Substance use disorders among adolescents can have detrimental and long-term impacts on their educational goals. As such, high school students in recovery who wish to pursue a college education can face unique challenges, ranging from a potential history with the criminal justice system and inequitable evaluative metrics poorly influencing the admission process to the prevalence of parties on campus posing a risk to sobriety. To that end, the overarching goal of this work was to understand how a higher education institution could change or tailor existing programming to support students in their recovery, address perceived barriers, and potentially reduce stigma, making the college campus a more supportive environment. For this research, we collected qualitative data via small group interviews with students at three Massachusetts-based recovery high schools to understand their perceived barriers and facilitators to postsecondary education. A deductive qualitative content analytic technique was used to review and analyze the data, and four main themes emerged: (1) financial concerns, (2) stigma related to addiction, (3) the fragility of sobriety, and (4) the importance of social support. The results of this analysis are framed in the context of the Recovery Capital Model (RCAM), an adolescent-adapted ecological model consisting of four domains of resources that allow for an individual to succeed in recovery: financial, social, human, and community recovery capital. Considerations and recommendations for higher education institutions to welcome more students in recovery into their schools are discussed.