Context: Preceptors play an integral role in training athletic training students (ATSs). Balancing roles as health care providers and educators can often be challenging. Role strain is a documented concern for the preceptor, yet limited information is available regarding other issues faced while supervising ATSs. Objective: To explore preceptor challenges. Design: Qualitative study. Setting: Athletic training programs. Patients or Other Participants: A total of 41 preceptors from 2 different data collection procedures (cohorts) participated in the study. Preceptors had an average of 6 ± 2 years (cohort 1) and 5 ± 3 (cohort 2) years of experience as clinical educators, respectively. The preceptors were distributed between college (25) and secondary school (16) settings. Data Collection and Analysis: Data were collected via telephone interviews (cohort 1) and asynchronous online interviews using Question Pro (cohort 2). We used a combination of grounded theory and inductive procedures for data analysis. Credibility of the data was established by investigator and data analyst triangulation in addition to peer review. Results: Role strain was reported by preceptors as they attempted to balance their responsibilities as health care providers and clinical educators. Working conditions characterized by long hours, high patient volumes, and inadequate compensation hindered preceptors' ability to foster a positive learning environment. Because of contrasting personalities and different expectations, some preceptors experienced challenges interacting with students. Conclusions: The preceptor position involves meeting the high standards for education and health care simultaneously. Preceptor training does not often address the challenges of balancing multiple roles. It therefore becomes important for ATSs and preceptors to develop strong lines of communication and determine an appropriate schedule for educational activities. Clinical coordinators should consider both the personalities of preceptors and ATSs and the workload of the preceptor when determining clinical assignments.