re: Has anyone had issues crossing Canadian border with dwi (or pending) on record?

Detroit to Windsor and say your going to a casino. If you do go to a casino don't bring anything over $10k back or US customs will make life hell. Idk why our southern border isn't protected as well. Well actually I do

Drove across the border from Vermont last October and the agent asked a bunch of questions (Where are you going, why and for how long? Any drugs, guns, etc.? She also asked if we had ever been in front of a judge. We said no, not sure if she ran our background or anything but she sent us on our way pretty quick. We came back through some podunk crossing into the US and that dude couldn't have given 2 shits and basically waved us on through.

I went to Canada on a duck hunting trip in October. We did Minneapolis into Saskatoon, Saskatchewan. I bet 90% of the flight was duck hunters. When I got to security the dude asked me if I had any prior arrests. It kinda hit me by surprise because I have been cleared with security clearances in my career so kinda forgot I did get a DWI right out of high school about 30 years ago along with a simple battery about the same time for hitting a dude that took a swing at me in a bar. The DWI was later dropped and isn’t on my record although if you dig deep on me you can find the arrest (I did this deep dive on myself so I know) and obviously the battery charge. One of the guys in my group who was ahead of me at security is a Senior Agent with the DEA and we have been friends since grade school so he knows my history was watching this interaction go down and he was watching the security guard. He told me the security guard already had my info pulled up on his screen from my passport. I admitted the simple battery arrest but was sweating the DWI arrest and he cleared me.

Moral of the story is assume they already know when you get there.