Purpose: Otoscopy is a difficult, but requisite skill for Pediatric Residents and Medical Students to master. Locating the tympanic membrane, identifying normal anatomy and characterizing pathology are all skills that have historically been taught with verbal descriptions and/or static images due to the inability of the teacher and learner to perform the physical exam concurrently. Digital Otoscopy using a hand-held smart phone and performed by an Attending/Resident team may facilitate increased learner comfort with the procedure and increased ability to identify pathologic states. Methods: The digital otoscope consists of a smart phone with an otoscope attached directly to the camera lens. The device projects an image of the tympanic membrane onto the smart phone screen. IRB approval was obtained. Residents and medical students (“learners”) rotating at an outpatient resident-run clinic were asked to take a survey and quiz before and after their rotation. The quiz evaluated the learners’ objective ability to answer questions relating to the middle ear in the domains of anatomy, pathology and treatment. The survey assessed the learners’ self-reported comfort performing otoscopy and identifying pathology. The digital otoscope was made available to the Intervention group while the Control group retained access to standard non-digital otoscopes. The change in quiz scores, change in self-reported comfort and change in self-reported proficiency was calculated for each individual learner before versus after their rotation. The 95% confidence intervals were calculated for the intervention and control groups. Results: The learners who utilized digital otoscopy showed a statistically significant increase in quiz scores, 95% CI [0.04, 0.24], a statistically significant increase in self-reported comfort identifying pathology, 95% CI [0.03, 0.37] and a trend towards increased self-reported comfort performing otoscopy, 95% CI [-0.01, 0.21]. The control group showed a trend towards increasing quiz scores, 95% CI [-0.04, 0.20], no significant change in self-reported comfort identifying pathology, 95% CI [-0.22, 0.22], and no significant change in self-reported comfort performing otoscopy [-0.19, 0.23]. There were unmeasured reports of increased Parent and Patient satisfaction. Conclusion: Digital Otoscopy may be a useful tool for Pediatric Residents and Medical Students. Learners utilizing the digital otoscope showed objective improvement in quiz scores as well as subjective improvement in self-reported comfort identifying pathology. Similar improvements were not observed in the control group.