"Mentoring" has been defined as "a sustained relationship between a young person and an unrelated adult in which the adult, along with the child's parent, provides counsel, friendship, ongoing guidance, instruction, and encouragement aimed at building up the young person's strengths and developing or increasing his/her competence and confidence." Most experts who have examined mentoring programs for inmates' children have concluded that, when implemented appropriately, they improve children's social-emotional skills; increase their capacity for attachments; and produce stronger, healthier relationships between children and significant others. This improvement in these relationships leads to documented outcomes in social and academic competence. This article cautions, however, that the premature termination of mentoring matches, matches that are not built on mutual respect and the development of trust, and matches that alienate the child's family can possibly do harm. The author advises that longevity of the match is critical to success; mentors must honor the significance of the prisoner for the child; loyalty conflicts for the child and alienation for the caregivers must be minimized through policies and practice; and training and ongoing supervision that supports the mentor and the match are essential. 6 references