Background: Faculty entrustment decisions affect resident entrustability behaviors and surgical autonomy. The relationship between entrustability and autonomy is not well understood. This pilot study explores that relationship. Methods: 108 case observations were completed. Entrustment behaviors were rated using OpTrust. Residents completed a Zwisch self-assessment to measure surgical autonomy. Resident perceived autonomy was collected for 67 cases used for this pilot study. Results: Full entrustability was observed in 5 of the 108 observed cases. Residents in our study did not report full autonomy. Spearman's rank correlation coefficient identified that resident entrustability was positively correlated with perceived resident autonomy (ρ = 0.66, p < 0.05). Ordinal logistic regression assessed the relationship between resident entrustability and autonomy. The relationship persisted while controlling for PGY level, gender, and case complexity (OR = 8.42, SEM = 4.54, p < 0.000). Conclusions: Resident entrustability is positively associated with perceived autonomy, yet full entrustability is not translating to the perception of full autonomy for residents.