Improvised Explosive Device (IED) incidents account for the majority of combat deaths among Canadian Forces (CF) in Afghanistan. The problem of training for safe and early IED detection in-theatre is exacerbated by insurgent forces that observe counter-IED efforts and quickly adapt to them. Further, the average Afghan tour of duty for Canadian Forces is much less than a year in duration, severely limiting institutional memory in the combat unit. Recently-arrived troops are much less likely to identify an IED threat in time to prevent an event than are those with several months in-country. This paper reports on the front-end analysis, design, development and evaluation of a game-based training application that distills the experiences and lessons learned of just-returned CF troops to present immersive, scenario-based training. The Counter-IED Immersive Training Environment (CIITE) employs VBS2, intelligent agents and speech interaction. We summarize the design principles and technical implementation, and present empirical findings from a pilot evaluation, to include measures of operational relevance, usability, and perceived training potential. For operational relevance, Canadian troops recently returned from Afghanistan participated in shaping the scenarios. We also worked with CF Land Forces Directorate Training Services (LFDTS) group to develop survey instruments aimed at shaping the training to meet the expectations and background of the CF target audience. For usability and attitudes toward training value, ten soldiers with at least one tour of duty in Afghanistan each completed two scenarios and provided survey data to assess attitudes toward the fidelity of the information contained in the scenarios and the perceived benefit to soldiers about to be deployed. We present findings from this pilot study and discuss what these preliminary results suggest about the training approach employed in this program.