Objective: To determine the association between intraoperative entrustment and personality alignment. Summary Background Data: For surgical residents, achieving operative autonomy has become increasingly difficult. The impact of faculty-resident operative interactions in accomplishing this goal is not well understood. We hypothesized that if operative dyads (faculty and resident) had personality alignment or congruency, then resident entrustment in the operating room would increase. Methods: We completed a retrospective analysis of 63 operations performed from September 2015 to August 2016. Operations were scored using OpTrust, a validated tool that assesses progressive entrustment of responsibility to surgical residents in the operating room. All dyads were classified as having congruent or incongruent personality alignment as measured by promotion or prevention orientation using the regulatory focus questionnaire. The association between personality congruence and OpTrust scores was identified using multivariable linear regression. Results: A total of 35 congruent dyads and 28 incongruent dyads were identified. Congruent dyads had a higher percentage of “very difficult” cases (33.3 vs. 7.4%, P ¼ 0.017), female residents (37.1 vs. 14.3%, P ¼ 0.042) and faculty with fewer years of experience (10.4 vs. 14.8%, P ¼ 0.028) than incongruent dyads. In addition to post-graduate year level, dyad congruency was independently associated with a 0.88 increase (95% CI [0.27–1.49], P ¼ 0.006) in OpTrust scores (overall range 2–8), after adjusting for case difficulty, faculty experience, and post-graduate year. Conclusions: Congruent operative dyads are associated with increased operative entrustment as demonstrated by increased OpTrust scores. Developing awareness and strategies for addressing incongruence in personality in the operative dyad is needed.