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The current study explored trainee therapists’ experiences in alliance-focused training (AFT), a form of group supervision focused on training therapists to recognize and negotiate alliance ruptures. We analyzed interviews with 36 former trainees who received AFT during their predoctoral psychology internships. Findings centered on trainees’ views of the central AFT tasks of videotape analysis, awareness-oriented role-plays, and mindfulness training; the supervisor's stance, including the provision of support and validation and the extent to which the supervisor served as a positive role model; and the impact of AFT on trainees’ clinical skills. Many trainees reported that AFT increased their awareness, acceptance, and comfort with navigating ruptures, but some trainees reported that AFT supervisory tasks were anxiety-provoking and that AFT made them less comfortable in session. The findings underscore the challenges that AFT presents for trainees, who are asked to take risks in supervision, and for supervisors, who need to create a safe space for trainees and model sensitivity to supervisory ruptures. The findings also point to the potential benefits for trainees who feel safe and supported enough to explore the most challenging therapeutic moments in the context of a group supervision.