Hi all -
Suddenly this week, 2 regular users of the ChatGPT macOS desktop app started getting a certificate error when opening macOS ChatGPT (desktop app).
I resolved this by exempting ChatGPT from our VPN SSL Inspection, but normally there is a way to configure a desktop app struggling in this manner to use the appropriate certificate. I can’t find any documentation anywhere on this so curious if anyone else has any pointers.
Don’t have an answer for you, but we’ve been seeing the same issue.
Same here but using Cato VPN and see the same on iOS and macOS. Was working perfectly happy until a few days ago, so something has changed??
Same. Unfortunately, the way to bypass is not recommended in my company due to security reason.
I am seeing this for ZScaler, its very frustrating
I had this very same problem with my work mac. My company also uses ZScaler.
It was working and then it stopped out of nowhere…
For a moment I thought the IT department had blocked it, but it turns out all I had to do was completely uninstall it.
And by completely I mean… not by just deleting the App, but using AppCleaner or similar.
Then I’ve reinstalled it and it started to work again.
I am 99% sure that it will happen again, but at least I know how to make it work now 
Hope that helps some of you.
This all started when our end user updated to the latest MacOS desktop app of ChatGPT Version 1.2024.240 (1725405916). Older version of the desktop app is not seeing this issue (certificate pinning).
Same issue here. There should be a setting or something to accept the certificate in these cases.
This update broke it for us too. It would be great if there was a way to configure the cert in the app.
Is there a place that lists all the older versions so I can roll back?
Looks like OpenAI just release an update and now it’s working again with Zscaler SSL inspection (certificate pinning).
Newest update (1.2024.247) does not fix SSL inspection for our Palo firewalls.
Has anyone found a way to import other Root CAs into the store for ChatGPT to trust?
How did the issue get solved for Zscaler?
I’ve updated to 1.2024.247 and it works with ZScaler.
I exempted OpenAI traffic from SSL Inspection in Zscaler. OpenAI isn’t publishing anything helpful re: supporting their desktop app and I don’t want to keep dealing with their issues as they make breaking changes silently.
Still facing this on 1.2024.254 when using with Netskope (goskope) security.
Looks like SSL inspection exclusion is the only way to get this working.
In the case of ZScaler, inspection is possible because the hash value of the ZScaler Root CA is hard-coded into the ChaptGPT App to form a root CA trust chain. We have requested the same for Nestkope, so we expect inspection to be possible soon.
Zscaler is whitelisted. To read about the ChatGPT macOS certificate pinning mechanism google “OpenAI Limits Data Inspection for (Most) Organizations”
It would be nice to have this configurability. Either to import certs to trust, or else disable verification.
