My brother was driving down from Northern Michigan and his car broke down in Port Windsor I believe. Anyway, I went down with tow chains to tow him back to New York.
We got to the NY border and the Canadian authorities were trying to sort out our situation before we crossed.
At the time, I was living in Michigan, I had a NY driver's license and the car was registered in Indiana. My brother was living in Pennsylvania, Had NY driver's license and was missing some paperwork on the car we were now towing.
The border authorities kept questioning us and didn't like the story and/or couldn't follow why so many states were involved. Eventually, after trying to run through it multiple times, they gave up and just waived us through out of sheer annoyance. Would never happen today...