For backgrounds, are you using or have tried the SS chrome extensions and connect the VPN that way?
Alternatively, set the nameservers in settings - network - custom name servers, to SS DNS or 1.1.1.1/1.0.0.1 (Cloudflare), to see if that helps.
Flush DNS cache and reset network settings may also fix some, but as a last resort.
ChromeOS has somewhat a reputation for leaking i.c.w. VPN’s, but hopefully some stuff above works.
I have the same issue except only with Firefox. Passes on Chrome. It does pass if I use the extension on Firefox not when I use the app. It says it fails but still doesnt list my actual ip address which is weird
Thanks for getting back, I need non chrome apps to use the VPN. Support suggested using cloud flare DNS servers, but this didn’t work, also tried Google DNS servers to no avail.
The issue with ChromeOS is that it circumvents VPN’s with IPv6 connections outside the VPN tunnel. In some cases you may have better luck with VPN’s that support IPv6, but no guarantees, unfortunately. If you can access your WiFi router, try to disable the IPv6 protocol.
You can also try a manual setup with an OpenVPN client, as it gives more control.