While using the Android TV client on my various Shield TVs, I've found that from both the library, but more specifically the "recordings" tab require me to trash the same recordings multiple times.
I'll click the Trash button and it appears that it's gone away, but when I scroll down and back up, it's re-appeared again. SOMETIMES it goes away after going to the trash the second time, but most always goes away after the third try.
I should note that this does not appear to be an issue on my Apple TV 4K.