Thanks for the screenshot.
The problem is the file names and organization.
You need to rename and reorganize your files according to Plex naming requirements.
See Plex Documentation → Your Media
After you have renamed and reorganized the files, perform the Plex Dance.
For example:
/volume2/Videos/HD-Movies <-- Folder added to Plex library
.../300 Rise of an Empire (2014) <-- Movie_Name (year)
....../300 Rise of an Empire (2014).mkv <-- Movie_Name (year).ext ext=mkv/mp4/etc.
If you wish to keep the information such as resolution in the file name, place it inside square brackets at the end of the file name.
/volume2/Videos/HD-Movies <-- Folder added to Plex library
.../300 Rise of an Empire (2014)
....../300 Rise of an Empire (2014) [1080p etc etc].mkv
