Context: Questioning is an instructional strategy used by preceptors to assess knowledge and improve clinical reasoning in students. Preceptors face challenges asking high-level questions, and bug-in-ear (BIE) technology may be one way to address these challenges. Objective: Assess the cognitive level of questions asked by preceptors with and without the use of BIE technology. Design: Mixed methods. Setting: Seven clinical education sites affiliated with 3 Commission on Accreditation of Athletic Training Education--accredited undergraduate athletic training programs. Patients or Other Participants: A total of 13 athletic training students and 8 preceptors. Main Outcome Measure(s): Preceptor-student interactions were observed and audio recorded for 2 days without and 2 days with the availability of BIE technology. Cognitive levels of questions were analyzed using the Question Classification Framework and a 2 (Intervention) X 3 (Question Type) analysis of variance. Interviews were conducted to obtain participants' experiences with and perceptions of questioning and BIE technology. Interviews were analyzed by 2 individuals using an inductive coding process. Trustworthiness was established with member-checking, multiple-analyst triangulation, and data-source triangulation. Results: Preceptors asked 1044 questions, including 46.94% low-level (n=557), 2.38% high-level (n=24), and 50.69% other (n=463), such as yes/no questions, during 149 hours of observation. Preceptors asked more questions during the control sessions than when they used BIE technology (39.1 ± 31.7 versus 26.1 ± 20.4 questions; F1[subscript 1,7]=6.3; P=0.04), although participants perceived the opposite. Two themes emerged from the interview data: (1) Preceptors use questioning to develop clinical reasoning in students, and (2) BIE technology facilitates low-level questioning. Conclusions: Although preceptors primarily asked low-level and basic recall questions of their students during clinical education, participants described the use of strategic sequencing of questions to facilitate clinical reasoning. Preceptors should be encouraged to ask more high-level questions and sequence them to target higher cognitive processing. Bug-in-ear technology was not effective at facilitating effective questioning in clinical education.