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Playlist sync to ipad error

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I've made a playlist of my favourite family guy episodes & now I'm trying to sync it to my ipad. When I hit the sync button on the ipad I can see that PMS starts some kind of conversion process (even though the episodes can direct play on my ipad) then after it has converted about 5 episodes it refuses to convert any more. The episodes which have been converted will sync successfully to the ipad but the rest of them have a yellow error message which when pressed tells me "The transcoder encountered an error"

So now I'm left with two problems:

1 - After numerous restarts of the sync process I'm unable to get these particular episodes to convert, even though they shouldn't need converting.

2 - I'm unable to restart the process on the episodes with the errors, any restart or remove I try has to be applied to the whole queue or nothing at all.

This kind of sucks, any advice or help is greatly appreciated.

PMS 0.9.16.5
OSX 10.9.5
Plex for ipad 4.1.1
ios 9.3.1


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