My new 07 Miata is the first vehicle I've owned in a while that cared about octane. The last one, a Moto Guzzi from the 80s, was a real octane junkie. I learned with that bike that octane numbers at the pump didn't necessarily correspond to how the gas performed in my engine. I don't think it was due to bad labeling, just the fact detonation resistance of different fuels can stack up differently in different engines. I also found that the octane requirement changed quite a bit with temperature, and that low-octane gas + a certain additive (toluene, I think) worked out better than most pump hi-test.
With the Guzzi, there was no doubt about when octane was lacking, so it was easy to dial in just the right mix. With a modern car and its knock sensors, it might not be so obvious. I wonder it an OBD-based monitor ( like