Evidence suggests that both pharmacy students and preceptors are struggling in the experiential setting. Underlying this phenomenon is a potential interconnected and cyclic set of behaviors being reinforced between students and preceptors. These behaviors can contribute to or are the result of higher levels of burnout and a decrease in the development of student clinical skills and subsequent performance on rotation. In this review, the authors investigate various challenges commonly encountered in the experiential environment. These challenges can range from an observed decrease in student engagement, motivation, and critical thinking skills to an increase in preceptor burnout and culture shifts in the clinical practice environments. These factors all ultimately impact patient care and overall student performance. For each challenge identified, strategies will be presented that can be implemented by students, preceptors, and pharmacy programs to break the cyclic pattern identified.