In this study, we aim to enable learners to act based on their own judgment during disasters by practicing evacuation drills. We developed a system called “ES3” that supports learning to make good judgments. This system presents a virtual situation based on the evacuation drill scenarios and urges learners to make judgments and take action. As a result of practicing disaster-prevention drills using the system in a high school, it was confirmed that learners judged the situations by themselves. From the results of the subjective survey, changes were noticed in the ability of learners to make consciousness judgments and recognize dangerous outdoor places and places that could be evacuated, all of which were achieved through the drills. The results of this study reveal that learners have become interested in disasters and have developed an awareness of the need to act proactively as a result of the judgment drills.