Tensions between enrollment growth, faculty shortages, and persistent inequity characterize the current landscape of postsecondary computing education. As individuals who pursue graduate studies in computing are likely future leaders in the tech industry and academic computing spaces, colleges and universities need to restructure mechanisms of support for graduate school pathways in the field. Structured across three articles, I interrogate how collegiate computing environments may contribute to disparities in the psychosocial development and mentoring relationships of undergraduates who aspire to earn a computing graduate degree. The first article uses quantitative longitudinal data to examine the direct and indirect predictors of students’ self-confidence for computing graduate school admission, focusing on the role of introductory computing courses as well as computing self-efficacy and identity among 349 computing graduate aspirants. The second study uses critical quantitative approaches with a more nuanced sample from the same longitudinal dataset to investigate how power within computing departments shapes the nature of mentorship that 442 graduate aspirants receive and how such mentoring relationships may inequitably contribute to students’ computing self-efficacy and computing identity. The third study qualitatively explores one particular type of mentorship that graduate aspirants may have, centering on how 10 current graduate students in informatics make meaning of serving as “stage-ahead” mentors to undergraduate students in computing and how mentors’ approaches may be reflective of and shaped by the social identities of mentors and mentees as well as the organizational context. Collectively, these three studies expand what is known about computing graduate pathways and mentoring relationships in computing in two primary ways. First, findings document some of the salient inequities that characterize the stages between graduate aspiration and matriculation. Second, findings explore how different mentors in computing departments may face varying affordances or constraints in providing equity-minded guidance based on their positional power within the institution. These studies may be of particular interest to academic leaders and policymakers in collegiate computing spaces, as institutional changes to the opportunity, value, and rewards associated with mentoring and psychosocial support will be crucial to disrupt the minoritization and disparities that perpetuate students’ educational trajectories in computing.