Approximately 30% of teenagers in South Africa report ‘ever having been pregnant’, the majority, unplanned. While this number has decreased over the past few decades, it is still unacceptably high. The figure is for all teenagers. (13-19 years old), but motherhood for an 18 or 19 year old has very different implications than for a young teenager, one aged 15, for example. Therefore this report tries, where possible, to be mindful of differing experiences of pregnancy and motherhood across the teen years. A major concern of this report is to examine ways in which all pregnant teenagers and teenage mothers be supported to remain in school and, for those that do remain in, and return to school how can they be supported in their dual role and responsibilities as both learner and mother? The literature, and the interviews the author undertook, highlighted that the most important factor for determining whether a teenage mother would return to school was whether she had family support (in particular from her mother) to assist her with child-care responsibilities, and/or money to pay for childcare. Supporting a teenage mother with daily childcare responsibilities seems to be the most critical factor that will enable her to return to school.