Playlist Does Not Repeat... Why?!

I have two different playlists (one for studying, one when I sleep) that each contain only 1 song which I like to listen to on an endless repeat. On Spotify, this was not an issue. However, I recently purchased two Apple HomePods and along with that, I switched back to Apple Music. On Apple Music, I cannot seem to get these playlists to repeat! It doesn't seem to matter whether I am using Siri and trying to play it on a HomePod or using the Music app on my iMac—neither wants to repeat. I have tried repeat 1, repeat all, and shuffle. Can anyone help me? This is beyond frustrating. It should be very simple. Why doesn't it work?!