Oakland the dog is supposed to be learning how to cartwheel with his little friend:
If this were true, it would be a charming example of social learning - something we know dogs are capable of. Dogs do imitate each other, and they can learn to imitate humans, too.
However, dogs don't need to learn to roll over. It's instinctive, a fixed pattern. If anything they need to learn that it's not okay to roll in everything! Oakland isn’t “learning to cartwheel”, he’s doing what comes naturally.
I suspect that the dog is uncomfortable in his shirt, and is rolling over at random. Some dogs are confused by tight shirts, and end up rolling around on the floor.
Here’s my shelter dog friend Cheechoo doing something similar with his Thundershirt:
If anyone’s being cued in this video, it’s the kid, not the dog!