This paper highlights the importance of designing failure paired with feedback within puzzles. Using vignettes from players? gameplay, it discusses how players? approaches to solving puzzles informed the iterative design of game mechanics of Hello New World, a videogame created to promote youth participation in cybersecurity. Preliminary findings suggest well- designed failure and feedback creates productive frustration that supports players in learning, whereas poorly designed feedback creates unproductive frustration which inhibits the gameplay and learning experience.