This article presents a comparative analysis of aspectual usage in imperatives in Slavic, building upon Benacchio’s cross-Slavic analysis (2010) and Šatunovskij’s (2009) analysis of Russian. It analyzes imperatives as a parameter of usage in the general east-west Slavic aspect division established by Dickey (2000), and argues that differences in the aspectual systems in the eastern and western groups of Slavic produce different pragmatic effects of aspectual usage in imperatives. Across Slavic, perfective imperatives communicate a request for the addressee perform an action to completion. Additionally, East Slavic perfective imperatives communicate a request to first make the choice to perform an action and then to perform it (this unusual semantic profile is typical of East Slavic, which has an aspectual system unusually sensitive to discourse factors). In contrast, imperfective imperatives refer to open-ended processes and repeated events. Further, in the case, of completed events, they communicate that there is no need for the listener to first make the choice. Such imperfective imperatives are divided into subjective cases (the speaker makes the choice) and intersubjective cases (the speaker knows/infers that the listener has already made the choice). Most Slavic languages have developed the subjective type to some degree, whereas the intersubjective type has been developed primarily in East Slavic, and to a lesser extent in Polish and Bulgarian.