This is a 5 year old bug and still not working as of today…
This will only play part one in the webplayer… but will play both parts on the android TV app.
Cheers F
The:
-partX
goes at the end
and there’s no space between the - and the partX
21 Jump Street (1987) - S04E10 - Wheels and Deals (2) [480p]-part1.mkv
21 Jump Street (1987) - S04E10 - Wheels and Deals (2) [480p]-part2.mkv
Output of ls, as you can see there is space, just not very visible in Web GUI.
'21 Jump Street (1987) - S04E10 - part1 - Wheels and Deals (2) - [480p].mkv'
'21 Jump Street (1987) - S04E10 - part2 - Wheels and Deals (2) - [480p].mkv'
The examples and naming in the page you pointing to has the partX just after episode numbering… well it doesn’t say it clearly where it should be… but think it’s pretty clear form reading that is should be before optional data such as resolution and episode name. There is clearly spaces at least… but can try what u suggest.
Cheers F
You have a lot of - in your file name.
typically you’re allowed 2, not 3 - but I would stick the -partX at the end - as a test if nothing else so it’s the last thing Plex sees.
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The reality is that episode name is not required to match from what I have experienced
No think it’s mainly to make it look neat and tidy so to say.
So when you use your server and clients the name of Episode is populated with Plex Agents. So I don’t get neat stuff in this case. It really sounds like OCD. Lol 
The Episode Name is handy - when you have to fix an off-the-wall match and the name is right there on the page you’re editing.
Correct Juice but is that the case here. A well known TV show.
I’ve been fixing wild TMDB TV Show data often.
I expect it will be a regular thing in the coming years.
Well in that situation, it’s time to dig deep. Agreed… Find the ID and drill
Well OCD or not, Plex as good as it is might change and you move to some other solution and if you done naming thoroughly which aint hard with filebot then it might be easier for you to switch.
I guess the point is - complex file names with multiple hyphens, parenthesis, brackets and a brand new agent that’s still being potty-trained - if something doesn’t work as expected - do something else…
I might even drag everything off that file leaving only the show name, the S04E10 and the -partx
if it doesn’t work then - get the tongs - we have a roach.
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I do agree with that scenario you propose, just trying to move past three - in a naming to have this fixed.
Plex matching works till it belly flops, so the match plan can be very tailored at times. 
This is the only way this is working in Plex.
Official documentation for TV shows: https://support.plex.tv/articles/naming-and-organizing-your-tv-show-files#toc-5
for Movies: https://support.plex.tv/articles/naming-and-organizing-your-movie-media-files#toc-2
The only alternative approach is to merge the two files: [HowTo]: joining multi-part movies files with MKVtoolnix GUI
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