The volume of cases that residents perform independentlyhave decreased leaving graduating chief residents less prepared for independent practice. Outcomes are not worse when residents are given autonomy with appropriate supervision, however it is unknown if outcomes are worsening with decreasing operative autonomy experience. We hypothesize that resident autonomous cases parallel the improving outcomes in surgical care over time, however, are less complex and on lower acuity patients. Retrospective study utilizing the Veterans Affairs Surgical Quality Improvement Program (VASQIP) database. Operative cases performed on teaching services within the VASQIP database from July 1, 2004 to September 30, 2019, were included. All adult patients who underwent a surgical procedure from July 1, 2004, to September 30, 2019, at a VA hospital on a service that included residents were initially included. After inclusions and exclusions, there were 1,346,461 cases. Cases were divided into 3 sequential 5 year eras (ERA 1: 2004-2008 n = 415,614, ERA 2: 2009-2013 n = 478,528, and ERA 3: 2014-2019 n = 452,319). The main exposure of interest was level of resident supervision, coded at the time of procedure as: attending primary surgeon (AP); attending and resident (AR), or resident primary with the attending supervising but not scrubbed (RP). We compared 30 day all-cause mortality, composite morbidity, work relative value unit (wRVU), hospital length of stay, and operative time between each ERA for RP cases, as well as within each ERA for RP cases compared to AR and AP cases. There was a progressive decline in the rate of RP cases in each successive ERA (ERA 1: 58,249 (14.0%) vs ERA 2: 47,891 (10.0%) vs ERA 3: 35,352 (7.8%), p < 0.001). For RP cases, patients were progressively getting older (60 yrs [53-71] vs 63 yrs [54-69] vs 66 yrs [57-72], p < 0.001) and sicker (ASA 3 58.7% vs 62.5% vs 66.2% and ASA 4/5 8.4% vs 9.6% vs10.0%, p < 0.001). Odds of mortality decreased in each ERA compared to the previous (aOR 0.71 [0.62-0.80] ERA 2 vs ERA 1 and 0.82 [0.70-0.97] ERA 3 vs ERA 2) as did morbidity (0.77 [0.73-0.82] ERA 2 vs ERA 1 and 0.72 [0.68-0.77] ERA 3 vs ERA 2). Operative and length of stay also decreased while wRVU stayed unchanged. When comparing RP cases to AP and AR within each ERA, RP cases tended to be on younger and healthier patients with a lower wRVU, particularly compared to AR cases. Mortality and morbidity were no different or better in RP compared to AR and AP. Despite resident autonomy decreasing, outcomes in cases where they are afforded autonomy are improving over time. This despite RP cases being on sicker and older patients and performing roughly the same complexity of cases. They also continue to perform no worse than cases with higher levels of supervision. Efforts to increase surgical resident operative autonomy are still needed to improve readiness for independent practice.