Employment is identified as a key factor that supports emerging adult Black men in reentry with making a successful the transition to adulthood. Although anti-Black racism creates barriers to them securing and maintaining legitimate employment, strength-based, education-focused alternative schools that are structured to meet their intersectional needs and experiences can help to promote their transition to employment. Yet, little is known about how these schools promote resilience and career readiness among this population and the ways in which they perceive these strategies to support their transition to employment. As such, this single, exploratory qualitative case study, which included observations, interviews, and focus groups sought to better understand how, if at all, an alternative school promotes resilience and career readiness among emerging adult Black men in reentry. Work readiness training, internships, and job search and placement assistance emerged as meaningful career and technical services and support that the young men with making the transition into employment. While working and attending school simultaneously posed challenges to school engagement and completion, the findings highlight the important promotive and protective role strength-based alternative schools can play in promoting positive educational and employment-related experiences and outcomes among emerging adult Black men in reentry.