I’ve run into this issue before. Disabling the native Safari content blocker for the Plex web app resolved it for me.[edit: I stand corrected… still not working with Discover trailers; just for trailers on my own libraries]
@lacer : can you verify this is disabled in the website preferences of Safari?
Thanks for reporting. This does appear to be isolated to trailers hosted by Plex (Discover or Movies & TV Shows) and Safari while using app.plex.tv or the bundled web app on your PMS. Local PMS trailers are working as expected. I changed the tag on this post to better reflect this. An internal issue has been filed. Thanks again for reporting!