Some media won't play until server host has viewed the video through Plex

Server Version#:1.16.0.1226
Player Version#: Through browser on several different devices Chrome, Firefox and Edge
Plex Media Server Logs_2019-06-30_14-53-56.zip (1.9 MB)

Media files will not open on any devices besides the server itself until they have been viewed through Plex on the server. This issue has been happening for the past few updates. Any help is much appreciated.

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