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Trouble playing a three files that originally played fine

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Ok I have the latest Plex media server on a mac. They used to play fine before I did the last 2 server updates.

Nothing other than that has changed.
I have an i7 macbook pro with 8gb of ram.

I try playing them on ios, web browser, and xbox 360 all dont work. If I play the file within my mac it works great.

What is confusing is they played well before. So Far I only count 3 movies of mine that wont play. but i have 228 so it will take sometime.

below is the media info of one movie that wont play

Media Info
Files

/Volumes/Video/Films/Star Wars Episode IV A New Hope/Star Wars Episode IV.mkv
Media

Video Resolution 720p
Duration 2:01:50
Bitrate 19323 kbps
Width 1280
Height 720
Aspect Ratio 1.78
Container MKV
Video Frame Rate 24p
Audio Profile ma
Video Profile high
Title Original
Part

Duration 2:01:50
File Star Wars Episode IV.mkv
Size 16.44 GB
Audio Profile ma
Container MKV
Video Profile high
Codec H264
Bitrate 17403 kbps
Bit Depth 8
CABAC 1
Chroma Subsampling 4:2:0
Color Range tv
Color Space bt709
Duration 2:01:50
Frame Rate 23.976 fps
Frame Rate Mode cfr
Has Scaling Matrix 0
Height 720
Level 4.1
Pixel Format yuv420p
Profile high
Ref Frames 5
Scan Type progressive
Width 1280
Codec DCA
Channels 5.1
Language English
Audio Channel Layout 5.1(side)
Bit Depth 16
Bitrate Mode VBR
Duration 2:01:50
Profile ma
Sampling Rate 48000 Hz
Title 5.1 DTS-HD-MA (1977 70mm six track mix)
Codec DCA
Channels Stereo
Language English
Audio Channel Layout stereo
Bit Depth 16
Bitrate Mode VBR
Duration 2:01:50
Profile ma
Sampling Rate 48000 Hz
Title 2.0 DTS-HD-MA (1977 35mm stereo mix)
Codec DCA
Channels Mono
Language English
Audio Channel Layout mono
Bit Depth 16
Bitrate Mode VBR
Duration 2:01:50
Profile ma
Sampling Rate 48000 Hz
Title 1.0 DTS-HD-MA (1977 35mm mono mix)
Codec AC3
Channels Stereo
Bitrate 320 kbps
Language English
Audio Channel Layout stereo
Bit Depth 16
Bitrate Mode CBR
Dialog Norm -31 dB
Duration 2:01:50
Sampling Rate 48000 Hz
Title 2.0 Dolby Digital (1985 Laserdisc mix)
Codec AC3
Channels Stereo
Bitrate 320 kbps
Language English
Audio Channel Layout stereo
Bit Depth 16
Bitrate Mode CBR
Dialog Norm -31 dB
Duration 2:01:50
Sampling Rate 48000 Hz
Title 2.0 Dolby Digital (1993 Laserdisc mix)
Codec AC3
Channels Stereo
Bitrate 192 kbps
Language English
Audio Channel Layout stereo
Bit Depth 16
Bitrate Mode CBR
Dialog Norm -31 dB
Duration 2:01:50
Sampling Rate 48000 Hz
Title 2.0 Dolby Digital (1993 LD Audio Commentary)
Codec AC3
Channels Stereo
Bitrate 192 kbps
Language English
Audio Channel Layout stereo
Bit Depth 16
Bitrate Mode CBR
Dialog Norm -31 dB
Duration 2:01:50
Sampling Rate 48000 Hz
Title 2.0 Dolby Digital (2004 DVD Audio Commentary)
Codec AC3
Channels Stereo
Bitrate 192 kbps
Language English
Audio Channel Layout stereo
Bit Depth 16
Bitrate Mode CBR
Dialog Norm -31 dB
Duration 2:01:50
Sampling Rate 48000 Hz
Title 2.0 Dolby Digital (2004 starwars.com Audio Commentary)
Codec AC3
Channels Stereo
Bitrate 192 kbps
Language English
Audio Channel Layout stereo
Bit Depth 16
Bitrate Mode CBR
Dialog Norm -31 dB
Duration 2:01:50
Sampling Rate 48000 Hz
Title 2.0 Dolby Digital (2011 BD Archival Interviews Audio Commentary)
Codec AC3
Channels Stereo
Bitrate 320 kbps
Audio Channel Layout stereo
Bit Depth 16
Bitrate Mode CBR
Dialog Norm -31 dB
Duration 2:01:50
Sampling Rate 48000 Hz
Title 2.0 Dolby Digital (Isolated Score)
Codec AC3
Channels Stereo
Bitrate 192 kbps
Language English
Audio Channel Layout stereo
Bit Depth 16
Bitrate Mode CBR
Dialog Norm -31 dB
Duration 2:01:50
Sampling Rate 48000 Hz
Title 2.0 Dolby Digital (Commentary For Visually Impaired)
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