"Failed to connect to GitHub. Please try again later."

[realnotsteve]

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Receiving this message whenever I try to connect chatGTP macOS app to GitHub. Other macOS apps are connected. There is no existing connection from chatGTP. Any ideas? Thanks.

[angelscatman]

This looks like an issue with the OAuth callback handshake or a stale token session.

You can try debugging it with these steps:

1. Clear Stale Tokens: Go to GitHub Settings > Applications > Authorized OAuth Apps. If you see "ChatGPT" listed there (even if the app says it's not connected), revoke it. This forces a clean re-authorization request.
2. Check the Callback Handler: Sometimes non-default browsers (like Arc or Brave) or extensions strip the callback parameters required for the connection. Try temporarily setting Safari as your default browser to rule this out.
3. Network Filters: If you use tools like Little Snitch, LuLu, or a strict VPN, ensure they aren't blocking the local connection request from the ChatGPT binary.

Hope this helps solve it.

[realnotsteve]

Thank you, so far no joy. I am baffled by there being literally no hits in google for that error message. How is that possible?

[Nixxx19]

@realnotsteve

It usually means the ChatGPT macOS app cannot complete the OAuth handshake with GitHub.
Since other macOS apps are connecting fine, the issue is most likely local to the ChatGPT app or its cached credentials.

Try these steps:

1. Fully quit the ChatGPT app

   • Menu bar → ChatGPT → Quit
   • Reopen and try connecting again.

2. Clear any partial or stale GitHub authorization

   • Go to macOS System Settings → Privacy & Security → Developer Tools
   • Remove ChatGPT if listed, then relaunch the app.

3. Check if GitHub registered a failed authorization attempt

   • Visit: https://github.com/settings/applications
   • Under Authorized OAuth Apps, remove any ChatGPT entry if it exists.
   • Retry connection from the ChatGPT app.

4. Verify network rules

   • VPN, firewall tools (like Littlesnitch / Radio Silence), or corporate networks can block OAuth redirects.
   • Temporarily disable them and try again.

5. Sign out & sign back into the ChatGPT app
   Sometimes the app stores a corrupted session token that breaks external integrations.

6. Reinstall the ChatGPT macOS app

   • Delete the app
   • Remove ~/Library/Application Support/ChatGPT
   • Reinstall the latest version.

If none of these work, collect the request ID shown in the error (if available) and open a support ticket with GitHub or OpenAI. The request ID allows their teams to inspect the failed OAuth transaction directly.

[realnotsteve]

Thank you, I did try but seem to still have the issue. I finally found something Google, but then realised…

[pruthviraj-gaikwad]

This issue usually happens when the GitHub OAuth handshake fails on macOS, and it’s almost always caused by one of these:

✅ 1. ChatGPT app blocked from opening the GitHub auth URL

macOS sometimes blocks apps from opening external login URLs.

Try:

• Quit the ChatGPT app
• Reopen it
• Try GitHub connect again
• When macOS asks for permission to open your browser, click Allow

✅ 2. Browser blocking the authorization page

If your default browser has strict privacy or extension rules (AdBlock, Ghostery, etc.), the GitHub OAuth page may fail to load.

Try:

• Temporarily disable extensions
• Or switch your default browser to Safari/Chrome and retry

✅ 3. Existing OAuth session is stuck

Even if ChatGPT doesn’t show a connection, GitHub may have a partially created authorization.

Check here:
GitHub → Settings → Applications → Authorized OAuth Apps

If “ChatGPT” is listed, remove it, then retry connecting from the app.

✅ 4. Network or proxy interference

If you're on a work network, VPN, or proxy, GitHub OAuth redirects may be blocked.

Try:

• Turn off VPN/proxy
• Try on a different network (hotspot works as a test)

✅ 5. ChatGPT app cache issue

A reset sometimes fixes it.

macOS:

1. Quit the ChatGPT app
2. Option-click the app icon
3. Select Developer → Reset App State
4. Reopen and try again

If none of these help

It may be a temporary outage on either GitHub OAuth or OpenAI’s OAuth bridge.
You can check:

• GitHub Status: https://www.githubstatus.com
• OpenAI Status: https://status.openai.com

If both are green, the cache reset (above) usually resolves it.

---

Hope this helps — let me know if you need a simpler step-by-step!

[realnotsteve]

Thank you for your assistance.

[ishanrajsingh]

Additional Troubleshooting Steps
Since the standard fixes haven't worked, try these advanced solutions:

1. Check GitHub OAuth App Permissions
   The ChatGPT app may be requesting permissions GitHub temporarily disabled:

Go to https://github.com/settings/developers

Click "OAuth Apps" tab

Look for any pending authorization requests

If you see ChatGPT-related entries, delete them completely

2. Test OAuth Flow Manually
   Open Terminal and test if GitHub OAuth is working:

bash
curl -I https://github.com/login/oauth/authorize
If you get a non-200 response, GitHub OAuth may have temporary issues in your region.​

3. macOS Keychain Conflict
   Sometimes macOS Keychain stores corrupted GitHub tokens:

Open Keychain Access app

Search for "github" and "openai"

Delete any related entries

Restart ChatGPT app and try reconnecting

4. DNS Resolution Issue
   Your Mac might be resolving github.com to a cached/stale IP:

bash

sudo dscacheutil -flushcache
sudo killall -HUP mDNSResponder

5. Check ChatGPT App Version
   OpenAI may have pushed an update that fixes this:

ChatGPT menu → About

Compare your version with latest on https://openai.com/chatgpt/download/

Reinstall if outdated

If Still Failing
Since you found Google results showing others with the exact same error, this is likely a temporary backend issue between OpenAI's OAuth bridge and GitHub's API. The fact that there are minimal search results suggests it's either very new or intermittent.​

Best immediate workaround: Use the ChatGPT web version at https://chat.openai.com/ which has more stable GitHub integration until the macOS app issue is resolved.

