This chapter considers post-socialist or postcommunist transformations as a subtype and historical wave of imitative societal transformations, i.e., system changes taking the form of disruptive, accelerated, and politically steered modernization projects which follow successful models of society in the framework of global hegemonies. Focusing on an international comparative overview of post-socialist change in the Second World system, i.e., the countries and union republics within the Soviet Empire, the chapter begins with a discussion of dynamics and factors of state socialism’s decline. Subsequently, it problematizes key dimensions, actors, and dilemmatic processes of the transitional phase in the narrow sense, concentrating on the political and economic spheres. Finally, the chapter deals with the long-term period of structuration and its ambivalent character, which includes a discussion of varieties and innovative aspects of postcommunism as well as post-transformative challenges.