I have experience some of the issues here, specially the one when subtitles don’t work but they do when in PiP mode.
I went to settings and turn off “override subtitle style” and Plex started showing them again in the main video. This might be helpful.
It used to work for both direct server playback and synced content. If you set it to automatic on the app settings - advanced - Burn subtitle setting set to Automatic.
You can go to the synced content and keep clicking on the picture in picture mode icon in the player (1st click it pauses, but you do it again) and it’ll show the subtitle.
keep note: Make sure that you have the Picture in Picture mode setting turned off else it’ll move to the smaller view.
I hope one of the devs sees this and responds.
It’s really annoying
Don’t hold your breathe on that happening, it has been over 4 months now since this was first reported and we have not heard a single thing from any of them on here, not even an acknowledgement that they are aware of the issue 
Same problem here. My mother downloaded an Italian spoken film from my server to watch on her iPad which has English and Dutch subtitles included, but they didn’t show up.
Naturally I thought it was her own doing that things didn’t work out but I didn’t get it to work either. So I’ve tried a couple of other videos and used different settings but nothing seems to work for me.
I’ve also checked the optimized file on my PC (something thats not really possible on an iOS device afaik) and you can see the “Plex Version” folder with the original movie title and the SRT files with the same movie title and language additions. I do not understand why the subtitles won’t show up on an iOS device.
I really hope a fix is out soon with the pandemic being tampered and the holiday season coming up.
Guess they working on a new type of synced content called Downloads.
Check this thread posted by an Plex employee. Hopefully they will role this out to iOS soon.
Was experiencing the same issue and using the older video player setting has worked for me. Hope the devs fix this, but better than nothing.
Hello everyone. Please see Sync is Dead (almost). Long Live Downloads! (Part 2).
All working great again now, and much easier and effective than ever - thank you for the excellent work, Plex team !
(P.S - however, the communication on here could have been a tad better thou)
Finally thank you for the amazing work!
Hopefully communication via the forums would be much faster in the future 
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