If your Canadian insurance has expired, would that mean your registration has expired too, and if that is the case, would any company give you any sort of liability insurance and even if they did, I would be checking the fine print with a powerful magnifying glass to make sure they honour the policy.
As an example, Lots and lots of BC registered cars end up below the border because BC makes it very easy for anyone to buy and insure the vehicle in the first place even if they are not Canadian, but then they make it just about impossible to sell or re-register the vehicle unless you are actually in BC. So those vehicles get lent to the next "owner" who don't really own it and merely borrow the vehicle using the authorisation of a Poder.
Not sure what happens to them all but there must be a big pile rusting away somewhere in South America. Maybe they sneak back across the USA and then into Canada and sort out the paperwork, or maybe they just walk away from them and fly home
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