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If installing 2 L2 40amp chargers(14-50), can you share the same wiring(4/3) coming from a 60 amp breaker?

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That doesn't always work. It doesn't on my car and many others--maybe mostly the older ones? On mine, if that handle is released, the charge port INSTANTLY locks the adapter in again, and then it won't come out with the handle. Some other cars will keep the port unlocked for a few extra seconds, so then your method can possibly work.

So people recommend the two-hand method because it's foolproof. It always works for all cars all the time. They don't want to recommend some procedure to someone that won't work.

I just went out to the car (2020 M3 SR+, Dec 2019 delivery) to double-check what it's doing. Since it is just above freezing at the moment, the port unlocked as soon as my phone key connected and before I even touched the car!

I initiated charging from the app so it would latch, and was able to release and remove it with a single click/release a few times. I have scheduled charging set up for evening hours, so it wouldn't have tried to start charging right away when I released the button. I'll have to test it again the next time it's charging and see if it makes a difference whether it wants to begin charging when the cord is connected.

Could it also depend on differences between the EVSEs rather than the cars?