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Today's academic and social environment creates uncertainties, new roles, frequent changes, and challenging situations for student affairs academic leaders. The purpose of this study was to explore how student affairs academic leaders described their recent challenging experiences in addressing student drug abuse in higher education. The conceptual framework was based on adult transformative learning theory and applied transformative leadership perspectives. An interview format with open-ended questions was used to explore the experiences of 8 student affairs leaders who had faced challenging situations in the context of student drug abuse. A qualitative interpretive analysis was used that involved open coding of significant words and statements that were further classified into themes. Results from the leaders' experiences indicated 4 themes associated with transformative learning: challenge, reflection, constructive dialogue, and action, as well as 7 themes related to transformative leadership: accurate information, collaboration, constructive dialogue, critical reflection, responsibility, support, and vision. Critical reflection and vision were also found to have aided leaders faced with challenging situations. A significant finding was that all participant leaders asserted the importance of applying evidence-based research in the hope of developing positive action for both the students' well-being and the growth of the academic institution. The results of this study have the potential to inform best practice in adult transformative learning and adult transformative leadership, benefiting academic leaders facing challenging situations in their social and academic environments.