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Playback Randomly Stops after 5-20 minutes

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So I recently started using Plex to stream playback to both my PC, Android tablet and phone. I have this reoccurring issue on all of my devices, while watching a video it closes randomly returning me to the movie or series info window. No error messages.

Info
Synology DS1815+ DSM 5.2-5644 Update 5 (latest as of today)
Plex Server Version 0.9.16.2 (Intel CPU version) (latest as of today, also happened on previous versions)
My router is an Asus RT-AC66U with the latest Shibby's Tomato firmware installed.

I haven't touched any of the playback settings yet, I was wondering if any of you guys have any recommendations?


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