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GitHub Copilot "Error on conversation request": Causes and Fixes

GitHub Copilot Chat says "Error on conversation request"? What the message means, the causes in VS Code issues, and the fixes that actually work.

By Engineer Foodie Desk ✓ Sources checked Nov 9, 2026

7 min read

Error text and causes checked Nov 9, 2026 in Microsoft’s VS Code repo: #314336, #340073, #337673, #337464 and #324972. Network fixes checked Nov 9, 2026 in GitHub’s Copilot network troubleshooting docs. Every source is listed at the bottom. No affiliate links on this page (how we work).

The exact error: Copilot request failed. Error on conversation request.

In VS Code’s Copilot Chat, the full message looks like this (from #314336, verified Nov 9, 2026):

Sorry, your request failed. Please try again.

Copilot Request id: ...
GH Request Id: ...

Reason: Error on conversation request. Check the log for more details.

Short answer: “Error on conversation request” is a wrapper, not a diagnosis. It means the request from VS Code to the model didn’t complete, and the real reason sits one line deeper, in the Copilot Chat log. In the VS Code issues, that deeper reason has been a proxy rejecting the connection, an HTTP/2 network error, a server-side 500, and a machine running out of open files. Same headline, four different stories.

Even Microsoft’s team says so. On Nov 1, 2026, a VS Code team member replied on #314336 that the attached log “shows successful requests, but not the underlying error,” and asked for “the exception accompanying “Error on conversation request,"" plus the model, the chat mode, and “whether retrying or starting a new chat succeeds.” Nobody sent it, and the issue auto-closed on Nov 8, 2026. So the first fix is: read the log, because nobody can help you without it.

What the issues show causes it

1. A proxy that blocks the connection

#337673 (Sep 24, 2026) shows the log line ending like this:

AbortError: Proxy response (403) !== 200 when HTTP Tunneling ... : Error on conversation request

The setup was a custom model endpoint (bring-your-own-key) behind a corporate HTTP proxy. The proxy refused the CONNECT request, so Copilot Chat never reached the model. The reporter traced it to how the bundled networking library tunnels through proxies. It was closed as a duplicate on Oct 3, 2026.

2. Network or firewall errors mid-request

#337464 (Sep 23, 2026, VS Code 1.138.0 and 1.139.0) logged net::ERR_HTTP2_PROTOCOL_ERROR ... : Error on conversation request, and the chat said: “Please check your firewall rules and network connection then try again.” The reporter saw it mostly on a custom endpoint and “less frequently” on Auto routed to GPT 5.6-Luna, and wrote it “Seems to happen when the agent attempts tool calls.” It was closed as a duplicate of an older network issue.

3. “Too many open files” on your own machine

This one is my favorite, in the way a flat tire is your favorite. #340073, opened Oct 6, 2026 and still open on Nov 9, 2026, has this full string:

unhandlederror-An unexpected error occurred: {"type":"failed","reason":"Error on conversation request. Check the log for more details.","reasonDetail":"Cannot read package config ... : too many open files.","requestId":"..."}

Nothing to do with your network. The reasonDetail is file-descriptor exhaustion (EMFILE), and it fired on the next-edit-suggestions path, not chat. VS Code’s automated scan flagged it as new in Copilot Chat extension 0.68.0 (absent in 0.67.0), with the representative bucket at “207 users / 39,300 hits” on Windows. Sneakers had “Too many secrets.” Copilot Chat 0.68.0 had too many open files. Neither was what anyone was looking for.

4. Server-side 500s

The same issue points to a sibling, #324972: the same unhandled-error wrapper with "reason":"Server error: 500", described by the bot as a “Server-side 500 surfacing client-side as an unhandled rejection.” It’s open as of Nov 9, 2026. A 500 is GitHub’s side, so check githubstatus.com before you start changing settings.

What about quota or credits?

No GitHub or VS Code doc I found ties “Error on conversation request” to running out of AI credits, and none of the issues above do either. Running out has its own messages. Rate limits have their own message, and VS Code’s docs say to check the Copilot status dashboard for your allowance, noting that “A temporary rate limit is separate from your monthly allowance” (VS Code troubleshooting, verified Nov 3, 2026).

Fixes, in order

Every step here comes from GitHub’s docs, VS Code’s docs or the issues. No proxy-bypass tricks.

