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Charging connector lock timing

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I just got a model Y with the wall connector and the charging cable lock is confusing me. After charging is complete, I push the button and pull. It's locked. After a few seconds, I hear some sounds like the car is booting up, but the lock doesn't release, so I push the button again. The green light comes on like it's trying to charge again. I press the button again and hear a click, but it's still locked. It takes about 6-8 tries to get the cable out. Then, when I get in the car, I see an error message telling me I'm charging too often

There must be some kind of secret handshake, but I haven't figured it out yet
 
See Tesla Model Y Owner's Manual, Page 159: https://www.tesla.com/sites/default/files/model_y_owners_manual_north_america_en.pdf

The button on the charging connector opens the charging port. To unlock the charging port to remove the charging connector press and hold the button. (The light on the charging port will change from green or blue to white when the charging port is open and unlocked.)

You can start and stop charging from the Charging screen in the Tesla vehicle or from the Tesla app. Once you have stopped charging you can unlock the charging port and remove the charging connector from the charging port.

For daily charging do not charge beyond 90% state of charge (SOC).

Tap the number to the left of the battery icon to switch between estimated range and % SOC. (Else, the battery indicator can be set to display % SOC or estimated range within the Display Settings.)

Charge Port Light

WHITE: The charge port door is open. Model Y is
ready to charge and the connector is not inserted, or
the charge port latch is unlocked and the connector
is ready to be removed.

BLUE: Model Y detects that a connector has been
plugged in.

BLINKING BLUE: Model Y is communicating with the
connector. Either Model Y is preparing to charge, or a
charging session is scheduled to begin at a specified future time.

BLINKING GREEN: Charging is in progress. As Model Y approaches a full charge, the frequency of the
blinking slows.

SOLID GREEN: Charging is complete.

SOLID AMBER: The connector is not fully plugged in.
Realign the connector to the charge port and insert
fully.

BLINKING AMBER: Model Y is charging at a reduced
current (AC charging only).

RED: A fault is detected and charging has stopped.
Check the touchscreen for a fault message
 
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@MPME you are not alone! I found that very confusing for the first couple of months--sometimes it was fine (car was already awake) and other times I'd tap the button and start to pull only to find it still locked. As @jcanoe and @boulder.dude have mentioned, the solution is to either wake the vehicle (using app or door handle) or just press and HOLD the button until the T logo inside the connector goes white, then pull and then release the button. This is the method I use most now that I've gotten the hang of it.
 
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