Waiting to Download/Sync

Plex Media Server
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Server Version#: 1.21.4.4079
Player Version#: latest iPad app version

Whenever I am syncing on the iPad app from my NVidia Shield Server it just hangs on “Waiting…” until I hit sync again and then it goes, then eventually hangs again, over and over and over. Why can’t this just run without my constant attention?

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Same issue here, sync needs an overhaul

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