I don't know the solution to this either. Worked flawlessly for me (connected automatically every time) for like the first 18 months I owned the car, then it got weird. For me, it stopped working mostly when I started up the car at home. And I think that is because CarPlay works thru WiFi and my phone was having a hard time disconnecting from my home WiFi and then connecting to my Car Wifi. I feel like things started to get bad after switching to iOs 13. So now, when I leave the house, after I get a couple of hundred yards away, I manually connect the device. I think if you wait a long while it might eventually connect. But of course we need it to connect to use the phone, etc, thru CarPlay. Annoying.
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