Environmental disputes occur frequently, particularly in contexts of poor natural resource management and vague law, but while some of these disputes end quickly without fatalities, some escalate to violence or become persistent contentious juggernauts that are increasingly hard to end. What makes a sequence of contentious events more likely to escalate to violence or persistent contention? This dissertation argues that strategic interactions in the form of violence, government behavior, and scarcity type signal the likelihood that the government will support claimant demands, and thus determine whether desperate claimants must escalate to maintain access to environmental goods and services necessary for survival. I also argue that there are material constraints from current repression and violence, and that timing matters. I test these propositions in two sets of logistic regressions, using new subnational data from Indonesia and an in-depth case study. I find empirical support for the claims that prior violence, structural scarcity, and past government repression increase the likelihood of continued contention. The same variables except for past government repression also increase the likelihood of violence. Current government repression reduced the likelihood of both violence and continued contention, but as time passed it exerted a more pernicious effect on violence and resolution. In other words, timing mattered, although dense events were surprisingly less likely to yield violence or continued contention. This project indicated that there are significant opportunities for reducing the likelihood of violence and persistent contention through policy changes, potentially reducing the suffering of individuals, the destruction of natural environments, and drains on the capability of the state.