Scenario-based training systems pose an especially difficult challenge for an intelligent tutoring system (ITS). In addition to the basic problems of deciding when to intervene and what guidance to provide, the ITS must decide whether to give guidance directly (e.g., a hint message), indirectly through positive/negative results in the scenario, or to delay guidance until a post-scenario review session. There are a number of factors that an adaptive ITS should consider and we use self-report survey instruments to investigate the relationship between traits, learning strategies, expectations, learner behaviors derived from log files, post-use perceptions of the system, and pre-test and post-test results. We use the ELITE Lite Counseling training system as a testbed for our experiments. This system uses virtual role players to allow learners to practice leadership counseling skills, and is in use at the United States Military Academy (USMA). This paper analyzes two data sets. We collected data from local university students, a non-military population of roughly the same age as USMA Cadets using the system. For these local participants, we could administer surveys and pre-tests and post-tests, and collect log files recording clicks made while using ELITE Lite. The second data set comes from USMA itself but is limited to log files. In both populations, the ITS’s hints are effective at boosting scenario performance, and for the university students, the overall experience promoted learning, and survey results suggest that higher levels of organization in study habits may lead to greater learning with ELITE Lite. For the USMA Cadets, ELITE Lite is part of their Military Leadership course rather than an experiment, which could explain why we found higher scenario performance on average than the non-military population, and more use of the post-scenario review feature.