Objective: To determine information transfer during simulated shift-to-shift intraoperative anesthesia handoffs and the benefits of using a handoff tool. Patients and Methods: Anesthesiology residents and faculty participating in simulation-based education in a simulation center on April 6 and 20, 2017, and April 11 and 25, 2019. We used a fixed clinical scenario to compare information transfer in multiple sequential simulated handoff chains conducted from memory or guided by an electronic medical record generated tool. For each handoff, 25 informational elements were assessed on a discrete 0–2 scale generating a possible information retention score of 50. Time to handoff completion and number of clarifications requested by the receiver were also determined. Results: We assessed 32 handoff chains with up to 4 handoffs per chain. When both groups were combined, the mean information retention score was 31 of 50 (P