Thanks for that 
From your server logs:
Dec 01, 2024 17:03:10.648 [139625836718904] DEBUG - [Req#33cc] Whacked session fedhyixcf2sgqxpa9et2leyb, 0 remaining.
Dec 01, 2024 17:03:10.652 [139625903864632] ERROR - [TranscodeOutputStream] Streaming Session 0x7efd30db06a8 appears to have died from under us
Dec 01, 2024 17:03:10.652 [139625903864632] DEBUG - Removed transcode data consumer, active count 1 => 0
Dec 01, 2024 17:03:10.652 [139625841052472] DEBUG - [TranscodeOutputStream] Input processing thread exited after writing 202582 bytes, m_closed=1, m_endOfFileReached=1, session->isStopped()=1
Dec 01, 2024 17:03:10.652 [139625914272568] DEBUG - Jobs: '/volume1/@appstore/PlexMediaServer/Plex Transcoder' exit code for process 25910 is -9 (signal: Killed)
From your app logs:
Dec 01, 2024 17:09:00.479 [0x70000ba06000] ERROR - [MPVEngine] something happened.
Dec 01, 2024 17:09:00.479 [0x70000ba06000] DEBUG - [MPVEngine/mpv] cplayer: finished playback, something happened (reason 4)
Dec 01, 2024 17:09:00.479 [0x70000ba06000] INFO - [MPVEngine/mpv] cplayer:
Dec 01, 2024 17:09:00.862 [0x7ff84aa6ddc0] ERROR - [Web] [QTMedia(1)] A critical error occurred: 4294967276 An unknown error occurred (4294967276)
Dec 01, 2024 17:09:00.865 [0x7ff84aa6ddc0] ERROR - [Web] [Player] Direct Play failed, but server can transcode. Attempting to fallback to either Direct Stream or transcode...
Dec 01, 2024 17:09:00.887 [0x70000ba06000] DEBUG - Executed command '["stop",]'
Dec 01, 2024 17:09:00.891 [0x7ff84aa6ddc0] ERROR - [Web] [QTMedia(1)] componentWillUnmount rejected: {
"type": "[object Error]",
"stack": "Error: Resolved after unmount\n at file:///Applications/Plex.app/Contents/Resources/web-client/js/main-8792-0816f866d418f1d5f8eb-plex-4.142.1-8a541f3.js:2:3028882\n at async file:///Applications/Plex.app/Contents/Resources/web-client/js/9879-9879-56152506a5288b6b1bee-plex-4.142.1-8a541f3.js:2:751336",
"name": "Error",
"message": "Resolved after unmount"
The server is doing what it is supposed to and transcoding the file in question, then it complains that the rug was pulled out from under it and the session was whacked.
That seems to indicate that the issue is with the Plex for Mac OS app.
The Plex for Mac OS logs complain of an unknown error and then it simply stops. Unfortunately, I am not knowledgeable enough to decipher the Plex for Mac OS logs correctly.
I will ask @ChuckPa if he can pass this on to the appropriate folks at Plex.
With a little luck, they may be able to help you further.