Homeless youth are a difficult to reach subgroup of homeless individuals who require a unique level of intervention given their specific vulnerabilities as young people. They experience higher levels of trauma than their housed counterparts and lack parental guidance around concrete life skills as well as emotional support. This article provides a description of the adaptation process of a pilot life skills empowerment program designed to help homeless youth integrate successfully into the community by providing life skills training, emotional support, and social justice awareness. Youth participated in twice weekly group sessions and one-to-one mentoring with community volunteers. The adapted program was piloted in 3 cycles with small groups totaling 20 youth over the course of 18 months. Mixed methods were used to evaluate youths’ experiences in the program. While the sample size was too small to detect statistical significance, scores on validated measures (Antonovsky’s Sense of Coherence measurement tool and the Post-Traumatic Check-list Civilian version) demonstrated improvements in coping and sense of coherence and decreases in trauma symptoms. Qualitative findings supported the quantitative trends, demonstrating that youth felt more confident and hopeful about their futures, were able to set goals for themselves, and begin training programs and jobs. Youth were also able to develop trusting and meaningful relationships with mentors, staff, and peers. Implications for future program development and practice, future research, and social services education are discussed.