Pregnant women and mothers were among the thousands of individuals who were sentenced to at least three years’ penal servitude and admitted to the nineteenth-century Irish female convict prison. While some babies were born behind bars, others were permitted to accompany their convicted mothers into the prison after the penal practice of transportation had ceased. Other dependent children were separated from their convicted mothers for years, cared for by family members or friends, or accommodated in Ireland’s growing web of institutions. Using individual case studies, this article focuses on convict mothers and their young offspring. It draws attention to the increasing restrictions on the admission of infants that were imposed as the nineteenth century progressed, the problems that children of various ages in the penal system seemed to pose for officials, and the difficulties faced by incarcerated mothers who wished to maintain communication with their offspring. This article argues that while there were benefits to parenting within the confines of the prison, sentences of penal servitude had a significant impact on the lives of dependent offspring by dislocating families, separating siblings, or initiating institutional or other care that broke familial bonds permanently. In so doing, the article reveals attitudes towards motherhood as well as female criminality and institutionalization generally during this period and sheds light on an aspect of convict life unique to the women’s prison.