While recent research has shown the long-term effects of teen pregnancy are not as devastating as once predicted, more than 40 years after the passage of Title IX legislation mandating equal educational opportunities for pregnant and parenting teens, only 50% of teen parents graduate high school, lagging far behind their non-parenting peers. This qualitative case study examined six parenting teen mothers attending three different educational settings to discover what factors contributed to their educational resiliency and helped them graduate from high school. The portraiture method was used to create life stories and their voices resonate throughout the study to paint a portrait of the struggles and triumphs they faced as they navigated life as a high school mother. Five themes emerged of struggle, support, hope, and perseverance. An in-depth look at how these themes played into their educational resiliency is explored, as well as advice for educators and policy-makers alike.