Discussions of the School-to-Prison Pipeline often focus on a unidirectional pathwaybetween the education and justice systems, but prior research suggests that it is important to also assess the reverse relationship: how justice system involvement impacts one’s education. I expand on this prior work by exploring how justice system involvement in adolescence impacts key educational outcomes and testing some of the potential nuances of this relationship. The current study examines the relationship between justice system involvement in high school and educational outcomes for the 2013 Maryland public school ninth grade cohort. I utilize propensity score matching to compare justice-involved and similarly situated non-justice-involved youth in their likelihood of suspension in the 12th grade, graduation, and postsecondary enrollment. I compare these impacts across school district and the level of one’s system involvement, which includes arrest, adjudication, in-community placement, and out-of-community placement (i.e., incarceration). I also explore the potential role of absence from school in the relationship between justice system involvement and educational outcomes and how the impact of system involvement may vary between youth of different racial identities and sexes, including at the intersection of one's race and sex. I conduct sensitivity analyses that further assess the nuances of this relationship based on the timing and dosage of one’s system involvement and different specifications of my educational outcomes. I find that justice system involvement is associated with worse educational outcomes and that the impact of involvement varies by school district, one’s level of system involvement, and their demographic characteristics. I also find that school absence may impact this relationship. Overall, this study builds upon prior research of the consequences of justice system involvement, particularly on one’s education, by exploring the nuances of this relationship based on one’s demographic characteristics, educational context, and factors related to their system involvement. The results of this study suggest that perhaps the School-to-Prison Pipeline may be best conceptualized as a School-to-Prison Cycle that could impact adolescents long after their system involvement.