This paper examines how financial regulation and institutional quality affect the probability of a banking crisis using a panel of 132 countries over the period 1999-2011. We find that the probability of a financial crisis increases moving from low to medium levels of regulation and decreases from medium to high levels of regulation. This relationship is sensitive to the institutional quality and creates a liberalization trap for “happy mediums”: only countries endowed with good institutions can undertake a liberalization process. This effect is larger for European Union (and Eurozone) members than other countries. As heterogeneity in institutional quality generates also different preferences, international agreements on banking regulation are hard to achieve, especially in Europe. Our results are consistent with several robustness econometric exercises.