Transition from war to peace often leads to new challenges. Conflict scholars suggest that these challenges lead groups to be unable to commit credibly and suggest mechanisms for decreasing the fear of being the victim, and increasing the costs, of reneging. However, international law and international political economy scholars debate the utility of making agreements flexible. This paper argues that provisions intended to increase the flexibility of agreements are detrimental to implementation because they operate under the assumption that groups are in a repeated game, and because they can lead to an even more severe commitment problem. Using a newly collected dataset on civil war cease-fire agreements, duration analyses suggest agreements with more flexibility-enhancing provisions exhibit a higher likelihood of violations. Although provisions calling for third-party enforcement – a mechanism for reducing fear and increasing costs – seem to decrease the likelihood of violations, this effect disappears when flexibility-enhancing provisions are considered.