Experiences with racism and other emotionally laden encounters are intricately entangled with parents' motivations to take direct action that can lead to voluntary separation from school or homeschooling. Using the Hoover-Dempsey and Sandler (HDS) model, this article expands parental involvement by including homeschooling and examines the usefulness of including emotion as a discernible motivator of parental involvement. Research on Black homeschooling is used as an example to explore the psychological and socio-emotional dilemmas parents face when preparing their children to become self-sufficient in an anti-Black lived context. Particular focus is given to parental role construction and efficacy beliefs to describe the intersection of emotions leading to parental actions toward involvement. Marchand et al.'s process of critical action is detailed to further illustrate the complexities of Black parents who actively engage in activities to combat discrimination. New insights on theory adaptation and pathways to inform practice, and recommendations for future research on parental involvement and Black homeschooling are also provided.