The Accreditation Council for Graduate Medical Education work rules have forced programs to critically appraise the overall educational value (OEV) of rotations. Successful rotations must satisfy Residency Review Committee mandates and optimize the service-to-education ratio (SER). This study was designed to examine the relationship between the OEV and SER and identify rotation characteristics (RC) associated with both. The Division of Surgery Education at the Hospital of the University of Pennsylvania administered a survey in FY2011 to all residents detailing resident perceptions regarding OEV, SER, and other RC. Responses were linked to additional rotation data. The relationship between OEV and SER was examined before and after controlling for significant RC identified in univariate analyses. Subgroup analyses by junior (CY1-2) and senior (CY3-5) resident status were performed. The survey was sent to 85 residents participating in 48 general surgery rotations, with an overall response rate of 87%. OEV was inversely proportional to SER. All RC were significant predictors of OEV in univariate models except rotation length, patient care participation and the presence of fellows. SER alone was a significant predictor of OEV (coefficient = −1.24, p < 0.001) and explained 68% of the variation in OEV. After including other RC, SER remained a significant predictor (coefficient = −1.08, p < 0.001) and the model explained 85% of the variation in OEV. In subgroup analysis, SER remained a significant predictor of OEV for junior residents (coefficient = −1.27, p = < 0.001), but not for senior residents (coefficient = −0.46, p = 0.15). The SER is inversely correlated with the OEV of general surgery rotations for the aggregate group of surgical residents, but this relationship appears to be attenuated by other factors in the senior resident group. Identification of the factors that affect junior surgical residents may provide the ability to improve the SER for junior residents and allow for significant improvements in perceived OEV for the resident body as a whole.