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Auto-start Live Track doesn't automatically start Live Track...

So, I've experienced this a few times...

My phone is connected to my device, Garmin connect sees the phone, I start my activity, but Live Track session doesn't start. Sometimes it will start at some random point during my ride, but sometimes it just doesn't start at all.

I've confirmed that AutoStart is enabled. I know that if I disable it, I can manually start/stop Live Track just fine (meaning it works).

I know my phone & device are connected, that garmin connect (updated yesterday, but this is not new behavior) is running, and that my phone had a data connection. I know this because I can see my ridding buddies just fine on the Group Track screen. They just don't see me; because Live Track isn't started. 

Any ideas??