PurposeSupervision training supports health care supervisors to perform their essential functions. Realist evaluations are increasingly popular for evaluating complex educational interventions, but no such evaluations exist appraising supervision workshops. Building on an earlier realist synthesis of supervision training, the authors evaluated whether supervision workshops work, for whom and under what circumstances, and why.MethodThe authors conducted a 2-stage realist evaluation during 2018–2019 to refine and develop program theory. The intervention involved half-day, face-to-face supervision workshops as part of an Australian state-wide government-funded program for health care and human services supervisors. Data collection involved realist interviews with 10 workshop developers (stage 1) and 43 supervisors (stage 2). The authors employed team-based data analysis using realist logic to refine and develop program theory by identifying contexts, mechanisms, outcomes, and context-mechanism-outcome configurations.ResultsDespite their brevity, the supervision workshops had many reported benefits for supervisors (e.g., improved satisfaction) through various perceived mechanisms pertaining to pedagogy (e.g., mixed pedagogies), workshops (e.g., optimal duration), and individuals (e.g., supervisor engagement). However, they also yielded negative reported outcomes (e.g., suboptimal knowledge gains) brought about by assorted perceived mechanisms related to pedagogy (e.g., suboptimal peer learning), workshops (e.g., content irrelevance), and individuals (e.g., suboptimal facilitator competence). Such mechanisms were thought to be triggered by diverse contexts including supervisors’ levels of experience, sector, and workplace supervision cultures.ConclusionsWhile the findings partly support the realist synthesis of supervision training and previous realist evaluations of faculty development, this realist evaluation extends this literature considerably. Health care educators should employ mixed pedagogies (e.g., didactic teaching, peer learning), relevant content, optimal workshop duration, and competent/engaging facilitators. Educators also need to tailor workshops according to supervisors’ contexts including the sectors and supervision cultures in which supervision is practiced, and supervisors’ levels of experience (e.g., experienced supervisors appreciated workshop brevity).