When nonviolent activists design an action that poses a dilemma for oppo-nents—for example whether to allow protesters to achieve their objectiveor to use force against them with consequent bad publicity—this is calleda dilemma action. These sorts of actions have been discussed among acti-vists and in activist writings, but not systematically analyzed. We presenta preliminary classification of different aspects of dilemma actions andapply it to three case studies: the 1930 salt march in India, a jail-in usedin the Norwegian total resistance movement in the 1980s, and the free-dom flotillas to Gaza in 2010 and 2011. In addition to defining what isthe core of a dilemma action, we identify five factors that can make thedilemma more difficult for opponents to “solve.” Dilemma actions derivesome of their effectiveness from careful planning and creativity that pushopponents in unaccustomed directions.