Unable to play files. Plays in VLC fine

I have quite a few files that Plex can not play. VLC plays fine. I enabled debug logs and this is what I get below.

Is this a well known problem with Plex or there is something I can do to work around this?

"type": "log:message",
"level": 2,
"message": "[MDE] Augmented profile: {

“directPlay”: {
“mp4”: {
“mimeType”: “video/mp4; codecs=\“avc1.42E01E\””,
“video”: {
“codecs”: {
“h264”: {}
},
“maxWidth”: 1920,
“maxHeight”: 1280,
“maxFrameRate”: 60
},
“audio”: {
“codecs”: {
“aac”: {},
“ac3”: {}
}
}
},
“mkv”: {
“mimeType”: “video/webm”,
“video”: {
“codecs”: {
“vp8”: {}
},
“maxWidth”: 1920,
“maxHeight”: 1280,
“maxFrameRate”: 60
},
“audio”: {
“codecs”: {
“vorbis”: {}
}
}
},
“ogg”: {
“mimeType”: “video/ogg”,
“video”: {
“maxWidth”: 1920,
“maxHeight”: 1280,
“maxFrameRate”: 60
}
},
“mpegts”: {
“protocol”: “hls”,
“video”: {
“maxWidth”: 1920,
“maxHeight”: 1280,
“maxFrameRate”: 60
}
},
“flv”: {
“video”: {
“maxWidth”: 1920,
“maxHeight”: 1280,
“maxFrameRate”: 60
}
}
},
“directStream”: {
“video”: {
“codecs”: {
“h264”: {}
},
“maxWidth”: 1920,
“maxHeight”: 1280,
“maxBitDepth”: 8
},
“audio”: {
“codecs”: {
“aac”: {}
},
“maxBitrate”: 192,
“maxChannels”: 2
}
}
}",
“time”: “2017-09-04T22:40:30.822Z”
},
{
“type”: “log:message”,
“level”: 2,
“message”: “[MDE] Starting analysis of undefined”,
“time”: “2017-09-04T22:40:30.822Z”
},
{
“type”: “log:message”,
“level”: 4,
“message”: “[MDE] Analyzing direct play”,
“time”: “2017-09-04T22:40:30.822Z”
},
{
“type”: “log:message”,
“level”: 1,
“message”: “[MDE] Direct play failed; unsupported container: undefined”,
“time”: “2017-09-04T22:40:30.823Z”

No, that looks like something is missing from your system.
We can fix it once we know what’s going on.

We’re actually going to need two things after you attempt to play it again.

  1. The log file set you collect (Settings - Server - Help - Download Logs)
  2. The XML ( hover over the item - Get Info - View XML )

Please attach both of those pieces here and we’ll take a look.