Poor health, social exclusion, and stigma are usually associated with adolescent pregnancy and parenting, resulting in girls' suspension and, in some instances, expulsion from school. While most African states, including Lesotho, have laws and policies protecting the rights of all children, including adolescents, to enroll and be retained in school, implementation is lagging behind. Using a socio-legal approach, the article explores the challenges in implementing policies and guidelines on school re-entry following pregnancy and/or parenthood, with particular reference to Lesotho. It argues that, despite the adoption of enabling laws and policies protecting sexual and reproductive health rights, and the right to education of pregnant and parenting adolescent girls, punitive and discriminatory practices continue to serve as barriers that undermine countries' human rights commitments. The barriers are attributable to the influences of family, societal, religious and cultural beliefs and practices. To address these barriers, this article proposes comprehensive, innovative, gender-transformative, targeted and rights-based interventions, and supportive policies and strategies, to facilitate continuous awareness-raising, social and attitudinal change, and social justice.