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For all TV series the have an episode number over 100, nothing shows up past 100. I have the Daily show, and Stephen Colbert, and the last episode I can see in each season of these series on the web client and the Mac client and iOS client is episode 100. I have episodes 101-105 of Stephen Colbert for the latest season, but the clients show 100 as the last episode.
Can you give an example file name/path for one of the episodes which isn’t showing up correctly? If they’re named according to Plex’s guidelines they should be properly identified.
The Late Show with Stephen Colbert - S01E101.ext
(Don’t mind the preview poster, I tested with a renamed episode of Eureka, but note the episode number)
There are some other issues going on right now which cause metadata not to pull, but that’s a separate problem.
I use a Mac as my share, and have the files in iTunes/TV+ app, so for example these are the last 6 file names:
Is there an option to have it in both iTunes and Plex and have it work? Can it work with the names iTunes tags it with?
You need to name them correctly, copy from the iTunes directory.( Found in your Music Folder) Correct the naming to the same as Philipsw said above. Point a Plex Library to you new Directory collection that has had it’s naming corrected.
So you are saying I have no option to use the apple standard naming?
Not if you want it to work in Plex,
Example: S??E104 Sanjay Gupta Maria Bamford (1080P).m4v
Okay I am renaming them that way after they get copied into the TV app so as those will work with Plex. I am just doing that for episodes 100+. Maybe this can change for the future because everything else works with the Apple naming.
You will need to separate them to a folder outside of iTunes and link to PMS
I did this:
Within the iTunes folder, and both iTunes and now Plex are handling it fine. I just have to manually change the names for the files over episode 100…
If it works that’s amazing. Good find. Would not have expected that to happen without consequences. 
It just means I have to do another step when I add episodes over 100. I will see if I can do something with my iFlicks app or with iTunes (in my case the TV app) to automate it.
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