Thanks for the response Elan.
I can confirm that I can clear the issue with the steps listed above.
I can reproduce the issue by pausing the playing track. then going about my business for a while (usually hours). And then when I reopen the app and try to resume where I left off, then it happens (sorry not very precise)
on the 404s - I realised today that I have removed a bunch of music files without clearing the trash, that could explain that? In terms of playback, plexamp will skip over the missing track successfully.
I have attached fresh plexamp logs, and server logs too.
Plexamp-Logs-2026-01-28-1.zip (113.7 KB)
Plex Media Server Logs_2026-01-28_19-06-47.zip (1.6 MB)
Thanks.