Just to clarify: you do have these files stored within the necessary folder structure, right?
Because there is no TV show titled “Seth Meyers”. Plex needs a proper show title in order to make a sensible match.
So the folder structure name should at least look like this:
/TV Shows <-- this folder added to the Plex library
/Late Night with Seth Meyers (2014)
/Season 11
Seth.Meyers.2024.01.10.Kurt.Russell.1080p.WEB.h264.mkv
Seth.Meyers.2024.01.09.Dua.Lipa.1080p.WEB.h264.mkv
...
Is this the case on your server?