As the surgical education paradigm transitions to entrustable professional activities, a better understanding of the factors associated with resident entrustability are needed. Previous work has demonstrated intraoperative faculty entrustment to be associated with resident entrustability. However, larger studies are needed to understand if this association is present across various surgical training programs. To assess intraoperative faculty-resident behaviors and determine if faculty entrustment is associated with resident entrustability across 4 university-based surgical training programs. This cross-sectional study was conducted at 4 university-based surgical training programs from October 2018 to May 2022. OpTrust, a validated tool designed to assess both intraoperative faculty entrustment and resident entrustability behaviors independently, was used to assess faculty-resident interactions. A total of 94 faculty and 129 residents were observed. Purposeful sampling was used to create variation in type of operation performed, case difficulty, faculty-resident pairings, faculty experience, and resident training level. Observed resident entrustability scores (scale 1-4, with 4 indicating full entrustability) were compared with reported measures (faculty level, case difficulty, resident postgraduate year [PGY], resident gender, observation month) and observed faculty entrustment scores (scale 1-4, with 4 indicating full entrustment). Path analysis was used to explore direct and indirect effects of the predictors. Associations between resident entrustability and faculty entrustment scores were assessed by pairwise Pearson correlation coefficients. A total of 338 cases were observed. Cases observed were evenly distributed by faculty experience (1-5 years' experience: 67 [20.9%]; 6-14 years' experience: 186 [58%]; ≥15 years' experience: 67 [20.9%]), resident PGY (PGY 1: 28 [8%]; PGY 2: 74 [22%]; PGY 3: 64 [19%]; PGY 4: 40 [12%]; PGY 5: 97 [29%]; ≥PGY 6: 36 [11%]), and resident gender (female: 183 [54%]; male: 154 [46%]). At the univariate level, PGY (mean [SD] resident entrustability score range, 1.44 [0.46] for PGY 1 to 3.24 [0.65] for PGY 6; F = 38.92; P < .001) and faculty entrustment (2.55 [0.86]; R2 = 0.94; P < .001) were significantly associated with resident entrustablity. Path analysis demonstrated that faculty entrustment was associated with resident entrustability and that the association of PGY with resident entrustability was mediated by faculty entrustment at all 4 institutions. Faculty entrustment remained associated with resident entrustability across various surgical training programs. These findings suggest that efforts to develop faculty entrustment behaviors may enhance intraoperative teaching and resident progression by promoting resident entrustability.