Plex will not display subtitles on transcoded stream

Server Version#: 1.40.0.7998 (Synology NAS)
Player Version#: Latest/Exact version unknown (Nvidia Shield TV - 2017)
*Been happening for at least a year now.

Whenever a remote user (Nvidia Shield) is streaming a Movie/TV Episode from my server (Synology NAS) and the file has to be transcoded for whatever reason, subtitles do not display. Happens no matter if the subtitle is external or part of the video file and I have tried multiple formats but most if not all are already srt. It seems to only be an android tv issue as I have another remote user using a roku player and when I stream remote from a laptop or phone it does not occur.

The only workaround I have found to work is to find out why the server is transcoding the file in the first place and usually convert/reencode the file to ensure Plex can direct play it, as the problem only occurs when the file is transcoded by plex, but this is far from ideal.

I have tried troubleshooting the issue myself including using the android tv built in to the TV itself for plex and completely wiping and resetting up the Nvidia Shield TV, neither seemed to help.

In a perfect world I would prefer all remote streams to be direct but unfortunately transcodes still have to happen some of the time with my setup/network.

Thanks, any help is appreciated.

Does it matter the type of subtitles?

Not that I can tell:

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