In this paper we address how external factors shape government decisions to break or uphold contracts, specifically focusing on how economic shocks and support from multilateral financial institutions shape leader decisions to expropriate from investors. Contrary to conventional wisdom and much of the existing scholarship, we argue that governments are less likely to expropriate from investors during periods of economic crisis since governments become more sensitive to the reputational costs of expropriating. We also argue that governments are sensitive to the levers other governments may use to punish for expropriation, such as withholding IMF and World Bank funding. We test these theories using a dataset of investment expropriations and case studies of thirty-four investment disputes that were resolved pre-claim. Our econometric analysis suggests that expropriations of foreign investment are less common during periods of crisis, and that countries under IMF agreements or borrowing from the World Bank are less likely to expropriate. Our thirty-four case studies, which substantiate the role of government reputation and multilateral pressure, support our statistical results.