Women who have children during high school are at-risk for poor educational and economic outcomes. Literature lacks information regarding college readiness among pregnant and mothering teens (PMTs) who graduated from alternative education (AE) programs. Teen mothers who receive college preparation in high school may go on to earn degrees, improving their chances at more stable and secure financial futures. A basic qualitative approach and purposive sampling was used to locate 10 former PMTs who graduated from AE programs and college and shared their stories via one-on-one semistructured in-depth interviews regarding their experiences in AE programs and how they prepared them for college. Schlossberg's transition theory (TT) was used as the conceptual framework and provided the structural lens to interpret participants' life transitions into motherhood, AE programs, and eventually college. Participants' experiences involving AE programs and academic practices for college success were explored. Transcribed data underwent qualitative content analysis through a directed approach and via manual coding and thematic analysis, produced five emergent themes that aligned with the TT: parenting and childcare accommodations, academic practices for high school without college prep, increased levels of support in college, personal traits and habits, and self-navigation to locate college academic assistance and finances. Administrators and teachers in AE programs may benefit from results of this study by maximizing PMTs' potential for college success. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]