Despite attracting headlines and hype, insurgents rarely win. Even when they claim territory and threaten governmental writ, they typically face a military backlash too powerful to withstand. States struggle with addressing the political roots of such movements, and their military efforts mostly just 'mow the grass'; yet, for the insurgent, the grass is nonetheless mowed--and the armed project must start over. This is the insurgent's dilemma: the difficulty of asserting oneself, of violently challenging authority, and of establishing sustainable power. In the face of this dilemma, some insurgents are learning new ways to ply their trade. With subversion, spin and disinformation claiming centre stage, insurgency is being reinvented, to exploit the vulnerabilities of our times and gain new strategic salience for tomorrow. As the most promising approaches are refined and repurposed, what we think of as counterinsurgency will also need to change. The Insurgent's Dilemma explores three particularly adaptive strategies and their implications for response. These emerging strategies target the state where it is weak and sap its power, sometimes without it noticing. There are options for response, but fresh thinking is urgently needed--about society, legitimacy and political violence itself.