How can I sync my iPhone listening history with Apple Music?

Are you signed up for Apple Music the service as well? If so there are two paths.

• If not, normally the regular settings in the music app on your phone should allow play counts, etc, to update from phone to computer
• If so, there is an option in settings you need to turn on. I don't know the name of it because I am not signed up for Apple Music and the setting isn't offered up to me on my phone, but the setting has to do with something about sharing data on songs played, etc, with other devices. If this is off, play counts won't update to the PC