What does the International Monetary Fund's (IMF) response to the financial crisis say about its past and future roles in Sub-Saharan Africa (SSA)? To find answers, this article explores the tensions between the "old" Fund's efforts to entrench "sound" macroeconomic policies and the "new" IMF's plans to insure its members against global volatility. The paper outlines the risks associated with the pursuit of IMF policy advice, reviews the Fund's engagement in Angola and Mozambique, and discusses how these experiences reflect on its future role. The case studies suggest that whilst countries that work with the Fund are more resilient than those that go at it alone, resilience comes at the cost of a more ambitious developmental state—not because the Fund hampers aspirations, but because it cannot leverage ambition. The study concludes that rather than glossing over the political cost of risk insurance, the IMF should target its assistance to governments that are prepared to make, explain, and follow-up on the difficult choices.