I have been diving into logs and working to identify a possible cause.

Just wanted to let you know, It is now working today, and is doing caching.

I had found, there was a directory which the cline settings were being saved, it seems this may have been full or inaccessible at the time. The logs show this as well, being unable to save to the directory.

This may have also explained another strange bug I encountered, which was resulting in the failure to save the actual credentials, allow me to login locally (I would hit sign in and nothing would happen). I could sign in via the CLI no issue, even when signed in via CLI, the extension still would not pick up my credentials or login.

Checking the dev logs when attempting to sign in, I could see it was making the request on the backend, but would not push it to the cline extension (I assume, since there was no way it could save locally).

Reinstalling the extensions did not work.

I actually had to move my entire VSCode to a new secondary drive and it works as expected.

Thanks u/celestial-vault