Teen mothers and their children are often seen as being involved in a cycle of low literacy. However, as people whose lives have paralleled societal changes in literacy and digital technology, there is a possibility that the literacy experiences of today’s teen mothers and their children differ from those of the past. This study explores the role of digital technology in the literacy lives of teen mothers and their children. Eight teen mothers were interviewed about their recollections of their early childhoods as well as their contemporary experiences with digital technology in their own lives and in the lives of their children. The early experiences of teen mothers were both educational and entertainment oriented, whereas their later experiences are quite varied. However, the experiences that their children have with digital technology and literacy reflect a prioritization of educational uses as well as a managed approach to their children’s engagements that also emphasizes the children’s interests and development.