This study explored the perceptions and experiences related to pregnancy and parenting support among youth while homeless. This study employed a qualitative descriptive design using data collected from focus group discussions. We assessed the experiences and perceptions of youth related to pregnancy and parenting support. Eighty-one youth participated in eight focus group discussions and were recruited from shelters, drop-in centers, and organizations that serve youth in a large metropolitan areas in the southern United States. Thematic content analyses were used to generate results from the qualitative data. Four main themes emerged: youth encountered barriers to accessing healthcare services at the individual and system levels; pregnancy and parenting are stressful, especially during homelessness; support can help overcome the stresses of parenting; and embracing responsibility or “stepping up” is a positive influence of pregnancy and parenting during homelessness. Youth experiencing homelessness (YEH) face significant challenges to accessing healthcare services and adjusting to the parental role. Interventions for pregnant and parenting youth should be co-designed with and tailored for youth and address the existing health inequities within the healthcare and social service systems.