Considerable research has examined the personal factors and practices associated with transition-age youth with disabilities achieving higher employment rates and greater self-sufficiency as adults, but there is limited evidence on the longer-term effectiveness of these practices and services. This study examines the role of youth's use of transition services and work experiences in the pathways that youth with disabilities followed to longer-term employment and education outcomes drawing on data from a federal initiative known as Promoting Readiness of Minors in Supplemental Security Income (PROMISE). PROMISE aimed to improve the long-term self-sufficiency of youth receiving Supplemental Security Income by funding six programs to provide educational, vocational, and other services to youth and their families as well as improve service coordination between state and local agencies.