Thanks for the Plex Media Server logs. I can see you are running PMS version 0.9.16.2 Plex for Playstation app version 2.5.7
I can see streaming starting and stopping when transcoding movie to Playstation 3 and Playing direct to Playstation 4. I am not sure if this is what you are referring to. I cannot tell why the Playstation app stopped a few seconds after start. Need to discuss with the team
Playstation 3
Mar 18, 2016 12:16:04 [0x355ed400] DEBUG - [Now] User is 5byfive (ID: 1)
Mar 18, 2016 12:16:04 [0x355ed400] DEBUG - [Now] Device is (PlayStation 3).
Movie /volume1/video/TV Shows/Doctor Who 2005/Doctor_Who_s6e13_the_wedding_of_river_song_720p.AC3.mkv
and was being transcoded
Mar 18, 2016 12:16:04 [0x355ed400] DEBUG - Client [ebdd8752ad81657d411eea61eae88aa9d8c71565] reporting timeline state playing, progress of 1000/2718800ms for guid=com.plexapp.agents.thetvdb://78804/6/13?lang=en, ratingKey=16081 url=, key=/library/metadata/16081, containerKey=/library/metadata/16081, metadataId=16081
Mar 18, 2016 12:16:13 [0x304db400] DEBUG - Client [ebdd8752ad81657d411eea61eae88aa9d8c71565] reporting timeline state stopped, progress of 3000/2718800ms for guid=com.plexapp.agents.thetvdb://78804/6/13?lang=en, ratingKey=16081 url=, key=/library/metadata/16081, containerKey=/library/metadata/16081, metadataId=16081
Mar 18, 2016 12:16:14 [0x355ed400] DEBUG - Client [ebdd8752ad81657d411eea61eae88aa9d8c71565] reporting timeline state playing, progress of 1000/2718800ms for guid=com.plexapp.agents.thetvdb://78804/6/13?lang=en, ratingKey=16081 url=, key=/library/metadata/16081, containerKey=/library/metadata/16081, metadataId=16081
Mar 18, 2016 12:17:54 [0x355ed400] DEBUG - Client [ebdd8752ad81657d411eea61eae88aa9d8c71565] reporting timeline state stopped, progress of 100000/2718800ms for guid=com.plexapp.agents.thetvdb://78804/6/13?lang=en, ratingKey=16081 url=, key=/library/metadata/16081, containerKey=/library/metadata/16081, metadataId=16081
Mar 18, 2016 12:18:00 [0x304db400] DEBUG - Client [ebdd8752ad81657d411eea61eae88aa9d8c71565] reporting timeline state playing, progress of 1000/2718800ms for guid=com.plexapp.agents.thetvdb://78804/6/13?lang=en, ratingKey=16081 url=, key=/library/metadata/16081, containerKey=/library/metadata/16081, metadataId=16081
Mar 18, 2016 12:18:04 [0x304db400] DEBUG - Client [ebdd8752ad81657d411eea61eae88aa9d8c71565] reporting timeline state stopped, progress of 3000/2718800ms for guid=com.plexapp.agents.thetvdb://78804/6/13?lang=en, ratingKey=16081 url=, key=/library/metadata/16081, containerKey=/library/metadata/16081, metadataId=16081
Mar 18, 2016 12:18:05 [0x355ed400] DEBUG - Client [ebdd8752ad81657d411eea61eae88aa9d8c71565] reporting timeline state playing, progress of 90000/2718800ms for guid=com.plexapp.agents.thetvdb://78804/6/13?lang=en, ratingKey=16081 url=, key=/library/metadata/16081, containerKey=/library/metadata/16081, metadataId=16081
Mar 18, 2016 12:19:05 [0x304db400] DEBUG - Client [ebdd8752ad81657d411eea61eae88aa9d8c71565] reporting timeline state stopped, progress of 145000/2718800ms for guid=com.plexapp.agents.thetvdb://78804/6/13?lang=en, ratingKey=16081 url=, key=/library/metadata/16081, containerKey=/library/metadata/16081, metadataId=16081
There was an error round the first stopped
timeline indication
Mar 18, 2016 12:16:13 [0x2ef2f400] ERROR - handle_stream_read error 104 Connection reset by peer
Mar 18, 2016 12:16:13 [0x2ef2f400] DEBUG - Removed transcode output stream 0x350055f8, active count 1 => 0
Mar 18, 2016 12:16:13 [0x304db400] DEBUG - Request: [::ffff:127.0.0.1:44116] GET /:/timeline?containerKey=%2Flibrary%2Fmetadata%2F16081&duration=2718800&guid=com%2Eplexapp%2Eagents%2Ethetvdb%3A%2F%2F78804%2F6%2F13%3Flang%3Den&key=%2Flibrary%2Fmetadata%2F16081&ratingKey=16081&report=1&state=stopped&time=3000&X-Plex-Device=PlayStation%203&X-Plex-Device-Name=PlayStation%203&X-Plex-Product=DLNA&X-Plex-Token=xxxxxxxxxxxxxxxxxxxx (4 live) GZIP
I will see if one can get any diagnostics out of the Playstation app to go with the server logs
and for the Playstation 4
Mar 19, 2016 13:22:14 [0x37a6a400] DEBUG - [Now] User is Home (ID: 6069055)
Mar 19, 2016 13:22:14 [0x37a6a400] DEBUG - [Now] Device is Mystery 4 (Plex for Sony (PlayStation 4 01.17)).
