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Often, the creation of new military doctrines or technologies lead to claims that they are likely to be “more” or “less” escalatory than the systems that they are replacing. However, measuring “more” or “less” escalation is rarely a focus of international relations research. Traditionally, conflict escalation has been inductively modeled as a linear or geometric curve representing an escalation “ladder” (Kahn 1965; Haney 2016). In this paper, I use a series of experiments—using both wargaming and survey methods—to examine how respondents conceptualize and “act out” escalation during crisis scenario. I also track the transition probabilities from one conflict state to another to consider likelihood of conflicts to escalate given specific crisis characteristics. In the process, the paper seeks to make a theoretical contribution to the field’s understanding of conflict escalation and a methodological contribution to nascent field of experimental wargaming.