Study findings showed that released prisoners relied very heavily on their families for support in navigating virtually every aspect of the reentry experience, from assistance with housing and employment to financial support and overall encouragement. Prisoners’ expectations for family support were consistently met or exceeded for most study participants. In addition, the quality of family relationships improved after release, as did prisoners’ views on the importance of family in staying out of prison. An important implication for practice is the fact that families provide even more support than soon-to-be-released prisoners anticipate suggesting that they shoulder a significant burden of the reentry challenges released prisoners face. Families may benefit from social support and services, as well as the development of programs that capitalize on the family support. While there have been very few attempts to understand the role of family relationships and support on reentry success or failure, it is reasonable to hypothesize that family members have an impact on released prisoners as they meet the challenges associated with their return to society. This article explores the question of whether prisoners’ expectations of how life will be on the outside are realized with regard to family support, as well as to the extent to which those expectations are met. The article examines the differences between anticipated and actual levels of familial support among a sample of 413 male prisoners returning to the cities of Baltimore and Chicago. Figures, notes, and references