In this chapter, I argue that what is past is prologue—that the colonial foundations of punishment in the Anglophone Caribbean actively structure contemporary penal systems. Using path dependence theory, I show how institutional mechanisms serve as positive feedback and function to reinforce punitive continuity, while the judiciary has emerged as a potential site of disruption, serving as negative feedback. By integrating postcolonial scholarship, subdisciplines of critical criminology and sociolegal insights, I specify how colonial logics persist and identify avenues for rupture. Ultimately, I conclude that only when we acknowledge that our current understanding of what penal reform might look like is determined by the evolutionary changes of the past, will we have the freedom to radically reimagine punishment in the Anglophone Caribbean.