Over the years there have been numerous complaints about Plex not providing a fix to mostly Mobile Phone Videos having incorrect Orientation (Portrait/Landscape) when displayed. I have a time-consuming workaround on a file-by-file basis.
Download a free Encoding App like Handbrake. Do the following:
Re-encode changing the Orientation. In Handbrake go to Dimensions Tab. If video currently displays incorrectly as Horizontal/Top Left, choose 90 [degrees]. Re-encode.
The default new file will be in a OneDrive Video folder. Rename the video file appending something like “_90.” Then cut and paste this file in the Folder of your original. You may choose to keep both versions , or not. Problem solved. Except, you must do this with EVERY offending video, – very time-consuming. The better solution is a Plex software fix.