In the wake of the financial crisis, the United States government introduced a new large-scale initiative to address homelessness. The policy mandate is marked by both an unprecedented increase in federal funding and a dramatic reallocation of resources toward Housing First, a service model emphasizing immediate housing subsidization. Although this service paradigm has received support from a sizeable literature, our knowledge of its success to date has been limited. This paper sheds light on the unobservable or unmeasured costs of this new centralized approach to ending homelessness. I argue that federal homelessness policy under the Housing First approach 1) generates resource misallocation, 2) exacerbates the Samaritan’s dilemma, and 3) invites rent seeking.