The present study examined young children’s attachment behaviors during paternal incarceration and reported on initial validity of a new measure used to rate children’s attachment-related behaviors and emotions during visits in a corrections setting. Seventy-seven children, age 2 to 6 years, and their jailed fathers and current caregivers participated in the home visit portion of the study, whereas 28 of these children participated in the jail visit. The results indicated that 27% of children witnessed the father’s crime and 22% of children witnessed the father’s arrest, with most children who witnessed these events exhibiting extreme distress; children who witnessed these events were more likely to have insecure attachments to their caregivers. Consistent with attachment theory and research, caregivers who exhibited more sensitivity and responsivity during interactions with children and those who provided more stimulating, responsive, learning-oriented home environments had children who were more likely to have secure attachments (measured with the Attachment Q-Sort). We also found preliminary evidence for the validity of our new measure, the Jail Prison Observation Checklist, in that children’s attachment-related behaviors and emotions during the jail visit correlated with their attachment security observed in the home. Our observations indicate that, in certain contexts, noncontact visits with incarcerated parents can be stressful for children and that children’s caregivers may play a significant role during these visits.