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This article examines the application of penal law in prisons based on the experience of inmates’ families, a perspective rarely explored in penal research. Indeed, beyond the standard legal texts, little is known about the way in which prisoners’ rights to family life are exercised in practical terms. How do prisoners’ families and prison personnel understand, interpret, and use the law? How do their interactions affect the implementation of legal regulations? Based on a field survey in France, this article reveals the reasoning behind prison officers’ law enforcement decisions. Such decisions are by no means arbitrary, but stem from a contextual assessment of the situation with which they are confronted. This article also highlights the different ways in which prisoners’ families make use of their rights, which are rarely defended through collective action, given the difficulty for this population category of forming a social group.