I'm in All Shows > Recently Updated, and trying to delete some recordings I don't have interest in. For this example, these are TV shows, but there's only one recording in them. When I click and hold their thumbnail, and then choose "Trash all Items," I get the confirmation to "Trash 1 Item" and I choose "Trash all," but then I'm brought back to All Shows > Recently Updated, and that show is still there.
It's not consistent for all shows though. I can't delete the 1 episode of Matlock this way, for example, no matter how many times I try. I can only delete it by going into the show and manually deleting the 1 episode.
I was however able to delete the 1 episode of 227 this way, via "Trash all items." I haven't figured out the rhyme and reason, why some shows let me "Trash all" this way, and some don't.