Countersurveillance has been acknowledged as an empowering act of civil society that can keep the government in check. With its increasing popularity in academic and popular circles comes a need to better understand when countersurveillance brings a positive outcome and when it backfires. This question is particularly important when countersurveillance is used to bring about a change in policy implementation. Using data from interviews, peace organizations’ reports, and open sources, this paper examines peace movements’ countersurveillance of West Bank checkpoints, exploring the intended and unintended consequences of countersurveillance in this setting. This paper argues that when countersurveillance breaks powerholders’ understanding of social order, it can trigger a harsh response that can render it counterproductive. Contrarily, when countersurveillance operates within the boundaries of this understanding of order, the likelihood of a successful outcome increases.