Insurance for damage caused by public unrest became popular in post-1918 Central Europe and proved to be a profitable business, but one that became increasingly problematic because of the role of fascist regimes in promoting civil commotion. This article addresses some of the experiences of insurance companies, especially the Munich Reinsurance Company, when trying to manage policies covering political unrest and riot in Italy, Germany and Spain between 1922 and 1941. In the case of Italy in 1922, the new fascist regime forced the insurers to pay for damages caused by the Squadri. In Germany, the insurers were forced to assume a fictitious liability for damages done to the Jews in the Pogrom of November 1938. In Spain, Franco forced the insurance companies to treat Civil War damages as a civil commotion and make payouts despite their strenuous objections. These experiences demonstrated that civil commotion insurance was most safely marketed in democracies that provided enough unrest but also law and order to make it worthwhile.