Pregnant female offenders face multiple adversities that make successful parenting difficult. As a result, their children are at risk of developing insecure attachment and attachment disorganization, both of which are associated with an increased likelihood of poor developmental outcomes. We evaluated the outcomes of participants in Tamar's Children, a 15-month jail-diversion intervention for pregnant, nonviolent offenders with a history of substance abuse. All women received extensive wrap-around social services as well as the Circle of Security Perinatal Protocol (Cooper, Hoffman, & Powell, 2003). We present data on 20 women and their infants who completed the full dosage of treatment (a residential-living phase from pregnancy until infant age six months and community-living phase until 12 months). Results indicated that (1) program infants had rates of attachment security and attachment disorganization comparable to rates typically found in low-risk samples (and more favorable than those typically found in high-risk samples); (2) program mothers had levels of maternal sensitivity comparable to mothers in an existing community comparison group; and (3) improvement over time emerged for maternal depressive symptomatology, but not other aspects of maternal functioning. Given the lack of a randomized control group, results are discussed in terms of the exploratory, program-development nature of the study.