You have naming issues.
My canned response is to see https://support.plex.tv/articles/naming-and-organizing-your-tv-show-files/ and:
If you want to save yourself a lot of time I would recommend using Download - tinyMediaManager and use ${title} (${year}) {imdb-${imdb}} as the new name format.
Folder format:
${title} (${year})
(Please note I linked to the v3 which is free to use)
Worst case you can do an export with Releases · WebTools-NG/WebTools-NG · GitHub which should help you locate the miss-matched file. (You could also plex dance it, and then look at date added)