Report this to OpenAI support with your macOS version and ChatGPT app version - they may be tracking this specific OAuth regression.

[realnotsteve]

Thank you for your creative troubleshooting. I'm just realising that you were the one who suggesting using the website—thank you, that lead to the solution.

[E5Anant]

This usually happens when GitHub has a stuck or incomplete OAuth authorization for the ChatGPT app, even if nothing appears in your connected apps. Try clearing old tokens at https://github.com/settings/tokens, sign out and restart the ChatGPT app, then try again. If it still fails, GitHub Support needs to reset the stuck OAuth entry on their side.

[realnotsteve]

Thank you for your diagnostics.

[realnotsteve]

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Receiving this message whenever I try to connect chatGTP macOS app to GitHub. Other macOS apps are connected. There is no existing connection from chatGTP. Any ideas? Thanks.

I am posting the solution as reply so I can mark it as the solution. Thank you everyone who made suggestions. I did try all of these things, and there are certainly misconfigurations where those suggestions would work. EDIT: ishanrajsingh made the suggestion to try the web browser, and that lead to the solution.

This particular error message, which I am apparently the very first person to experience, is a result of a bug in chatGPT, and two errors in chatGPT's reasoning.

---

The Bug

The bug is that the application simply does not truly understand how to connect to GitHub. It may be a case of two-factor authentication being required—I'm not sure, as I also used a different point of initial ingress (i.e., web browser) to trigger the required connection security settings.

I say that it doesn't understand, as I get the distinct impression that the app's procedural logic is also dictated by machine learning. That's lazy and poor engineering. In my queries of chatGPT regarding this problem, it provided vague explanations claiming that the connection protocols were always changing, so it couldn't be expected to know them all. But that sounds more like they are relying on machine learning to determine the connection protocols at any given time, rather than use specific procedural algorithms and offer programme updates as standards change.

The work-around:

0. Quit out of the chatGPT desktop app.
1. Log into chatGPT via a browser.
2. Follow the standard menus to add GitHub integration.
3. If not enabled, you will be asked to enable two-factor authentication. Do it via your phone (i.e., a code).
4. Follow the on-screen prompts to connect to GitHub. You'll go through many handshaking screens, some of which are redundant.
5. Eventually, you will get the handshaking screen from when you attempted the connection from the chatGPT app.
6. Continue, clicking the connection button.

The connection will now (hopefully) work.

---

Reasoning Error #1

This is based on queries to chatGPT on how to connect the desktop app to GitHub, and its attempt to diagnose any problems.

chatGPT does not realise that two-factor authentication may be required, and does not think to suggest using the web browser. Instead, it gave me instructions for the app which were impossible to follow—using contextual menus that did not exist, clicking icons that didn't exist.

When I asked why it was so poorly informed about its own app, chatGPT replied that it is impossible for chatGPT to know the apps that implement it, and could therefore not provide solutions. When I pointed out this was the official chatGPT app, it reiterated that knowing that app's capabilities was impossible. And while technically that's not Turing-decidable, it simply points to machine learning in place of proper procedural algorithms.

And as it happens, the solution is impossible to implement using the desktop app, at all.

---

Reasoning Error #2

This is the more serious error. It is based on chatGPT's inability to provide understanding on the GitHub integration feature, conceptually (i.e., independent of any app-specific implementation).

I asked chatGPT how it could have access to all my source files at once. It said to use GitHub integration. And because I couldn't get the connection to work, I was unable to use GitHub integration.

However, if the GitHub project is public, chatGPT does not GitHub integration at all. This entire exercise was unnecessary. It seems that chatGPT's supreme confidence in itself is a shortcoming. I don't see a lot of "maybe", which is a critical component of effective reasoning. (I am new to chatGTP.) Instead of embracing the fuzzy nature weighted learning, chatGTP appears to be using it simply to select between specific solutions it has read on the web, aggregated based on contextual similitude.

---

I hope this helps others who are dealing with these issues.

[jednsoph]

Thank you!!! I encountered the same issue and connecting via the web indeed worked. 🙏

[Diliwije]

This error, "Failed to connect to GitHub. Please try again later," typically indicates an issue with your network, local machine configuration, or a temporary outage on GitHub's side.

Here is a short answer for solving this:

Try these common solutions:

1. Check Network Connectivity: Ensure your internet connection is stable and working properly.
2. Verify GitHub Status: Check the official GitHub Status page to see if there are any current service outages.
3. Check Firewall/Proxy Settings: Confirm that your firewall or proxy settings are not blocking the connection to github.com (ports 22 or 443).
4. Restart Your Router/Computer: A simple restart can sometimes resolve temporary network issues.
5. Use HTTPS Instead of SSH (If Applicable): If you are using SSH, try switching to HTTPS for your Git operations, or vice versa, to see if the connection method is the problem.

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Would you like a more detailed guide on checking your network or Git configuration?

[realnotsteve]

Thank you for taking the time to answer my question. Appreciated.