Research has demonstrated the effectiveness of family-based programs for reducing adolescent risk behaviors and promoting adolescent health; however, parent engagement, specifically in terms of recruitment and retention, remains a consistent challenge. Recruitment rates for family-based prevention programs range from 3 to 35%, while, on average, 28% of caregivers drop out before program completion. Thus, engagement of parents in prevention programming is of utmost concern to ensure families and youth benefit from implementation of family-based programs. In this manuscript, two Centers for Disease Control and Prevention-funded projects share their experiences with engagement of parents in violence prevention programs. Problems related to parent engagement are reviewed, as are structural, attitudinal, and interpersonal barriers specific to recruitment and retention. Examples of successful implementation strategies identified across urban and rural sites are also analyzed and lessons learned are provided.