This article examines the unpredictable consequences of escalated repression on the dynamics of contention. By examining sequences of interactions among contenders in the course of one conflict, analysis traces pathways through which the escalation of repression impacts activists and protest targets in ways that seemingly go against the intentions of repressive agents. Three types of outcomes of repression are identified: a worse situation for protest targets; triggered radicalization; and a “chilling effect” on lawful protest. This article contributes by demonstrating a temporally sensitive approach that traces how certain pathways combine to produce these unintended outcomes. The empirical case studied is the life cycle (1999–2014) of the British conflict between the Stop Huntingdon Animal Cruelty animal rights campaign and the Huntingdon Life Sciences corporation, which also involved the government, criminal justice agencies, and private businesses.