Media not reliably marked as watched

Plex Media Server Desktops & Laptops
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Server Version#: Version 1.22.0.4163
Player Version#: Version 4.53.0
Plex Media Server Logs_2021-03-23_10-56-19.zip (961.6 KB)

Hi Team, hoping to get some technical insight here.
Firstly, my setup:

Custom home built server, 2x Xeon 5000 series CPU’s, 64GB Ram, Windows Server 2016.
Plex runs in a ubuntu VM.

Issue I have is that media watched is not being reliably marked as media watched. I understand the process is automatic, however I can watch something from end-to-end and it is not marked as watched.

Where to begin troubleshooting this?

Also, very disappointed that the only presented support option is Community based support, especially seeing as I purchased a lifetime pass… highly disappointing.

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