Nvidia Shield (2017) Playback Issue

Server Version#: Version 1.31.1.6716
Player Version#: Version 9.16.1.38616 (f7c22369)

Basically my Nvidia Shield will simply not playback certain files and will just throw up the error

“An error occurred while attempting to play this video. Please check your connection and try again”.

I had a look at the server logs with debugging on while this occurred and the only error that shows up is

“Couldn’t find the file to stream: /transcode/Transcode/Sessions/plex-transcode-3432b97ded4b5af1-com-plexapp-android-980caf7e-0c72-4e9c-8f35-90793af554f1/media-00000.ts”

It doesn’t really tell me anything else and no more context beyond that is given. I don’t experience this problem with any other device. Any help to resolve this is appreciated.

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