Exactly, it's a common failure mode for math/programming-minded people when encountering the law. But the law is not like a compiler, mechanically following some fully-specified set of rules.
The legal system is rather the spiritual successor of the original "system" where a wise Solomon-like elder would adjugate the issue based on their best judgment and intuition and customs, ideally seeking peace and social satisfaction and future harmony. Codified law channels this into some more pre-shaped form, but the fuel of the legal system is still the human judgment and common sense at the core. Often the law basically just prompts and nudges the judgment of the jurors or judge to a certain direction, but it can't account for all corner cases. The nerd mind asks ok ok but what if X, where do you draw the sharp line between X and Y? It doesn't matter. If it comes up, a court will decide it based on all available common sense and the implicit values of the culture.
In the cases where someone seemingly gets away with "rules-lawyering", then it's not purely their genius logic-brain that wins, but there is some kind of slanted playing field that's not really available to you. Of course the line between "annoying rules-lawyering based on literal interpretation of technicalities that obviously nobody intended to be interpreted so" and something that was not anticipated initially but does fit within the rules. This decision itself is based on judgment and intuition. In life, sometimes coming up with a "technically works" thing is rewarded and lauded (math proofs, pathological counterexamples, cracking an encryption library via side-channel attacks), other times you get an eye-roll and that's obviously cheating and wasn't meant (e.g. courts of law and fun at parties).