A litany of literature on teenage pregnancy and subsequent motherhood highlighting causes for teen pregnancies and subsequent effects on the teens academic performance and development exist, but there is a dearth of literature that reveals the challenges many teenage mothers face when they are re-admitted back to school after giving birth. Lack of nuanced understanding of how the teens undertake their triple roles as mothers, parents and student is prevalent. The article highlights the plight of teenage mothers who are readmitted back to school in Zanzibar. Primary data were obtained using public rapid appraisal methods. Selected respondents included school heads, teachers and teenage mothers from the selected secondary schools as well as officials from the Ministry of Education and Vocational Training of Zanzibar. Secondary information was sourced from grey literature. It was established that most teenage girls in secondary schools are more likely to become pregnant at the ages between fifteen to seventeen years when they are in secondary education level. On average, most teenage mothers returned to school in less than three months after delivery especially those who are married and had adequate support for taking care of their newborns. Those with inadequate support to care for their babies and not in conjugal relationship, take long to return back to school and in extreme cases, they fail to resume studies. All teenage mothers, regardless of their age and marital status, experience individual and institutional challenges upon returning to school. Unmarried teenage mothers suffer more compared to those who are married. In coping with individual challenges, most teenage mothers seek help from diverse sources. Mainstreaming gender in the policy frameworks that govern girl education in Zanzibar is found wanting, specifically, the Government of Zanzibar should introduce a clear implementation strategy, having the requisite law notwithstanding, to ensure that all pregnant teenage girls are supported and encouraged to return to school after delivery and further institute an effective monitoring and evaluation system to ensure that educational and other rights of teenage mothers are met.