Unauthorized also. You could zip up your debug log folder and attach it for us.
Context helps us figure it out. You did a great job investigating the cached image.
https://support.plex.tv/articles/202967376-clearing-plugin-channel-agent-http-caches/
I guess that means you followed the above article? Okay then, with any issue network issue, I’d restart all my hardware first, then capture the logs after PMS has been running for 10min.
You can also just try to Plex Dance the show away and put it back after reboot. That would force it to fetch anew, making for interesting logs.