Trailer MP4 files won't load into the "Cinema Trailers to Play Before Movies" autoplay feature

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The local trailer MP4 files are not loading into the “Cinema Trailers to Play Before Movies” auto-play feature
I have organized the “xxx-trailer.mp4” movie trailers for all local movies and TV shows, and these local “xxx-trailer.mp4” media files are displaying correctly on the movie poster page. However, when I selected the option to play 2 trailer files before the movie starts, it doesn’t load and play my local “trailer.mp4.” I’m not sure what might be causing the issue.

Because I have a lot of movies in my library, I often don’t know what to watch. I want the “Cinema Trailers to Play Before Movies” feature to randomly recommend movies from my library using trailers to make it easier for me to decide. However, my organized local trailer library isn’t randomly playing my local Cinema Trailers properly.

I am a Plex Pass user, and if I select “Include Cinema Trailers from new and upcoming movies in theaters,” it doesn’t play my local trailer files but instead loads and plays online trailer files. I can’t figure out what settings I need to adjust to load my local trailer files.

Make sure to check Settings > [Server Name] > Extras > Include Cinema Trailers from movies in my library to see trailers of movies in your library.
The option Include Cinema Trailers from new and upcoming movies in theaters isn’t looking for new stuff in your library but new trailers in general — using the online sources.

Even with the reference to use trailers of items in your library, Plex might choose an online trailer of one of those items.

I realized the issue was with the age restrictions on the movies. I changed all the movies to have a lower age restriction, and now the random trailers play correctly. However, I’m not sure how to set it up so that when I see a movie trailer I like, I can click on it to watch the full movie directly. Is this feature possible?

With online trailers, I can add the movie to the watchlist and then click to watch the film. But it seems that locally organized trailers don’t have the option to be added to the watch queue.

The option is there in the web app.

Which Plex client type are you using?

Thank you so much for answering my questions; I really appreciate your help. I’m using an iPhone, Apple TV, and other devices. It seems that trailers in the “Movies” category can be added to the watchlist, but the trailers I created in the “Other Videos” section don’t have the “add to watchlist” option. Also, there are 3 more things I’m a bit confused about:

Are trailers in the “TV Shows” section not able to play automatically? I tried, but they don’t seem to play.
When auto-playing trailers, does it only randomly play trailers from one category and not from all directories in the current account?
What I want to achieve is this: I have a lot of movie library files, and I often can’t decide what to watch. I want to organize trailers for all my media files, so when I watch a movie, it randomly plays a few trailers, which might give me additional ideas of what to watch next. However, with the “add to watchlist” feature, it seems like the trailers can only be added to a specific list, and then I have to go through that list to find the movie to play. I haven’t found a more convenient way to use this list when watching on an Apple TV or iPhone. How can I operate this more easily?

This checkbox only exists in a Movies-type of library:

It is trying to replicate a traditional Cinema experience, where you have some trailers running before the main movie.
That doesn’t happen with series.

That’s because the Watchlist requires the video to be “matched”. That means it must exist on the Plex-ingested metadata sources (IMDb, TheMovieDB, TheTVDB) and the item has to be connected to that dataset by being “matched”.
Which doesn’t happen in “Other Videos” libraries.

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