Purpose <p>Operative entrustment decisions are shaped by individual and contextual factors. Despite the growth of robotic surgery, resident autonomy often remains limited. This study explored how faculty surgeons approach entrustment decisions in robotic surgery and examined the perceived impact of a resident robotic portfolio.</p> Methods <p>We conducted a qualitative study with semi-structured interviews of robotic surgical faculty at two academic centers who operate with general surgery residents. Purposive sampling identified faculty with varied specialties and years of experience. A sample resident portfolio was developed including objective details about resident robotic experiences. Interviews were transcribed verbatim and analyzed using inductive thematic analysis.</p> Results <p>Participants included 13 faculty surgeons whose most common robotic case types were hernia (<i>n</i> = 8), colorectal (<i>n</i> = 3), and bariatrics (<i>n</i> = 2). Primary themes identified were entrustment “pre-test probability,” validation of initial entrustment, and ways in which the robotic platform both promotes and challenges trainee entrustment. The resident portfolio was informative and increased the faculty’s “pre-test probability” of prospective entrustment. Despite objective data of the portfolio, faculty still need to validate the trainee’s robotic skill level through direct observation. Faculty promote entrustment by utilizing dual consoles and telestration, but residents must adapt to the robotic console and learn tactile visual cues.</p> Conclusion <p>Our findings highlight factors that influence a “pre-test probability” of prospective entrustment in robotic surgery. While the resident portfolio is a tool that could promote competency-based entrustment, faculty need to validate the robotic skillset and utilize teaching strategies tailored to the robotic platform.</p>