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Level 2 charging behavior - Charge station not powered / Ready to charge - ChargePoint - J1772

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I have a 2017 Model S & I have chargepoint stations at work. For years, I would get out of my car, religiously plug the adapter into the vehicle's chargeport and then mess around with authorizing the ChargePoint station. Last step would be for me to plug the tail from the chargepoint into the J1772 adapter I had just put in the car's charge port. This stopped working for me recently. When I would plug it in the light would go out on the chargeport or it would just stay green. Charging at SuperCharges or on my home Tesla wall connector was fine. They changed the behavior recently in a firmware release 2020.16.x.x and after (I think). Now I can no longer do what I used to do. In order to draw a change successfully from the chargepoint after 2020.16.x.x firmware, you need to connect the J1772 to the ChargePoint tail first AND THEN plug it into the Tesla's chargeport. I spent a bunch of time troubleshooting this including testing with a second J1772 adapter. I hope this saves someone else the trouble as there was literally a few weeks when I couldn't charge at work because I am a creature of habit.
 
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I've also ran into this same issue with my 2013 S. Walked away a few times from the chargers at my apartment to check the ChargePoint app and it still saying "starting charge session" for a few minutes. Check the Tesla app and it also stated it hadn't started charging yet. Habit has changed to open charge port, scan phone/watch on the CP station, pull out the plug and attach the J1772 adapter to it, connect to car. Haven't had any issues with that yet!