Generational cycles of teenage pregnancy trend among many families create economic, social, and health problems on teen parents and their families. Scholarly literature includes quantitative studies addressing the issue of teenage pregnancy but there is not many qualitative studies about the family cycle of teenage pregnancy among a highly-concentrated area of African American females in the Southern region of the United States. The life history theory and the socialization and social control theories of the intergenerational transmission of early childbearing served as the theoretical framework.. A qualitative case study is designed to identify factors that contributed to generational cycles of teenage pregnancy among families in the Southern region of the United States. Data were collected using questionnaires from 3 family triads of teenage mothers. Data were analyzed and display tables were created. The results indicated that participants had a lack of knowledge of proper contraceptive use and experienced peer pressure to engage in sexual behaviors. Teenagers looked at their mothers and sister's pregnancy in a favorable way making their pregnancy acceptable within families. Most participants felt teenagers should wait before becoming pregnant. Participants felt teenage mothers could overcome obstacles associated with teenage pregnancies. Pregnancy prevention programs may benefit from the results of this study through parenting programs to teach mothers, who were pregnant in their teen age, how to communicate with their teenage daughters about their sexual experiences.