The problem allegedly stems from a buffering bug that apparently causes iTunes to never begin downloading the next song in the queue if it’s shorter than 60 seconds. Basically, iTunes is left waiting for a download to finish that has in fact never started. The bug has been reported to Apple and we expect it to be fixed in a future iTunes update.
According to the post published by MacRumors, when a track that is shorter than 60 seconds is played in its entirety (meaning not skipped at all by the listener), Apple Music’s streaming capabilities will stall on the next track, and it will show up as perpetually buffering.
“It looks like the way AM handles streaming is when the current song is a minute from the end, iTunes signals the next track in the queue to start downloading so that it’s ready to play when the current song is over. However, when the song is less than a minute long the next song’s download is never initiated, apparently because some “one minute remaining†event is never triggered! This means the app just sits waiting for a download to finish that has in fact never started.â€
This issue is not reproducible in macOS Sierra or iOS 9.3.2.