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This qualitative case study explores the experiences of participants in “Empowering Parents,” a successful parent leadership program in a large Mid-western urban school district. As emerging parent leaders immersed in family outreach work, the participants in this study have a unique perspective on family engagement practices in urban education. The study focused on the programs parents created for their own schools and participant insights regarding how urban educators might improve their own family engagement work. The findings suggest that educators could enhance their engagement efforts by demonstrating a passion for their work as teachers, communicating a concrete classroom vision, and reimagining opportunities for family participation. Implications for both school leaders and teacher educators based on these findings are discussed.