Media views not being logged for each user

Server Version#: 1.23.5.4862
Player Version#: Roku - Version unknown

I have a few managed users who only watch a few videos/movies a week on my Plex server. I had put a movie on the server for my father, and after a few days noticed that User Dashboard listing did not have the movies listed that he had watched it. I called him the next day and he told me he had watched the movie in its entirety on my Plex. When I look at his play History, it only shows a music video he never actually played. My brother also confirmed that he had watched more movies and tv shows than were listed on his ‘Last 7 Days’ view list.

Any ideas as to what is happening?

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