This study explores the impact of mandatory work requirements on welfare-reliant mothers struggling to pursue post-secondary education, and the overwhelming difficulties created by rigid and punitive policies at both the federal and state levels. By placing the stories of student mothers at the center of this policy and practice study, the authors hope to illuminate the intersecting obstacles that threaten the ability of student mothers to complete post-secondary education and to insure their families’ survival. They document and analyze the policies and practices of the Family Independence Agency and Work First agencies: the enforcement of escalating mandatory work requirements and the administration of welfare, education, and child care policies. The stories also highlight the resourcefulness and determination of student mothers as they struggle to learn while faced with mandatory work requirements, abusive agency practices, and parenting responsibilities.