The aim of the current study is to explore experiences of trainees engaged in alliance-focused training (AFT), a group supervision modality with an explicit focus on awareness of ruptures and implementation of repair strategies. Using cognitive behavioral therapy (CBT) group supervision as a point of comparison, the study examines supervisory alliance, ruptures, group cohesion and safety, and supervision impact. Method: Eighty-three trainees (clinical psychology interns, advanced-level psychology externs and psychiatry residents) at a metropolitan medical center in New York City who received supervision in CBT (N ϭ 38) or AFT (N ϭ 45) reported on their group supervision experience. Participants had a mean age of 29.5 (SD ϭ 4.9); 77% were women; 84% of participants identified as White, 7% as Multiethnic, 6% as Hispanic/Latinx, 1% as Black, and 1% as Asian. Participants reported on occurrence of ruptures with their supervisor, supervisory alliance (Working Alliance Inventory-Short), group safety, supervision depth and smoothness (Session Evaluation Questionnaire), and group cohesion (Group Climate Questionnaire). Mixed and general linear models, and correlation analyses were used for analysis. Results: All trainees reported equally low incidence of ruptures with their supervisor alongside high ratings of supervisory alliance. Trainees in AFT reported experiencing less safety, smoothness, and greater intergroup conflict than trainees in CBT supervision; however, they also reported stronger group engagement and a deeper supervision experience. Conclusions: Results suggest that AFT may provide a rich environment to foster a certain level of discomfort and risk-taking that may facilitate an engaging and meaningful learning experience.