To reap the rewards of expertise and forego its constraints, scholars suggest we must manage the depth and breadth of our experience. In this study, we draw on forty years (1982-2022) of general aviation accident investigations to examine the effect of domain-specific experience on individuals’ performance in crisis – moments of acute need where swift and creative decisions are necessary to thwart catastrophe. Our analyses unfold in two parts. First, we predicted and found evidence of a curvilinear association between a pilot’s degree of specialization (i.e., the share of total flight hours spent flying a specific aircraft) and performance in crisis such that the accumulation of domain-specific experience generally reduced the odds of fatal injuries and severe damage, except among pilots with highly concentrated experience. Second, we probed the underlying mechanisms and boundary conditions of specialization’s effect on pilots’ performance. Contrary to our expectations, we found evidence that the cost of domain-specific experience revealed in part one diminished in dynamic, domain-adjacent conditions (e.g., poor weather conditions) that forced pilots to draw on their knowledge in an unfamiliar or unusual context, challenging prevailing theory about domain-relevant context as a conditioning factor in the performance effects of experience. In doing so, this paper contributes to the literature on expertise and research about crisis leadership, suggesting that organizations could benefit from strategies that manage the depth and breadth of individuals’ experiences. It also contributes to broader policy discussions about pilot experience and training requirements.