Back in 2006 I bought a semi truck to haul hay bales on my farm in Saskatchewan, Canada. I didn't have a Class 1A license yet (I think it's Class A in the US) that would allow me to drive a semi legally but I did it anyway. I had planned to take a course to get it that fall but figured I could get away with it for the summer. My neighbor's done it for many years without a problem.
Well, three months after getting the truck I'm crossing the Trans-Canada highway with a load. I'm pulling a 48-foot trailer loaded with a load of large round hay bales. Now, it's common for us farmers to haul hay unsecured (without straps) as it's often a short haul (for me about 10 miles) and figure we'll get a few more loads done without taking the time to strap them down.
You can guess what happened I'm sure. I got caught as I crossed the highway. Here I am without a proper license and an unsecured load. I figure I'm in for a significant fine. I play it cool. I'm respectful of the DOT officers but don't admit anything except the obvious which is the unsecured load, the reason they had stopped me. They also asked if I had a permit for an oversize load (I was 10 feet wide the way we load hay) and there was some concern over that but I was not travelling down a highway, only crossing them. They would look into that now. They go back to the car to write it up and call in my name and truck plate. I wasn't carrying my drivers license that day so they didn't know right away that I was only qualified for Class 5 (regular 4-wheel cars and trucks). Well, they come back and ask me what I'm doing driving a semi with only a Class 5. I admitted that yes I was cheating.
OK, here I am without a proper license, an unsecured load and no overdimension permit. How much worse could it get? Well, I lucked out this time. In the end I'm only charged with driving without an appropriate licence which carried a fine of $140Cdn, which they informed me was a lesser fine than an unsecured load fine. And I guess since I wasn't travelling down a highway they couldn't get me for not having a permit. I had the leave the truck there (only a couple of miles from home anyway) with a warning that if they caught me driving it again, they would impound it. We did sneak back after dark and get it home, but it did sit at home until I got my 1A that fall. Oh, and I throw a few straps over now, too, when I'm crossing a highway.
I think it helped that we were respectful of each other and I'm sure having farm plates on the truck and trailer helped, too. Law enforcement is usually are a little less strict with farmers.