With the expansion of online instruction in K-12 education, how and what is taught in a single course has the potential to affect the learning of thousands of students. Our mixed method study applies a critical lens to examine the extent to which four widely used online high school courses are culturally relevant and responsive. We used this instructional setting to examine the policies and practices of curriculum vendors in online courses targeting educationally disenfranchised youth that both runs parallel to and feeds into carceral systems. Online lessons reflected a culture of power, emphasizing normative cultural narratives, retreating to symbolic use versus application, and presenting neoliberal ideologies as fact. We end with a discussion of how systems can be leveraged to improve the educational experiences provided to students enrolled online. Substantial revision of existing online credit recovery programs is necessary to disrupt existing systemic inequities present in educational institutions and their contribution to the School-to-Prison Pipeline.