To understand how youth desist from crime after their first arrest, it is necessary to investigate their primary support system: their parents. As such, this study examined the reciprocal effects of justice system contact on the mother-child dyad. Interviews with 317 mothers and their sons from Orange County, CA, Jefferson Parish, LA, and Philadelphia, PA were conducted semiannually over two and a half years. At the beginning of the study, the sons were first-time offenders aged 13-17 and mostly non-White (i.e., 19.2 White, 56.5 Latino, 21.5 Black, and 2.8% another race/ethnicity). The results revealed that a high quality initial mother-son relationship reduces youths' re-offending over time. Furthermore, as mothers perceived that their sons were offending more, they reported less warmth in their relationships with their sons two and a half years later. Interestingly, youth's age emerged as a moderator. First, older youth were less likely to engage in reoffending if they had a warm maternal relationship. Second, decreases in relationship warmth associated with re-offending were steeper for younger youth. The findings have implications for juvenile justice policy in terms of improving probationary outcomes for youth offenders, and alleviating the financial and emotional burden on justice system-involved families.