Background Handoffs are a complex procedure whose success relies on mutual discussion rather than simple information transfer. Particularly among trainees, handoffs present major opportunities for medical error. Previous research has explored best practices and pitfalls in general handoff education but has not discussed barriers specific to anesthesiology residents. This study characterizes the experiences of residents in anesthesiology as they learn handoff technique in order to inform strategies for teaching this important component of perioperative care. Methods: In 2016, we conducted a semi-structured interview study of 30 anesthesia residents across all three postgraduate years at a major academic hospital. Interviews were coded by two coders using a grounded theory approach and an iterative process designed to enhance reliability and validity. Results Residents cited lack of consistency as a major impediment to proper handoff education. They found the impact of lectures and written materials to be limited. The level of guidance and direction they received from one-to-one attendings was described as highly variable. Residents’ comfort in executing handoffs was heavily dependent on location and situation. They felt that coordination among the parties involved in the handoff was difficult to achieve, causing confusion about the importance of handoffs as well as proper protocol. Finally, residents offered opinions on when handoff education should occur during the residency and had several recommendations for its improving, including standardization of key handoff topics. Conclusions In a single center study of anesthesiology resident handoff education, residents exhibited confusion related to a perceived disconnect between the stated importance of effective handoffs and a lack of consensus on proper handoff technique. Standardization of curriculum and framing expectations has the potential to enhance resident handoff training in academic anesthesia departments. Electronic supplementary material The online version of this article (10.1186/s12909-018-1387-8) contains supplementary material, which is available to authorized users.