Purpose: This retrospective study sought to describe (1) progress toward implementation of programmatic assessment in the Core Entrustable Professional Activities for Entering Residency (Core EPA) pilot and (2) changes in entrustment decision-making outcomes, between initial attempt at entrustment decision making for the graduating class of 2019 and the second entrustment decision-making cycle for the graduating class of 2020. Approach/Methods: Four Core EPA pilot schools introduced EPAs frameworks and tested entrustment decision-making processes on a formative basis (for program evaluation purposes only) for some or all students in their 2019 and 2020 graduating classes. 1–4 Schools considered the same EPAs (4–13 per school) in each year. 4 For each EPA considered, a trained entrustment group (TEG) made an entrustment determination (“progression away from readiness,” “progression toward readiness,” “ready to be entrusted,” or “indeterminate” [no entrustment decision made]) for each student and recorded the number of workplace-based assessments (WBAs) available for review. With institutional review board approval or exempt determination by the Association of American Medical Colleges (AAMC) and each participating school, individual-level data were de-identified and merged into a multischool database. We used the chi-square tests to analyze between-group differences (2-sided P < .05 considered significant). Results: The 4 schools made 4,525 (2019: 2,296; 2020: 2,229) EPA-specific entrustment determinations for 732 students (2019: 349; 2020: 383). The proportion of all 4,525 entrustment determinations that were entrustment decisions (including decisions of “progression away from readiness,” “progression toward readiness,” and “ready to be entrusted”) increased (P < .001) from 75% (1,731/2,296) in 2019 to 90% (2,010/2,229) in 2020. These proportions varied on an EPA-specific basis from 20% to 83% in 2019 and from 62% to 99% in 2020 (data not shown), increasing from 2019 to 2020 for all EPAs (each P < .05, data not shown) except EPA 8 (handovers: 93/125 [74%] vs 99/127 [78%]; P = .508) and EPA 12 (procedures: 129/229 [56%] vs 142/228 [62%]; P = .196). The proportion of all 4,525 determinations that were “ready for indirect supervision” decisions increased (P < .001) from 43% (997/2,296) in 2019 to 60% (1,340/2,229) in 2020. These proportions also varied on an EPA-specific basis from 0% to 75% in 2019 and 0% to 93% in 2020 and increased (each P < .001) from 2019 to 2020 for each of EPA 1 (history and physical: 184/349 [53%] vs 334/383 [87%]), EPA 2 (differential diagnosis: 41/100 [41%] vs 59/82 [72%]), EPA 3 (recommend/interpret tests: 22/100 [22%] vs 58/82 [71%]), EPA 6 (oral presentation: 210/324 [65%] vs 315/338 [93%]), and EPA 12 (104/229 [45%] vs 141/228 [62%]). Proportions remained unchanged (each P >.05) for EPA 4 (orders: 9/100 [9%] vs 6/82 [7%]), EPA 5 (documentation: 131/204 [64%] vs 152/224 [68%]), EPA 7 (evidence-based medicine: 164/220 [75%] vs 144/196 [73%]), EPA 8 (9/125 [7%] vs 12/127 [9%]), EPA 9 (collaboration: 120/220 [55%] vs 116/196 [59%]), EPA 10 (urgent care: 2/100 [2%] vs 3/82 [4%]), EPA 11 (informed consent: 1/100 [1%] vs 0/82 [0%]), and EPA 13 (safety: 0/125 [0%] vs 0/127 [0%]). The proportion of all 4,525 determinations for which there were ≥4 WBAs available to the TEG in making their determinations increased (P < .001) from 20% (452/2,295) in 2019 to 42% (938/2,229) in 2020. EPA-specific proportions varied from 0% to 76% in 2019 and 0%–91% in 2020 and increased from 2019 to 2020 for EPAs 1–3, 5–7, 9, and 12 (each P < .001, data not shown) but not for EPAs 4, 8, 10, 11, and 13 (each P > .05, data not shown). Discussion: Proportions of determinations that were entrustment decisions, proportions of determinations that were “ready for entrustment” decisions, and proportions of learners with ≥4 WBAs all increased overall in 2020 vs 2019, and on an EPA-specific basis for EPAs 1–3 and 6. We also observed proportional increases in 2 of these 3 measures for EPAs 5, 7, 9, and 12. In contrast, determinations for EPAs 4, 8, 10, 11, and 13 remained challenging as WBAs availability did not increase and, although more entrustment decisions were made for EPAs 4, 10, 11, and 13 in 2020 vs 2019, <10% of learners were deemed ready for entrustment in each of these 4 EPAs in either year. Acknowledgments: The authors wish to thank Alison Whelan, MD, Chris Hanley, and Beatrice Schmider, all at the Association of American Medical Colleges (AAMC), and all of the members of the Core Entrustable Professional Activities for Entering Residency (Core EPAs) pilot for their support, inspiration, and contributions to the work that led to this report. All participating Core EPA pilot institutions and individuals can be found at https://www.aamc.org/initiatives/coreepas/pilotparticipants/.