This article presents the results of a collaborative ethnographic inquiry in contemporary Sofia and Caracas. Combining historical research and ethnography, we compare the ways in which a former and a current left-wing regime treat urban squatting. In both cities, squatters tend to be poor families escaping homelessness. In Sofia, “squatters”—usually of Roma origin—inhabit unregulated spaces deemed illegal after 1989. In Caracas, homeless families have been officially encouraged to squat but not declared legal occupants. A historical comparison shows both socialist governments turn a blind eye to extralegal housing practices. Benign, informal housing arrangements function to display solidarity with marginalized groups as a form of popular legitimacy. Yet, without formalized state protection, such arrangements produced a “surplus” population, vulnerable vis-à-vis global processes of capitalist reorganization.