Despite extensive research into juvenile justice interventions, there is a limited focus on family engagement, including parent–child experiences in these various programs. Even less research explores how families, specifically youth and parents, are affected by diversion from the traditional juvenile justice system. The current study fills this gap by drawing from in-depth interviews with 19 parents and 19 youths participating in a juvenile pretrial diversion program in Southern California. This research highlights how a diversion program can influence how families understand the justice system and law-related behaviors. The themes discussed include how diversion programs shape parent–child bonds, how parents navigate negative indictments of youth and themselves for participating in diversion, and the influence of external challenges and social forces shaping youth and parent experiences. Findings support the theoretical contributions from social bond and labeling theory. Implications and future research will also be discussed.