Previous research suggests that individuals faced with risky choices seek ways to actively reduce their risks. The risk defusing operators that are identified through these searches can be used to prevent or compensate for negative outcomes. Although several factors that affect RDO selection have been identified, they are limited to static decisions conducted during descriptive tasks. The factors that influence RDO selection in dynamically unfolding environments are unknown, and the relationship between task characteristics and RDO selection has yet to be (...) mapped. We used a videogame environment to conduct two experiments to address these issues and found that experienced losses impacted risk mitigation strategy: when the task was difficult, participants experienced greater losses and were more likely to select preventive RDOs. Additionally, risk mitigation behavior stabilized as participants gained experience with the task and could be shifted by making an RDO easier to use. Exploratory analyses suggested that these risk mitigation choices were not driven by judgments of difficulty, even though participants’ JODs were accurate and aligned with task difficulty. This research suggests that while people seek preventive RDOs when tasks are difficult and risky, risk mitigation strategy is shaped by experienced losses; decision makers do not use JODs to anticipate future risks and inform risk mitigation decisions. (shrink)