Representations of attachment relationships were assessed in 54 children ages 2.5 to 7.5 years whose mothers were currently incarcerated. Consistent with their high-risk status, most (63%) children were classified as having insecure relationships with mothers and caregivers. Secure relationships were more likely when children lived in a stable caregiving situation, when children reacted to separation from the mother with sadness rather than anger, and when children were older. Common reactions to initial separation included sadness, worry, confusion, anger, loneliness, sleep problems, and developmental regressions. Results highlight need for support in families affected by maternal imprisonment, especially efforts to promote stable, continuous placements for children, in addition to underscoring the importance of longitudinal research with this growing but understudied group.