Video games are failure-rich spaces that provide a unique lens into how individuals react to failure in challenging environments. In this study, we utilize Cuphead, a notoriously challenging video game to demonstrate a unique behaviorally driven approach to understanding how an individual reacts to failure. Using measures of mastery orientation and data-driven retrospective interviews, we show that individuals who exhibit more mastery-oriented behaviors and more mastery-oriented behaviors before a helpless-behavior are more likely to show a higher game mastery orientation score, and that individuals that abandon a level before completion are more likely to show a lower game mastery orientation score. This introduces video games as a fruitful environment for understanding mastery orientation, a behaviorally driven approach to understanding how individuals react to failure, and provides a glimpse into how individuals react to failure in a challenging video game.