Thanks for sharing those debug logs. Would you be able to test with CLI versions 3.16.0 and 3.19.0? That would help narrow down my search, as those releases include changes that I suspect could be causing this. Once we’ve narrowed down the changes to a specific release it should be much easier to identify the problematic change.
It appears it may be related to the CLI saving to the system keyring. This feature was added in CLI v3.16.0. I’m going to do some more testing and will follow up.