Plex Skipping a file in a folder and then re-scanning folder each time

Server Version#: 1.19.4.2935 W10x64

I have a folder contained 389 episodes of a tv show. Plex seems to always skip over episode 364 when scanning for some odd reason. I have this issue with some other files too. Naming is the same on all files and it plays fine. Log entry below shows it skipping over the file and never referencing it at all:

Jun 29, 2020 17:28:05.136 [4300] DEBUG - Looking for path match for [C:\TV\Cartoon Shows\Tom and Jerry Cartoons Complete Collection (1940-2007) [DVDRip]\263 Tom The Babysitter [1991].avi]
Jun 29, 2020 17:28:05.136 [4300] DEBUG - Path matched, we're reusing media item 1287404
Jun 29, 2020 17:28:05.169 [4300] DEBUG - Looking for path match for [C:\TV\Cartoon Shows\Tom and Jerry Cartoons Complete Collection (1940-2007) [DVDRip]\265 Mess Hall Mouser [1991].avi]

Additionally, when re-scanning the folder. Plex sees that it only has 388 files scanned in, but 389 files are present so it always tries to re-scan the entire folder. This is slow since all files are on a remote so it downloads a piece of all 388 files at every scan. Any thoughts on what can cause this?

Jun 29, 2020 15:04:02.272 [16344] DEBUG - Scanner: Processing directory C:\TV\Cartoon Shows\Tom and Jerry Cartoons Complete Collection (1940-2007) [DVDRip] (parent: yes)
Jun 29, 2020 15:04:02.623 [16344] DEBUG - Directory had 389 files, database had 388 files, can't skip.
Jun 29, 2020 15:04:03.327 [16344] DEBUG - Looking for path match for [C:\TV\Cartoon Shows\Tom and Jerry Cartoons Complete Collection (1940-2007) [DVDRip]\003 The Night Before Christmas [1941].avi]
Jun 29, 2020 15:04:03.327 [16344] DEBUG - Path matched, we're reusing media item 1287144

That’s not how TV shows work in Plex.
You won’t be able to solve this without reorganizing and remaining.

I understand they are not optimally named but it is a remote folder where I only have read only access. All files in that folder use the same naming scheme and it picks up 388 of 389 of them. It doesn’t seem to even attempt to access the last file even though it knows it is present.

If you cannot change these files, you may have to use an ‘Other Videos’ library and the ‘folder’ view mode.

I appreciate your reply, thank you. I’m not sure this gets to the heart of my question, perhaps it’s a poor example of the phenomenon I’m seeing in several folders but it’s the one I had the log information to show. Basically the issue is Plex scans a folder, sees 389 files, sees it only has 388 previously scanned files in its database so traverses all files in the folder looking to add one more. (whether they are matched with metadata or not is irrelevant at this point)

The issue lies with it not even attempting to read the one file that it is missing. It reads 388 files going from episode 263 to 265, always skipping 264. Every time it scans, it runs into this same issue with this file. Again just one example but is happening to a few dozen files, all of which are functional and named exactly like the rest of the folder

If your file naming is not compliant, it is not worth trying to solve such an issue. Because it could very well be caused by the non-compliant file naming.

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