  1. Retry once, then start a new chat. The chat itself says “Please try again,” and the VS Code team asked whether “starting a new chat succeeds” (#314336). If a new chat works, it was a one-off.
  2. Check githubstatus.com. If Copilot is having an incident, nothing on your machine will fix it. That’s the #324972 family.
  3. Read the log. Run Developer: Set Log Level → Trace, reproduce, then open the GitHub Copilot Chat output channel (VS Code docs, verified Nov 3, 2026). Look at the line that ends in Error on conversation request. The text before it is your real error: Proxy response (403), ERR_HTTP2_PROTOCOL_ERROR, Server error: 500 or too many open files.
  4. Test the connection the way GitHub suggests. From a terminal, run curl --verbose https://api.githubcopilot.com/_ping (the Copilot Chat endpoint; an HTTP 200 means you can reach it). Behind a proxy, add -x http://YOUR-PROXY-URL:PORT -i -L (GitHub network docs, verified Nov 9, 2026).
  5. Fix the proxy setup, with IT if needed. GitHub’s docs say a proxy URL starting with https:// “is not currently supported,” that Copilot supports basic or Kerberos proxy auth, and that company proxies must also be configured at the company level. Your network has to allow the Copilot hosts in GitHub’s allowlist reference (verified Nov 3, 2026), such as *.individual.githubcopilot.com.
  6. Certificate errors? Install the cert properly. For “unable to verify the first certificate”-type errors, GitHub says to install the custom certificates in your OS trust store. Turning off strict SSL is listed too, with the warning that it “can cause security issues and is not recommended.”
  7. Run the built-in diagnostics. GitHub Copilot: Chat Diagnostics shows which network checks fail, so you can compare them with your firewall, proxy or VPN setup (VS Code docs, verified Nov 3, 2026).
  8. Update VS Code and Copilot Chat. Run Code: Check for Updates. The too many open files bucket appeared new in extension 0.68.0, and #340073 is still open with no fix version posted as of Nov 9, 2026, so watch that issue.

Error on conversation request vs the other Copilot errors

MessageMeaningFix
Error on conversation requestRequest didn’t finishRead the log line
Language model unavailableNo model loadedNetwork, account
Exceeded your rate limitsToo many requestsWait, then retry

For the other two, see Copilot language model unavailable and GitHub Copilot rate limits.

Here’s what I’d do

I haven’t hit this error myself. This is a read of the issues and docs above. When it shows up, I retry once and open a new chat. If it comes back, I check githubstatus.com and then go straight to the Copilot Chat log, because the text before “Error on conversation request” tells you which of the four problems you’ve got. Scrolling that log can feel like The Shining (“All work and no play makes Jack a dull boy,” for pages), but the one line you need is in there.

On a work laptop, I’d assume proxy first and run the _ping curl before anything else. That gives IT something concrete to work with, instead of “Copilot’s broken.” On a personal machine with a clean network, I’d suspect a server-side blip or the 0.68.0 open-files bug and update.

If you’re on Copilot Free and wondering whether the limits are behind it, they aren’t documented as a cause. But GitHub Copilot free limits explains what Free actually caps. And if Copilot keeps failing on your network no matter what, GitHub Copilot alternatives and AI coding tools compared are where I’d look next.

FAQ

What does Error on conversation request mean in Copilot? It means Copilot Chat’s request to the model didn’t complete; the real cause is the error logged just before it in the GitHub Copilot Chat output channel.

Is GitHub Copilot down when I see Error on conversation request? Sometimes, since VS Code issue #324972 shows server-side 500s behind the same wrapper, so check githubstatus.com before changing settings.

Does a proxy cause Copilot Error on conversation request? It can; VS Code issue #337673 logged “Proxy response (403) !== 200 when HTTP Tunneling” ending in “Error on conversation request” when a corporate proxy rejected the connection.

What does too many open files mean in this Copilot error? Issue #340073 shows the reasonDetail “too many open files” on the next-edit-suggestions path, flagged as new in Copilot Chat extension 0.68.0 and open as of Nov 9, 2026.

Is Error on conversation request caused by running out of credits? Not documented; GitHub and VS Code docs don’t list it as an out-of-credits message, and rate limits show a separate “exceeded your rate limits” error.

Sources

  1. Microsoft VS Code GitHub issue #314336, “Copilot request failed. Error on conversation request.”: https://github.com/microsoft/vscode/issues/314336 (verified 2026-11-09)
  2. Microsoft VS Code GitHub issue #340073, unhandled error “Error on conversation request” with “too many open files”: https://github.com/microsoft/vscode/issues/340073 (verified 2026-11-09)
  3. Microsoft VS Code GitHub issue #337673, “Copilot Chat fails when an HTTP proxy rejects CONNECT for a custom HTTP endpoint”: https://github.com/microsoft/vscode/issues/337673 (verified 2026-11-09)
  4. Microsoft VS Code GitHub issue #337464, “Error: net::ERR_HTTP2_PROTOCOL_ERROR in Copilot chat”: https://github.com/microsoft/vscode/issues/337464 (verified 2026-11-09)
  5. Microsoft VS Code GitHub issue #324972, unhandled error “Server error: 500”: https://github.com/microsoft/vscode/issues/324972 (verified 2026-11-09)
  6. GitHub Docs, Troubleshooting network errors for GitHub Copilot: https://docs.github.com/en/copilot/how-tos/troubleshoot-copilot/troubleshoot-network-errors (verified 2026-11-09)
  7. GitHub Docs, Copilot allowlist reference: https://docs.github.com/en/copilot/reference/copilot-allowlist-reference (verified 2026-11-03)
  8. VS Code docs, Troubleshoot AI in Visual Studio Code: https://code.visualstudio.com/docs/copilot/troubleshooting (verified 2026-11-03)
  9. GitHub status page: https://www.githubstatus.com (checked 2026-11-03)

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