first. my current dog learned to deal with this as a puppy. I was astonished. My last dog I was trying to train the concept her whole life. Never saw a dog be able to handle it before but at this point if my current dog starts to go on the other side of an obstruction I say this way and she immediately corrects. For some reason for all other dogs I find they instinctively want to go the wrong way. So its not even random, they think wrapping more is the way to go. As for humans:
"The Greatest Shortcoming of the Human Race Is Man’s Inability To Understand the Exponential Function"