If you haven’t done so already, you’ll need to manually trigger a media analysis on the media items. When I do it, I generally start it at the show-level: Show name -> More button -> Analyze. I’m pretty sure this can be done at the season or episode levels as well, but I’ve not tested that. In my case, this starts the Plex Commercial Skipper silently in the background; no activity is shown in Plex web, the only way I know it’s running is to check my Mac’s activity monitor.