I’ve enabled trailers for movies, selected all of the options (play from the internet, play unwatched movies from my library etc) and the trailers play before a movie as expected (in my case, 3 trailers before each movie). They also seem to respect the setting where it plays trailers appropriate to the rating (my kids movies play G rated trailers).

However, it plays the same trailers over and over. I’ve seen the Charlie Brown trailer at least thirty times. It plays some neat old ones from time to time, I’m fine with that. But it basically plays two trailers of the same movies every time and one random one.

Is this something others are experiencing?

Latest plex pass version of the server and all players, and has existed for several versions.