This article reports findings from an ongoing study that examines the experiences and engagement of pregnant and parenting youth (PPY) attending an alternative school in Chicago and the sorts of instructional approaches and activities that can promote their social justice-oriented advocacy and leadership skills. This project used Youth Participatory Action Research (YPAR) and ethnographic methods involving a team of African American and Latinx PPY in designing and implementing research projects and media campaigns aimed at better understanding the experiences of young parents. This study found that PPY gained valuable knowledge and skills from their participation in engagement and advocacy projects in which they had opportunities to address issues relevant to their lives and communities. This study hopes to inform the development and implementation of services and initiatives for PPY and to help reimagine possibilities for PPY's role in advocacy and activism on behalf of themselves and their children.