This article studies the case of the sanctions against the Russian war on the Ukraine in 2022 against the background of four major and well-documented historical sanction episodes: (1) the anti-Apartheid sanctions of the 1980s, (2) the sanctions against the Iraqi occupation of Kuwait in 1990, (3) the sanctions against Iranian nuclear capabilities and (4) the US and EU sanctions against the Russian annexation of the Crimea. Two cases (South Africa and Iran) have a comparatively low probability of success based on pre-sanction trade linkage between sender and target and the target’s regime type (the autocracy score). The key to understanding their success is in the banking channel (debt-crisis and international payment system sanctions) and the behaviour of the private sector (divestment and over-compliance). The failure of the sanctions against Iraq underscores the importance of regime type and the need for a viable exit strategy and shows that some decision-makers cannot be influenced with economic hardship. The 2014 sanctions against Russia illustrate the comparative vulnerability of the European democracies and their weakness in organizing comprehensive sanctions that bite. Given the increased Russian resilience, the increasingly autocratic nature of President Putin’s government, the credibility of his 2014 tit-for-tat strategy and the failure of European democracies to implement appropriate strong and broad-based measures, smart and targeted sanctions are unlikely to influence the Kremlin’s calculus. The European Union could only influence that calculus by restoring its reputation as a credible applicant of strong sanctions, including an embargo on capital goods and a boycott of Russian energy.