Although academic scholarship has addressed how city governments have responded to declining housing affordability in the aftermath of the crisis, few studies have done so from a comparative perspective. Filling this gap in the literature, this paper studies two distinctive, but nevertheless commonly ‘unaffordable’ city contexts: Amsterdam and Miami. First, it reconstructs how both cities responded differently to otherwise common housing challenges by prioritizing public interventionist (Amsterdam) and public entrepreneurial (Miami) housing strategies. Second, it unravels how the underlying logic and market outcomes of both approaches have nevertheless become similar. To varying degrees, both cases reveal an (i) progressive shift in social housing provision from lower-income groups towards middle-income groups, and (ii) the increased importance of market logic within the affordable housing sector at large. Despite good intentions, the paper concludes that both cities struggle with addressing affordable housing needs in what are, after all, neoliberal housing contexts. In the absence of greater state commitments, local willingness to contest housing financialization runs into the limits of affordable housing governance.