Fade between songs not working in Music with airplay

I'm running a playlist on Apple Music on a MacBook Pro and figured out that crossfade only works if you're not streaming using Airplay. Can't see why it doesn't work as whatever comes out of your computer speakers should be reproduced with Airplay.

Further more, even on the computer speakers alone, sometimes it works, sometimes it doesn't. I've even tried on multiple computers.

Does anyone know why this is happening?