Youth with disabilities have consistently poor postschool engagement outcomes in employment and postsecondary education and training. At least once every 6 years, states are required to submit a State Performance Plan in which they report performance on the progress of students with disabilities (20 U.S.C. 1416(b)(1)). Indicator 14 requires states to collect postschool outcome data 1 year after students exit high school. The purpose of this exploratory study was to examine the impact of student-, school-, district-level, and combined (student + school + district) factors on engagement outcomes for youth with high incidence disabilities across 3 years. Findings from logistic regression analyses indicate that student-level, district-level, and combined factors were significant in predicting postschool outcomes of employment and postsecondary education.