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The 2013–2014 Revolution in Ukraine has spurred a boom in civic anti-corruption initiatives across Ukraine. There is as yet little consolidated understanding of how effective these initiatives are and what explains variation in effectiveness. Insights from academic and practitioner literature suggest that factors associated with success in anti-corruption activism fall under three broad categories: environmental factors, advocacy strategies of civil society organizations, and their organizational characteristics. Drawing on a comprehensive study of anti-corruption activism in the regions of Ukraine, this article asks how these insights relate to anti-corruption activism in the regions of Ukraine. We find that anti-corruption initiatives generally face two key dilemmas: insufficient capacity in terms and financial and human resources, and the absence of a credible base of support. Anti-Corruption organizations that are most effective tend to be those that convincingly solve either one of these two dilemmas. In addition, we find that political will among local authorities is an important conducive factor to the effectiveness of anti-corruption activism. The article also discusses the implications of our findings for practitioners of international assistance.