Plex Media Server Sync problems

I have added a friend of mine to get access to my libraries. He can see and watch the content on his iPhone and iPad but when it comes to sync content down to his units it get stuck. The sync starts but suddenly stops at 50% and become queued for some reason. Any thoughts of what the problem can be?It doesn’t matter if he uses the server that have a mac or the server that uses a QNAP.

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