Server not recognizing media, server mislabeling recognized media

You need to re-name and re-organize your media. Read the documents @JaysPlex linked.

/share/Media/TV Series/HEARTLAND/Plex Versions/Original Quality/HEARTLAND/S01E10.mp4

There are three different TV series named Heartland: 1989, 1994, & 2007. Without the year, Plex has no idea which one to match.

Also, the organization is incorrect. Re-organize per Plex requirements.

After renaming/reorganizing, Plex Dance the entire show.

Example

/TV Series <-- folder added to TV show library
.../Heartland (2007) <-- ShowName (IntroYear)
....../Season 01 <-- "Season" in English
........./Heartland (2007) s01e01.mp4 <-- ShowName (IntroYear); sXXeYY format important.

/share/Media/Movies/PRIME/Watch Tora! Tora! Tora! _ Prime Video and 1 more _crosoft​ Edge_3.mp4

Is this the movie Tora! Tora! Tora!?

If so:

/share/Media/Movies/PRIME/ <-- folder added to movie library
.../Tora! Tora! Tora! (1970) <-- MovieName (year)
....../Tora! Tora! Tora! (1970).mp4  <-- MovieName (year).ext; ext=mkv/mp4/etc.