Background <p>Preoperative assessment is a key but inconsistently taught skill in internal medicine residency, particularly in the ambulatory setting. Many residents report low confidence and limited formal training.</p> Objective <p>To evaluate the impact of a structured, gamified Jigsaw-based workshop on internal medicine residents’ knowledge acquisition and self-reported confidence in preoperative assessment.</p> Methods <p>In 2025, we conducted a quasi-experimental pilot study at the University of California, San Diego. Primary Care Track residents (intervention group) completed a three-hour interactive Jigsaw workshop on four domains of preoperative management: cardiovascular risk, medication management, anticoagulation, and considerations for special populations. Residents in the control group received standard residency training in preoperative medicine through routine clinical exposure during inpatient rotations (wards, intensive care unit, and consult services) and outpatient settings, including continuity clinic and ambulatory electives. Additional instruction occurred through the residency’s protected didactic curriculum, including Wednesday School and Friday School, four-hour conference blocks covering rotating internal medicine topics. Preoperative assessment was addressed within this broader curriculum but not through a dedicated standardized program. Pre- and post-surveys assessed knowledge (multiple-choice) and confidence (Likert scale). Due to the small sample size, formal hypothesis testing with p-values was not performed. Instead, effect sizes were calculated to estimate the magnitude of differences between the intervention and control groups.</p> Results <p>A needs assessment of 159 residents (12% response) revealed low confidence in perioperative care; over half reported no structured training. In the control group (<i>n</i> = 11 pre, <i>n</i> = 10 post), notable gains are observed in special population (40% to 49%, effect size = 0.45) and anticoagulation (41.1% to 48.50%, effect size = 2.00). Cardiovascular risk and medical management remain stable (45.40% to 39.40%, effect size = 0.18, and 60.60% to 56.1%, effect size = 0.04, respectively). In the intervention group (<i>n</i> = 11, <i>n</i> = 10 post), all categories show notable gains, with special populations and cardiovascular risk reaching statistical significance: cardiovascular risk group (37.50% to 66.70%, effect size = 4.04), medication management (64.5% to 75%, effect size = 0.45), special population (45% to 95%, effect size = 4.26), and anticoagulation (45.80% to 58.30%, effect size = 0.42). In the control group (<i>n</i> = 11 pre, <i>n</i> = 10 post), mean confidence scores remained largely unchanged, with minimal effect (2.35 vs 2.38; effect size = 0.10). In contrast, the intervention group (<i>n</i> = 8 pre, <i>n</i> = 8 post) demonstrated substantial improvements in confidence across all domains following the workshop, with mean Likert scores increasing from 1.86 to 3.18 (effect size = 2.48). Qualitative feedback showed that residents valued the interactive, case-based format and the gamified “Escape the OR” activity.</p> Conclusions <p>A single Jigsaw-based workshop integrated into a primary care residency curriculum was observed to be associated with improvements in resident knowledge and confidence in perioperative assessment. These early findings suggest that structured, interactive workshops may help address gaps in perioperative education and support further evaluation of learner-centered instructional strategies in larger training settings.</p>