Plex no longer updates my libraries

Server Version#:1.23.4.4805-186bae04e
Player Version#: 4.61.2

For some reason, Plex stopped updating my libraries about three months ago. I add files the way I always have in the past and have tried reindexing but nothing seems to work. Is there a solution for this issue?

Can you demonstrate your file names and structure.

Here are a few examples:

RachelleFarelleBirthday.mov

Once.Upon.a.Time.in.Hollywood.mkv

Mr Inbetween - 1x06 - Your Mum’s Got a Strongbox.mkv

Files are named the same as in the past, but still not recognized.

Cheers,

D

You may not have heard this before but naming different to what Plex suggest, may work till it don’t.

Mr Inbetween /
Season 01/
Mr Inbetween - S01E06 - Your Mums Got a Strongbox.mkv

Once Upon a Time in Hollywood (2019)/
Once Upon a Time in Hollywood (2019).mkv

These work perfectly

I also have files similarly named but anything from the last three months will not sync still.