Every time my Canadian work visa expired I had to drive over the border, enter the US, turn around and drive back to start the new one. The border guards call it “flag-poling” because you do a U turn around the flag pole.
When I went from work visa to permanent resident I had to do it, in January, in Alaska, at -44 degrees and nasty ice on the roads. That border required 30km of driving through no man’s land before I got into Alaska. I asked the Canadian as I was leaving if I could just u turn his building and come back right now, and he was very firm I had to enter the US, even if for just 20 seconds. Nasty drive, but all ok