Hoyerswerda, Germany's fastest-shrinking city, faces problems with the future that seem initially unrelated to the past and yet excite manifold conflicting accounts of it. The multiple and conflicting temporal references employed by Hoyerswerdians indicate that the temporal regime of postsocialism is accompanied, if not overcome, by the temporal framework of shrinkage. By reintroducing the analytical domain of the future, I show that local temporal knowledge practices are not historically predetermined by a homogenous postsocialist culture or by particular generational experiences. Rather, they exhibit what I call temporal complexity and temporal flexibility-creative uses of a variety of coexisting temporal references. My ethnographic material illustrates how such expressions of different forms of temporal reasoning structure social relations within and between different generations. Corresponding social groups are not simply divided by age, but are united through shared and heavily disputed negotiations of the post-Cold War era's contemporary crisis.