showing starting and then stopping
Mar 19, 2016 13:22:14 [0x37a6a400] DEBUG - Client [oy0ytgy9bms] reporting timeline state playing, progress of 0/201596ms for guid=, ratingKey=122221 url=, key=/library/metadata/122221, containerKey=, metadataId=122221
Mar 19, 2016 13:22:21 [0x32cd7400] DEBUG - Client [oy0ytgy9bms] reporting timeline state stopped, progress of 6000/201596ms for guid=, ratingKey=122221 url=, key=/library/metadata/122221, containerKey=, metadataId=122221
Movie was /volume1/music/Nik West/Just In The Nik Of Time/11 No Choice.m4a
and it was Direct Play
Mar 19, 2016 13:22:13 [0x30861400] DEBUG - Request: [::ffff:192.168.1.110:50372] GET /library/metadata/122221?X-Plex-No-Cache=14584081333103682&X-Plex-Product=Plex%20TV&X-Plex-Version=2.5.7&X-Plex-Client-Identifier=oy0ytgy9bms&X-Plex-Platform=Mystery%204&X-Plex-Platform-Version=531.3&X-Plex-Device=Sony%20%28PlayStation%204%2001.17%29&X-Plex-Device-Name=Plex%20for%20Sony%20%28PlayStation%204%2001.17%29&X-Plex-Token=xxxxxxxxxxxxxxxxxxxx&checkFiles=1&includeChapters=1 (5 live) TLS GZIP
Mar 19, 2016 13:22:13 [0x30861400] DEBUG - Auth: We found auth token (xxxxxxxxxxxxxxxxxxxx), enabling token-based authentication.
Mar 19, 2016 13:22:13 [0x30861400] DEBUG - Updating part with ID=208180 [/volume1/music/Nik West/Just In The Nik Of Time/11 No Choice.m4a]
Mar 19, 2016 13:22:13 [0x30861400] DEBUG - It took 0.0 sec to serialize a list with 1 elements.
Mar 19, 2016 13:22:13 [0x2ebed400] DEBUG - Completed: [::ffff:192.168.1.110:50372] GET /library/metadata/122221 (5 live) TLS GZIP 70ms 1264 bytes 200 (pipelined: 166)
Mar 19, 2016 13:22:14 [0x37a6a400] DEBUG - Request: [::ffff:192.168.1.110:64439] HEAD /library/parts/208180/file.m4a?X-Plex-Token=xxxxxxxxxxxxxxxxxxxx (6 live) TLS
Mar 19, 2016 13:22:14 [0x37a6a400] DEBUG - Auth: We found auth token (xxxxxxxxxxxxxxxxxxxx), enabling token-based authentication.
Mar 19, 2016 13:22:14 [0x37a6a400] DEBUG - Content-Length of /volume1/music/Nik West/Just In The Nik Of Time/11 No Choice.m4a is 7007599.
Mar 19, 2016 13:22:14 [0x37a6a400] DEBUG - Completed: [::ffff:192.168.1.110:64439] HEAD /library/parts/208180/file.m4a (6 live) TLS 58ms 0 bytes 200
This was the last request from the Playstation 4 app
Mar 19, 2016 13:22:15 [0x32cd7400] DEBUG - Request: [::ffff:192.168.1.110:49293] GET /library/parts/208180/file.m4a?X-Plex-Token=xxxxxxxxxxxxxxxxxxxx (7 live) TLS
Mar 19, 2016 13:22:15 [0x32cd7400] DEBUG - Auth: We found auth token (xxxxxxxxxxxxxxxxxxxx), enabling token-based authentication.
Mar 19, 2016 13:22:15 [0x32cd7400] DEBUG - Request range: 5242880 to 7007598
Mar 19, 2016 13:22:15 [0x32cd7400] DEBUG - Content-Length of /volume1/music/Nik West/Just In The Nik Of Time/11 No Choice.m4a is 7007599.
Mar 19, 2016 13:22:15 [0x2ebed400] DEBUG - Completed: [::ffff:192.168.1.110:49293] GET /library/parts/208180/file.m4a (6 live) TLS 198ms 1764719 bytes 200
Are these the failures you are referring to?
Could you get the media info for both of these please
See https://support.plex.tv/hc/en-us/articles/201998867-Investigate-Media-Information-and-Formats