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Upload Insurance Without VIN? Huh?

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In Nevada I just showed them a copy of my current insurance when I picked up the car and was GTG - never uploaded anything. Didn't need to provide copy with Tesla with VIN as it states on their website. I am covered on any car I drive and any new car for 30 days per my policy.
 
In Ontario. Have a VIN from the SA, but it's not listed in my account page.

Attempted to register for insurance and the company will not proceed until the VIN is registered with the provincial authorities. That seems unlikely being as it's still probably on a truck in the US somewhere. They probably don't register them until they're taken off the truck and inspected.

Googling around, seems pretty common with Tesla that you only really can get the insurance a day or so before delivery.

Combine that with the possibility that Tesla will swap VINs on you at the last minute, and seems like a somewhat chaotic process.
I'm with TD Meloche Monnex in Ontario. I called the morning of pickup and got insurance. They couldn't see the VIN in the system but they put it through anyways as they say with new vehicles it can take a while for the VIN to get pushed through. My plates were ready to go when I picked up the car at 14:00 so I guess it was already registered with the province.
 
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Someone from Tesla here in MA called me last night to move my delivery from the 14th to the 12th. He mentioned that the one thing not complete on my account was insurance and asked if I could please complete that. I mentioned that my insurance doesn't want to add the VIN to my policy until I have the car yadda yadda. He told me to just upload proof of insurance on my current car as Dedham will contact my insurance company on delivery day and take care of the rest when it comes to the Tesla which makes sense. They still have proof of insurance before I take delivery that way