After 40 years, we still know very little about how state repression influences political dissent. In fact, to date, every possible relationship, including no influence, has been found. We argue that part of the problem concerns the current practice of treating every repressive event as if it were substantively equivalent, differentiated only by scope (large/small) or type (violent/nonviolent). We advance existing work by arguing that the influence of repression is contingent on when it occurs within the temporal sequences of political conflict. Using new events data on the “Troubles” in Northern Ireland from 1968 to 1974, results show that when dissent has been decreasing in the recent past, repressive action inspires an increase in dissident action. When dissent has been increasing, however, repression has the opposite effect, decreasing challenging activity. These results provide important insights into resolving a recurrent puzzle within the conflict-repression nexus as well as understanding the interaction between government and dissident behavior.