Umm… I’m not familiar with IIS and have never used it, I’ll set my system up to use IIS over the weekend and see if I can replicate/fix the issue. Sorry I can’t be more help 
Thanks for your help so far. I know it is an unsupported feature so I´m patient :)
If only I could get subtitles on the movies without transcoding then I wouldn´t need to touch the settings.
Trying to create a MP4 file with the subtitle file embedded. It just take A loooong time since it needs to reencode the Audio to AAC (Trying MKV2MP4)
Sorry to revive and old topic, but I'm having the same issue, and was wondering if this was ever solved.
I'm running plexconnect on Windows Server 2012 R2 following this guide.
https://forums.plex.tv/topic/147160-another-server-2012-r2-iislocal-dns-guide/
I'm unable to change any settings in the plexconnect app on ATV3
Very frustrating, please help!
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