We seek to theorize postsocialist theory by questioning why so many fear and avoid its utilization. As we argue, postsocialist theory, much like postcolonial theory, is a useful tool in assessing the contemporary political conjuncture, particularly in provincializing capitalism, the state, and anticommunism. Thinking with postsocialism, we suggest, allows a crucial mapping across spatiotemporal scales, connecting seemingly disparate times, sites, and politics, which may or may not include ex-state-socialist countries. Rather than simply serving as a spatial description of ex-socialist countries and urbanisms, we see postsocialism as a theoretically helpful analytic for apprehending and criticizing accounts of a universal global West, McCarthyism 2.0, the renewed Red Scare, and the entanglement of liberal and fascist capitalisms. Postsocialist theory in this way creates analytic spaces of critique regarding neoliberal practices, urban and otherwise, abetting in the crafting of an informed anti-anti-communism. As we show, the reshaping of the so-called First, Second, and Third Worlds after the fall of the Berlin Wall overlapped with analytic interventions aimed at foregrounding connections between postcolonialism and postsocialism in a universal post-Cold War world. We also illustrate the spatiotemporal tensions between confining and universalizing postsocialist theory through a discussion of ex-socialist cities and their various morphologies. This helps us in rendering paths toward thinking with postsocialism for future research, transgressing the oft-calcified enclosures of both the former Iron Curtain and the state in our imagining and materializing anticapitalist urban geographies.