Children of incarcerated parents are an understudied and underserved population, though recent intervention efforts have begun to address the needs of this group. The current study investigated a mentoring program targeting children with incarcerated parents. Using multiple methods and informants, the study explored the frequency and length of meetings between matches, relationship quality, rates of match termination, and reasons for termination in 57 mentor-child dyads during the first six months of involvement in the program. Quantitative analyses revealed that more than one-third of matches terminated during the first six months of participation. However, for those matches that continued to meet, children who saw their mentors more frequently exhibited fewer internalizing and externalizing symptoms even after controlling for initial behavior. In monthly interviews with participants, themes emerged about the challenges associated with the mentoring relationship and reasons for match termination. Implications for researchers, practitioners, and policy makers are discussed.