The nature of informal economies is structured by conflict between governmental strategies of confinement, to places, times, and how things are done, and the transgression of these confines by informal actors in pursuit of survival or advantage. We examine the influential development program of formalization in the context of these conflicts. Informality can be formalized in two ways, by eradication and by regularization. Building on our past ethnographic research on informality, we use released confidential Hong Kong colonial government documents to explore the informal discussions among policy makers about how to respond to informal practices, and how their understanding of street vendors influences their chose of confinement strategies. While insisting on eradication for squatters, various forms of regularization were attempted for street vendors.