School dropout among pregnant secondary school girls remains a significant educational and social concern in Zimbabwe despite policies supporting their continued participation in education. This study sought to develop contextually appropriate strategies for reducing school dropout among pregnant secondary school girls in Mbare, Harare. A qualitative research approach was adopted to explore participants’ experiences and perspectives. Thirty-seven participants were purposively selected, comprising 25 pregnant girls and young women aged 14–22 years, 6 teachers, and 6 social workers. Data were collected through semi-structured in-depth interviews with the girls and key informant interviews with teachers and social workers. The data were analysed thematically. The findings revealed that pregnancy-related stigma, discrimination, inadequate family support, financial hardship, caregiving responsibilities and inflexible school environments contributed to absenteeism and eventual withdrawal from school. Participants also reported limited psychosocial support, weak coordination among schools, families and social-service providers, and inconsistent implementation of policies protecting pregnant learners’ right to education. The study proposes an integrated strategy comprising school-based psychosocial support, family engagement, flexible learning arrangements, financial and material assistance, childcare support, anti-stigma programmes and coordinated case management involving teachers and social workers. It concludes that reducing dropout requires more than allowing pregnant learners to remain enrolled; it demands a supportive and responsive system that addresses their educational, psychosocial, economic and caregiving needs. The proposed strategies may guide schools, social workers and policymakers in strengthening educational continuity among pregnant learners in Zimbabwe.