Use tracks with lots of obstacles, gutters and hills. Try turning sideways into them. The handbrake, activated with
helps a lot. Use this to quickly initiate a drift. Typially this drift starter is used to quickly turn the vehicle and redirect torque, while also giving it great deceleration. If you use it while headed towards a hill it can be a great way to get some sideways air. The gutters on the sides of some roads are a good way to start turning the vehicle. Use a starter like that and then a rock or hill to generate more flipping force. Hill patterns are very complicated. If you can use just those, then go for it. That's how I got this achievement. It was part luck. I flipped onto a little embankment with a hill leading up to higher ground with a good angle and did a roll. I rolled the vehicle along the longitudinal axes that goes from the bumper and trunk to the hood and did a front roll too. I also performed some other rolls in the Career and other Quick Race tracks.