I reported the same thing a long time ago, and then it was fixed fairly quickly and has worked up until just a few server versions ago (I noticed it last week, not sure when exactly it broke again).
The problem is that if I create a smart playlist via the custom filters on the web client, the playlist will work fine, updating itself and everything. But it will have no picture. Not on the web, and not in any other client either. It doesn’t mater if if I enter the playlist multiple times or anything. it gets no picture.
Please fix this, as it’s pretty distracting. And in clients like PlexAmp you start the playlist by clicking on air.
In case it matters, I filter by “artist genre” contains X and track rating is above 2. Thanks.
I still have the same issue - at least for TV show playlists with custom filters. Movies show thumbnails on the smart playlist icon, but none of my TV show playlists show anything but a gray square. Server version 1.14.0.5470.