iPhone videos recorded in landscape orientation do not play correctly on playback

Still having a hard time with this. I am running plex on a synology nas. On my tv in my living room, I use Roku ultra with the Plex App. I have a library of home videos originally recorded on various iPhones. The videos that were recorded in landscape will not initially play, it gets to 33% then never loads or plays. If I select direct play forced it will play, but will be sideways, and I have to do that on each video that I want to watch. Is there a way to have it auto rotate and play? If there are settings to change where would I do it? PlexApp, TV, Roku, or PlexMediaSever/Synology NAS?

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