There are a number of little bugs in iTunes 12.4, the latest version of Apple’s media manager and player. One that has come to light is the fact that the Crossfade Songs feature is broken. When this feature is active, iTunes segues songs, using a user-configurable amount of time for the cross fade.
I’ve gotten lots of reports from readers about this, and I can confirm that it doesn’t work for me. This is clearly a bug, and I’m sure Apple will fix it soon. But if you’re used to using the Crossfade Songs feature, and it’s not working, you should know that it’s not you; it seems to be happening to everyone.