from SSL inspection.
  • If both show Zscaler, but only your machine fails API, Ping, Chat, and Agent, please ask IT to compare the Windows Trusted Root and Intermediate Certification Authority stores and the Zscaler Client Connector policy on both machines.

The durable fix is for IT to exempt Cursor’s required domains from SSL inspection, not only to allow the traffic. The required domains are listed under Cursor Settings > Network > Required Domains and here:

After IT makes the change, fully restart Cursor and rerun Network Diagnostics.

Hello Cursor Support,

I accidentally created a second Cursor account on the same PC while setting things up. I never intended to use multiple free trials and only want to use my primary account. However, I’m now getting the error:

“Too many free trial accounts used on this machine.”

Request ID: 5ac0fda3-eb88-4015-a7de-ca4166d6fef5

Could you please review my account and let me know if my free trial can be restored?

Thank you.

Hi @VIPUL_THAKOR, Thank you for the post. Unfortunately, we are not able to override this security mechanism. I believe there is a cool down period so you may be unblocked in a couple of days.

Thank you for your response and for the clarification. I understand that you’re unable to override the security mechanism. I’ll wait for the cooldown period and try again in a couple of days. I appreciate your time and help!

@kevinn Thanks for the support. I’m stilling facing the same issue. even i downgraded my cursor desktop. As you mentioned i’ll check with IT team, i can see Zscaler in both my machine and y colleagues machine. but he has older versions of cursor desktop. between everything works for him.

Meanwhile, i have noticed one more thing i do have enterprise login and i’m in the members list and i can able see and login browsers but when i login via desktop it’s considering as free plan. any idea on this?