How can I tell why my video doesn't play?

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Player Version#: Chrome for MacOS 86.0.4240.75

So I’m trying to play a ripped Blu-Ray of Captain America: Civil War from a Mac Mini to my Macbook Pro using Plex. I’m in the back bedroom so it may be that I don’t have the bandwidth to play the MKV file, but it isn’t failing and it isn’t running and stuttering or anything, it’s just spinning, on and on, 10 minutes now without playing and without an error. How can I tell why it isn’t playing?

The file itself plays fine on it’s own over my wifi network to this room using regular file sharing and VLC. I’d like to know whether it’s trying to transcode the file, or trying to play it directly, so I can try to troubleshoot it. Can someone give me some pointers?

Enable logging in the Web app, playback the file again, after 1 minute of it not working, stop playback and grab the logs and post them here. https://support.plex.tv/articles/201611836-plex-web-app-logs/

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