As a response to the national dropout/pushout crisis, alternative high schools were first developed to meet the needs of students that were typically unavailable in traditional high schools (Kelly, 1993). Since the beginning of their establishment, alternative schools gained the reputation of serving as “dumping grounds,” and softer “juvenile detention centers,” for youth labeled “troubled” and “problematic” (Kim, 2011). Scholars have also argued that alternative schools are often “second chance” opportunities that work as “idealistic heavens” for students deemed unsuccessful in a traditional school system (Inbar, 1995; Kim, 2011). Nationwide, traditional high schools are recognized as some of the top feeder schools in the alternative education system, yet there is limited critical research to understand the role of institutional and systemic racism in the overrepresentation (Malagon & Alvarez, 2010) of Black and Latinx students in alternative schools. To hold institutions more accountable for the equitable education of Students of Color, this dissertation calls attention to the policies and practices governing schools that force large numbers of Black and Latinx students into enrolling in alternative schools. Guided by Critical Race Theory (CRT), this study provides a deep dive into the process of school transfer in one California school district to reveal structural flaws and inconsistencies that are often racialized and are supported by deficit framed ideologies that result in internalized racism, anti-black racism, and linguistic racism. Using qualitative methods, this study also draws on counterstorytelling methods to include counter-narratives of student resistance to demonstrate how they rely on their resistant capital (Yosso, 2004) to navigate their transition into continuation high school and defy normalized expectations.