There has been an increasing focus on services aimed at engaging transition-age youth and emerging adults who are at risk of developing, or have developed, behavioral health disorders. However, a need remains for further development of specialized services for this population. This study evaluates a transition-age youth at risk (TYAR) training model within a Master of Social Work (MSW) program in New England. This convergent parallel mixed-method study collected student and field instructor data throughout each of the program's three consecutive years (cohorts 1, 2, and 3). Students' confidence related to working with TYAR clients increased over time within each cohort and throughout the program's development. Opportunities and challenges for collaborative and iterative evaluations of MSW curriculums are discussed.