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The design of most learning environments focuses on supporting students in making, constructing, and putting together projects on and off the screen, with much less attention paid to the many issues—problems, bugs, or traps—that students invariably encounter along the way. In this symposium, we present different theoretical and disciplinary perspectives on understanding how learners engage in debugging applications on and off screen, examine learners’ mindsets about debugging from middle school to college students and teachers, and present pedagogical approaches that promote strategies for debugging problems, even having learners themselves design problems for others. We contend that learning to identify and fix problems—debug, troubleshoot, or get unstuck—in completing projects provides a productive space in which to explore multiple theoretical perspectives that can contribute to our understanding of learning and teaching critical strategies for dealing with challenges in learning activities and environments.