This study examines the role of productive struggle within the Mathematics Success Initiative framework, focusing on selected higher education mathematics courses. Using a qualitative case study design, the research explores how specific instructors implement the tenet of productive struggle in their active learning strategies and its perceived effects on student learning outcomes. Grounded in a constructivist epistemological perspective, the study involved structured, open-ended interviews with instructors and students, alongside classroom observations, to gather detailed insights into their experiences and perceptions. The findings from these cases suggest that in the observed educational settings, some students felt more empowered to engage with challenging mathematical problems, which may have contributed to the development of critical thinking skills and enhanced academic potential. These observations indicate that productive struggle, as implemented in these classrooms, could foster greater student engagement and resilience in tackling complex concepts. The study also identifies specific ways in which productive struggle might facilitate deeper understanding and retention of mathematical concepts, though these outcomes are context-specific and should not be broadly generalized. The research underscores the potential benefits of integrating productive struggle into active learning practices within the observed settings, emphasizing the importance of creating a supportive classroom environment that encourages perseverance.