Training advanced combat profiling skills presents a wide range of challenges in any setting, especially a computer-based training environment. Specifically, these challenges surround training higher-order perceptual-cognitive skills, such as interpreting subtle and often ambiguous cues in dynamic contexts without the experiential framework of a real-world setting. The US Marine Corps' Combat Hunter curriculum was designed specifically to train these skills through advanced combat profiling and tracking methods, along with the supporting perceptual-cognitive knowledge. The core curriculum has been implemented into conventional face-to-face instruction across the US Marine Corps. In an effort to support this training, a computer-based pre-training system was commissioned. Despite the widespread advantages of computer-based training, the lack of real-time instructor facilitation presents a variety of challenges. This paper discusses some of these challenges focusing primarily on one of the key components of Combat Hunter, combat profiling. Also, it addresses issues such as how to present a variety of cues within a given context, how to offer relevant feedback on the analysis of unclear indicators in a given environment, and how to familiarize trainees with the importance of cultural context. This paper further discusses strategies, that when implemented, take learners through a progression of cue detection and interpretation activities. Ultimately, this computer-based training system is intended to enable preparation for training in advanced combat profiling by focusing on the interpretation of cues within a given context and supporting key prerequisite declarative knowledge. Trainees will have the core skills to excel in the practical application and hands-on instruction of the corresponding face-to-face Combat Hunter course.