Movies deleted on the Plex app not being deleted off my Synology NAS

Plex Media Server NAS & Devices
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Server Version#:4.145.1
Player Version#:
<If providing server logs please do NOT turn on verbose logging, only debug logging should be enabled>

For perhaps years ive been deleting movies after watching them on the plex app while keeping others. I recently noticed I was running low on disc space and discovered none of the files I deleted from plex (although they were removed from the plex library) we’re actually being deleted off the server.

Whats the easiest way to re-sync this without painstakingly trying to match the library with the NAS directory folder by hand? Can I resync the folder without losing all my watch history (Not an issue with movies but wouldnt want to lose it on TV shows)

As a secondary consideration, WHY wernt they being deleted off the server? Ive a Synology NAS buut using the native app (not Docker)
Empty recycle bin on re scan is ticked

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OK nevermind, it seems it is deleting the VIDEO file, just not the parent folder. So ive dozens of empty folders to clean up but no wasted space.

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Which is kind of expected, Plex deals with specific files, and plays it safe to avoid deleting things it shouldnt.

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