Despite efforts made by the Kenyan government to rehabilitate and train former street youth, their numbers have risen alarmingly. Reports in the media focus on those who joined the national youth service (NYS) in 2003 but no known study has followed them out to ascertain the effectiveness and appropriateness of the program which was meant to help their transition to work, since they graduated in 2005. This study investigated rehabilitation and vocational education with regard to transition to work and job retention of trained former street youth. Participants included two employers, one administrator, one coordinator of skills training, and 46 of the former street youth. The findings indicated that courses offered at the NYS were relevant to the labor market hence, aided the youth in securing jobs. It was found that beyond technical skills, one needs personal skills to maintain the secured employment. The study recommended that recruitment be pegged on institutional training facilities, capacity, and that the content of training be continually reviewed to tailor it to market needs. Institutions also need to explore linkages with various employment agencies.