We evaluated the efficacy of a computer-based situation awareness (SA) measurement system for training dismounted infantry SA in an urban terrain virtual reality (VR) simulation. Based on past research, we hypothesized that the SA measures would be sensitive to individual (squad leader) differences, and that the frequency of specific probes would reveal differences in critical SA requirements among scenarios. Three infantry squads performed multiple trials across two different scenarios. A confederate platoon leader posed probes to squad leaders during trials and experts made ratings afterward. Results revealed squad leaders had similar responses to probes, despite differences in combat experience. Analysis of probe frequency revealed different high priority SA elements and decisions for each scenario. The SA behavior and communication ratings revealed differences among squads, which trended with experience. Measures of SA were also consistent across the test scenario as a result of similar mission types and task difficulties. We discuss the implication of our findings for future research and theory within this area.