Plex Pre-Roll video doesn't play when starting a movie from a collection

Plex Media Server
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Server Version#: 4.92.0
Player Version#: Roku 7.0.16.7937
I have created a Halloween library that consists of different collections of horror movies. However, the custom pre-roll video I have does not play before any movie that is in a collection inside that library. I have confirmed that it doesn’t work when clicking play on the collection OR when clicking play on a specific movie inside that collection.

However, if I make movies in collections visible inside the library (show items along side their collection), the pre-roll works when playing them from the main library window. This happens on several players including web, so it is not device specific

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