Doing that fixed it, however if there’s a long term solution (clearly this is a bug) rather than fixing it on a per item basis, I’m all ears.
Also, it seems like Refresh Metadata should do this, but clearly isn’t.
As I thought. You need to start with a 0 not a 1. See my earlier comment for how to fix. Then just rescan library and it will see it fine.
Huh…First line starts with a 1
Well Plex Dance fixed it so its doable I think.
Yeah there are a few ways to fix it. Easiest I’ve found is just editing the file in place rather than moving things around for the plex dance. Is also far easier and quicker to automate checking every srt file and fixing it with a shell script this way.
Yeah according to the “spec” they start with a 1 but it seems Plex prefers 0 
at least most of the time.
Never EVER seen that!
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I am 99% positive I don’t have a single subtitle file beginning with 0.
Almost all of my videos have a subtitle (embedded or as an external .srt file) They are all encoded with UTF8 , they all have the proper extension of “srt” (not txt) - and they all work and display in every device properly.
I would make a wild guess, that by simply editing the file and re-saving it, some formatting issue was repaired. I would even make another guess - if you re-edit the file and remove the “0” lines you added, that the file will work and be recognized by Plex.
My two cents, for what it’s worth. 
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I have tried many things. Removing the start on 0 and Plex then fails to see the file like before. Changing encoding (Windows to UTF-8, etc) didn’t help.
If the srt file is embedded in the mkv it seems Plex works with it starting with a 1. If it is an external file alongside the mkv file it seems Plex gets grumpy about it not starting with a 0. Sometimes doing the Plex Dance fixes things, sometimes not.
I don’t know why obviously but as the edit fix is simple I just check and fix before I put it on my Plex server.
What ever caused this, is now most likely no longer in the logs, since they roll over 
Next time it happens, provide us with a zip of ALL the logs, asap
You have something else going on, and again, without logs right after it happens, we are clueless.
Your cure is however 100 % wrong, since you are invalidating the srt files, and simply are so lucky, that the Plex Players are forgiven about this, at least for now.
As @leelynds said, when altering a file, and saving it, can cause formatting changes inside the file, but I personally think, that it get’s detected simply due to a new timestamp.
As such, a simple change could also be to change the name of the srt file from like mymovie.en.srt into mymovie.eng.srt or visa versa
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Understandable. I’m attaching mine just in case.
If that were the case why does editing the file again back to 1 cause Plex to fail to load the subtitle?
I have tried other edits to the file, renaming it, changing encoding, etc. which did nothing. Adding a 0 first fixes it 100% of the time in my experience.
The other option is to use mkvtoolnix to merge the srt file into the mkv. I have done this with srt files Plex refuses to see and they work just fine.
Perhaps I am just lucky but if it fixes things every time I’m not gonna complain
No idea, without logs!
Only entry in LMA logs was sadly this:
2020-03-10 13:06:48,179 (-4fa01ba0) : INFO (subtitlehelpers:143) - Found subtitle file: /mnt/media/Movies/The Kitchen (2019)/The.Kitchen.2019.1080p.BluRay.x264-DRONES[rarbg].en.srt language: en codec: srt format: srt default: forced:
So yes, it rolled over 
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