It is estimated that about 7.3 million (or about 15%) public school students are currently enrolled in Special Education in the United States, and their enrollment has increased steadily over the past decade (U.S. Department of Education 2023). Students in Special Education can be labeled as 'different' and/or 'disabled'. These labels may be internalized by students, leading to lower self-esteem and experiencing symptoms of depression. My dissertation aims to uncover the possible link between enrollment in Special Education and mental health in adolescence into emerging adulthood, and the differences for Black students and white students. I take into consideration school contextual variables (school satisfaction, student prejudice, teacher unfairness, and expulsion), which may impact the mental health of students and help to further explain the experiences of labeling that students may encounter in the school environment. Additionally, I include resiliency factors (social support and educational expectations), which may help to alleviate the stress that students experience from being labeled a 'Sped kid' in school. Using national longitudinal data, my regression results suggest that enrollment in Special Education or having a learning disability is associated with lower self-esteem and higher levels of depressive symptoms in adolescence. My subsample analyses discover differences in school context and resilience between Blacks and whites and between those enrolled in Special Education and not. These findings expand our knowledge of racial disparities and the social determinants of mental health. Depression is one of the most frequently occurring mental health problems among adolescents, therefore it is urgent to alleviate the distress experienced by students and to explore the implications of stigmatizing labels, which harm mental health. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]