Teenage pregnancy is linked to poverty, poor child physical and psychological well-being, child maltreatment, family dysfunction, and reduced educational attainment. Furthermore, less than half of teenage mothers birthing a child prior to age 18 earn a high school diploma. Consequently, alternative academic programs have been developed to combat these maladaptive outcomes; however, the effects of such outcomes, particularly from perspectives of program graduates, are not well understood. Therefore, the purpose of the current study was to explore outcomes of an alternative school program from the perspectives of pregnant and parenting teenage students who have graduated from such a program. Graduates of an alternative high school program (N = 8; Mage = 20.75 years, SD = 1.67) were interviewed and data were qualitatively analyzed for themes. Emergent themes included improved parenting skills, academic and career development, life skills acquisition, and personal and positive relationship development. Educational and developmental benefits for participants’ children, program challenges, and opportunities for improvement were also described. Overall, results demonstrate that improving child well-being can be accomplished by promoting a holistic perspective to the physical, emotional, and mental health of teenage mothers while also providing educational opportunities. The application and generalization of program outcomes for others in related fields are discussed.