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Plex issues but not on Jellyfin
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There's probably a codec issue where Plex thinks something can direct play but it can't. I've had similar issues a few times over the years especially with audio codecs like EAC3 for example. Easiest thing to do is to just find a different version of the file and try to avoid that codec for the time being.
Thanks. I will monitor if it happens with certain codecs and then blacklist them.
You can also use Handbrake to encode your files