Current data suggest that homeschooling is a diverse and growing social movement. Unfortunately, the homeschooling narrative reflected in research is often skewed by the socioeconomic status, political power, and cultural interests of White, two-parent, middle-class, homeschooling households, marginalizing the experiences of a growing population of Black homeschoolers. Considering that the plausibility of homeschooling is dependent upon access to social, economic, and temporal resources, this study examines the resources that Black families identified as substantive to sustain their homeschooling efforts. Relying on 20 in-depth interviews, I utilized the theoretical frames of symbolic interactionism, cognitive sociology, and intersectionality and the coding procedures of grounded theory methods to analyze the narratives of Black homeschooling parents. Ultimately, I found the metaphor of coloring outside the lines to be a fitting representation for Black families resourcefulness in homeschooling. In addition, I introduce complicit privilege and rearticulated license—the mechanisms through which Black families navigated stratifications.