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Territorial conflict is back; indeed, it never truly left. Given a resurgence in conflict over territory and new interest in territorial acquisition, it is worth investigating both how states attempt to acquire new territory, and how states try to protect their existing territory. Understanding the interests, incentives, and bargaining capability of groups engaged in conflict over territory is thus vital for explaining outcomes. In particular, this paper investigates the role of the less successful state in conflict. States succeeding in conflict often have the opportunity and capability to pursue additional territorial acquisition before the conflict ends. Possessing the territory at the end of conflict increases the bargaining position of the successful state. Given this, what can the trailing state do to deter the successful state from pursuing additional territory? Are there actions the losing state can take, even if it lacks the capability to fully resist? Building on the author’s prior work, this paper examines the options available to the trailing or less successful state in conflict. How can the trailing state impact the successful state’s calculus of the benefit of additional territory? How can it improve its bargaining position? The paper considers whether the trailing state could manipulate the risk of future conflict, the involvement of third-parties, or perceptions of reputation in trying to protect its territory, and uses case studies to investigate the dynamics at play.