No worries, I appreciate the attention you've given me, so thank you.

Yup, I considered that, and it would be near-zero effort given that my files are already alphabetically sorted properly, but I'm pretty sure i have plenty of missing episodes so I would have to manually untick those matches from the episode list

I see. I'll have to mess around with changing the date format in the filename to something appropriate, then change them back to their original name after keeplinking the episodes with filebot.

Thank you for the help

So even without filebot giving me errors, it's not possible to automatically match based on air dates? thetvdb doesn't provide that info via their api?

This is all meant to be picked up by plex btw

1. Here is the path: Z:\downloads\complete\The.Daily.Show.2007.PDTV.XviD-BTN\ under which are all the folders and files I listed in the file tree in my first post. 2. Unfortunately it wouldn't be a good idea for me to rename the files in my download folder, since that would prevent the files from ...

example of what happens: https://streamable.com/altys , https://i.imgur.com/Yob3DXH.jpg The episode numbers are in this format: the.daily.show.02.01.07.dsr.xvid.kyr.proper.avi This is the file tree structure: ├───2007-01 │ the.daily.show.01.08.07.dsr.xvid.crimson.avi │ the.daily.show.01.09.07.dsr.xvi ...