My dissertation investigates Perestroika, a period of intense reform in the Soviet Union that began under Mikhail Gorbachev in 1985 and ended when the Soviet Union collapsed in 1991. This study reframes new government policies as a response to what reformers perceived as a moral crisis that they set out to solve by reinvigorating socialism. This dissertation then asks one central question: How did Soviet people respond to reform? I answer this question through a microhistorical case study of the Red October Chocolate Factory in Moscow, which offers the opportunity to trace responses across the social spectrum, from the highest members of the Politburo to rank-and-file workers and their children. The primary analytical apparatus of this study is the concept of engagement. Drawing on ideas of historians Jochen Hellbeck and Igal Halfin developed for an earlier period in Soviet history, this concept allows us to consider a multiplicity of responses to reform, including belief and disbelief, support and criticism, as part of a rigorous conversation between the Soviet state and people. This study extends existing literature that frames Perestroika as an economic initiative aimed to revamp a flagging economy by emphasizing the moral and humanistic center of reform. Further, it offers a detailed empirical investigation of popular responses to reform that includes but is not limited to high ranking officials and the intelligentsia. It challenges the argument that the Soviet Union collapsed because nobody believed or cared about socialist. Instead, this study suggests that the Soviet collapse was an unintended consequence of reform. This dissertation offers a way to think about continuities across the 1991 quandary and the ways in which the last years of Soviet history remain relevant today, particularly with respect to contemporary moral discourse in the Russian Federation.