Background Resident and faculty views of program strengths and opportunities for improvement (OFIs) offer insight into how stakeholders assess key elements of the learning environment. Objective This study sought (1) to assess the degree to which residents and faculty in 359 programs in 5 surgical specialties (obstetrics and gynecology, orthopaedic surgery, otolaryngology, plastic surgery, and surgery) were aligned or divergent in their respective views of program strengths and OFIs; and (2) to evaluate whether responses to selected questions on the Accreditation Council for Graduate Medical Education (ACGME) Resident Survey correlated with strengths or OFIs identified by the residents during the site visit. Methods Faculty and resident lists of program strengths and OFIs in site visit reports for 2012 and 2013 were aggregated, analyzed, and compared to responses on the Resident Survey. Results While there was considerable alignment in resident and faculty perceptions of program strengths and OFIs, some attributes were more important to one or the other group. Collegiality was valued highly by both stakeholder groups. Responses to 2 questions on the ACGME Resident Survey were associated with resident-identified OFIs in site visit reports pertaining to aspects of the didactic program and responsiveness to resident suggestions for improvement. Conclusions The findings offer program leadership additional insight into how 2 key stakeholder groups view elements of the learning environment as program strengths or OFIs and may serve as useful focal areas for ongoing improvement activities.