© 2016 Academy of Criminal Justice Sciences. Given the increasing number of prisoners serving life sentences in England and Wales, and the increasing average length of these sentences, it is surprising that so little attention has been paid to the experiences and effects of such sanctions. This article describes how prisoners serving very long sentences from an early age adapt over time to their circumstances. In particular, it focuses on the transition between the early and subsequent stages of such sentences, specifically, the ways that these prisoners adapt to the sentence, manage time, come to terms with their offense, shift their conception of control, make their sentence constructive, and find wider meaning in and from their predicament. Our argument is that most prisoners demonstrate a shift from a form of agency that is reactive to one that is productive, as they learn to “swim with”, rather than against, the tide of their situation.