Media Prep (File Naming)

Now Plex is pretty fussy about File naming, and ignore it at your peril. The problem is that you can get away with for a while and think… whatever… I will just carry on with my way. That’s fine, just don’t moan when it suddenly stops working, or won’t match your newly added Movie or TV Shows.

As for File types, well Plex suggest mp4 as the most compatible option, but TBH, I prefer mkv, as it allows for a wider range of audio codecs and from experience I seem to see more transcoding with mp4 than with mkv, not really sure why, but it is what it is, and it’s personal taste.
MKVToolNix can quickly convert an mp4 to an mkv

The Support pages for naming can be found here:
Movies
TV Shows
Music
Personal Media

Movies

Personally I put Movies into folders, 1 for each movie title (This includes the Year of the movie), so each folder could contain The Movie file itself (or multiple Movie Files if I have multiple copies e.g. Remux as well as an encoded version). The folder will also contain any external subtitle files and additional stuff. This si where I have to break with the strict conventions, as I like to keep details of the Src, Video and Audio Codecs in the file. This I put after a – ([space][dash][space]). Both Sonarr and Radarr can provide naming like this.
AFAIK This does not impede Plex matching these files, but I could be wrong.

/Movies
   /Avatar (2009)
      Avatar (2009).mkv
   /The Lion King (2019)
      The Lion King (2019) - Bluray-1080p [DTS 5.1][X264].mkv
      The Lion King (2019) - Bluray-1080p [DTS 5.1][X264].mkv
      The Lion King (2019) - Bluray-1080p [DTS 5.1][X264].eng.srt.mkv
      The Lion King (2019) - Remux-1080p [ATMOS + TRUEHD 7.1][AVC].mkv
      poster.jpg

TV Shows

TV Shows should be organised with a Top level folder then Show Name (Year) then Seasons. This is how I do mine e.g.

TV Shows > 24 > Season 01 > Episodes

Naming of the folder structure is possibly more important than the actual files. The files names need at least the series number and episode number. There are a few acceptable structures. Again AFAIK Plex ignores everything after sXXeXX, so you should be safe with this
Again I prefer more info in my names so this is what I use:

Guilt (2019)
 - Season 01
   - Guilt (2019) - s01e01 - Episode 1 Bluray-1080p [EAC3 5.1][X264].mkv

But you could possibly get away with as little as this:

Guilt (2019)
 - Season 01
   - s01e01.mkv