This study examines the impact of a “natural experiment” that gave students the choice to place into or out of developmental math because of an unintended mistake made by a community college. During self-placement, more students chose to enroll in gateway college- and transfer-level math courses, however, greater proportions of female, Black, and Hispanic students enrolled in the lowest levels of math relative to test-placed counterparts. Difference-in-difference estimates show that self-placement led to positive outcomes, but mostly for White, Asian, and male students. This evidence suggests areas of concern and potential for improvement for self-placement policies. Self-determination theory, behavioral decision theory, and stereotype vulnerability provide possible explanations for the observed changes.