Adding a file of the same movie but different versions? EX: Movie and movie, the directors cut

Plex will most likely merge both files as different (quality) version of the same movie. Plex currently doesn’t have a concept of different cuts/editions. There’s a widely popular and long-standing feature suggestion which is also discussing how to handle those today – the most common approach appears to be using the Split Apart action from the movie’s context menu and then to manually expand each version’s name / poster.