Ripping, sorting, file is lost?

Plex is probably combining them together (Get Info will show you all the files associated with a given item). If you want them to be separate entries, you should be able to manually split them apart. Another workaround would be to use something like MKVToolNix GUI to merge the two volumes together, since it looks like TMDB/IMDb list it as a single three-hour documentary, not separated into volumes 1 and 2.