In higher education, the responsibility for submitting course assignments falls on the student. However, it can be difficult for adult learners—particularly students facing structural inequalities and disparities—to meet assignment deadlines. The conventional approach of removing points or not accepting late assignments assumes that students are disrespectful, irresponsible, or lazy rather than overwhelmed or struggling. From a Black collectivist viewpoint, such an approach may be considered a dismissive, socially isolating, stigmatizing injustice. The missed assignment becomes a “debt with interest” that the student cannot repay. Black college students, whose worldview emphasizes community and collective responsibility, witness the disjuncture between their treatment in the academy versus personal finance options that allow them to restore, for example, a delinquent credit account. The purpose of this chapter is to provide higher education instructors with philosophical and practical guidance, within a restorative justice framework, to co-create structured catch-up plans with students.