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When nonviolent activists design an action that poses a dilemma for opponents—for example whether to allow protesters to achieve their objective or to use force against them with consequent bad publicity—this is called a dilemma action. These sorts of actions have been discussed among activists and in activist writings, but not systematically analyzed. We present a preliminary classification of different aspects of dilemma actions and apply it to three case studies: the 1930 salt march in India, a jail-in used in the Norwegian total resistance movement in the 1980s, and the freedom flotillas to Gaza in 2010 and 2011. In addition to defining what is the core of a dilemma action, we identify five factors that can make the dilemma more difficult for opponents to “solve.” Dilemma actions derive some of their effectiveness from careful planning and creativity that push opponents in unaccustomed directions.