Over the last few months I was having intermittent issues when using CarPlay and I chalked it up to: because Land Rover.

However, I just completed a 2k mile round trip to Savannah and back by myself. Had lots of opportunities to observe these quirks.
Quirk one: Pandora would play one or two songs and then stop. If I unplugged the phone and plugged back in it would play one or two more and stop again.
Quirk two: Related to the above, but would have similar issues playing iTunes music that wasn't already downloaded.
Quirk three: Waze would occasionally say that it couldn't connect to the network even though my phone had several bars of reception. When I unplugged the phone, it was able to connect.

Through lots of staring and thinking, I realized that the issue was the VPN I'd installed on my phone a couple of months ago (I use FYD). Somehow it was causing communication errors with the apps above, probably due to location settings. When I disabled the VPN, everything worked smoothly from then on.

Just an FYI for anyone using a VPN for privacy, etc.

 

I use a VPN and sometimes forget to disconnect and I do experience more problems when using it then not. Not that the VPN is unreliable, simply that it takes a while for it to notice that the underlying connection has dropped and for it to then re-negotiate a new tunnel connection when the underlying connection comes back.
If your phone loses or he a very bad data connection as you’re driving around due to buildings or whatever this can happen more frequently than you might imagine. It has nothing to do with CarPlay itself. My wife in the passenger seat using her phone normally as I was driving noticed the problem and I trained my phone which was hooked up to CarPlay also be hard better without the VPN when on the move.