Shield no longer direct play?

So I am having an issue with a couple of my media files no longer direct playing to my Nvidia Shield.

The files are .MKV container, housed on my Synology DS716+II NAS, and all media devices (Nvidia Shield/LG OLED/Apple TV 4K/etc.) are using Ethernet. The files in question have been on the server for a while and I have never had any issue playing them on my Shield or even LG OLED Plex App as they always direct played flawlessly. Then, I updated the Shield to 8.0 and updated the Synology NAS to the current/latest OS and noticed the media files would not play correctly (i.e. being transcoded to h264 from VC-1). I have updated Plex to the x64 variant on the NAS as there are known issues with the current NAS build. Still no luck in getting those media files to direct play. Any help would be greatly appreciated to get my files to work like they used to as the NAS is not powerful enough to transcode on the fly.

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