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Triennial data collected by districts and reported by states identify students with emotional and behavioral disorders (EBD) as the subset of students with disabilities (SWD) most negatively affected by the transition from high school to postsecondary school or employment. Unfortunately, the quantitative data collected by the state does not provide sufficient information to understand the experiences of youth with EBD or for districts to improve transition outcomes. Specifically, the data reported does not inform the instructional content at the district level. In this mixed methods study, I analyzed disaggregated state-level data and explored the perceptions of youth with EBD in relation to their transition-specific instruction and outcomes to answer the following research questions: (1) How do the post-school outcomes for all SWD at West High compare to the post-school outcomes available for New Jersey?; (2) How do the post-school outcomes for students with EBD at West High compare to the post-school outcomes for the larger NJ population of students with EBD?; (3) What was the experience of students with EBD in the Disability Awareness and Transition (DAT) program post- graduation?; and (4) What do DAT students describe as influencing factors in their postsecondary outcomes? I interviewed eight high school graduates to explore their lived experiences postsecondary. More specifically, I explored how their time in one district’s disability awareness and transition program informed these experiences. Six themes emerged explaining their experiences and four in relation to their recommendations. The experiences of the participants were like a Roller Coaster Ride (Theme 1) beginning with the Disconnect (Theme 2) between understanding the need for applying what was taught in high school in postsecondary environments. Students described the impact of new Social Experiences (Theme 3) and the transition from supported decision making to intended independent decision making (Theme 4), emerging self-awareness (Theme 5), and self-determination (Theme 6) with many ups and downs. Themes emerged indicating that participants experienced support in small (Theme 7) community college/home environments and that they relied on support systems (Theme 8) and disabilities services to calm their ride (Theme 9). It is within all of these experiences that the participants identified age and lived experiences (Theme 10) as one of the most important influencing factors. Results inform disability awareness and transition instruction, recommendations for program improvement, and means of improving outcomes.