Hello MovieFan.Plex, and Hi to Everyone!
I am from the “future” 
and this issue not yet solved.
But, for your consideration, Always I open the movie with “Windows Media Classic” logged on opensubtites.com and save the subtitle in folder the Xbox 360 find the legend by language (English, Spanish, Portuguese, etc). Otherwise, when I put a subtitle fron other source, Xbox 360 does not recognize (and the Server on PC [Windows 10] shown “unknow subtitle”.
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