Youth with disabilities face significant barriers to achieving education and employment outcomes. While substantial research has examined the educational and employment outcomes of youth with disabilities, there has been less research on the context within which these outcomes occur. This study builds on a five-year evaluation of the impact of the Promoting Readiness of Minors in Supplemental Security Income (PROMISE), a federal initiative that aimed to improve the long-term self-sufficiency of youth ages 14-16 receiving Supplemental Security Income, which is a means-tested benefit intended for people with very low incomes. We provide a more detailed picture of PROMISE youth's employment, education, training, and living arrangements and benchmark youth outcomes against those of similarly aged youth with and without disabilities.