Classroom learning improves significantly when students participate in structured learning activities in small groups of peers. As the U.S. military moves from schoolhouse instruction to web-based distance learning, the student loses this important contact with other students. The educational value of student collaboration has led to the use of conventional groupware tools, such as chat and email, in distance learning environments. While these tools can enrich learning, they require at least two participants who are available at the same time and cannot guarantee the quality of assistance. Students in a web-based environment require high-caliber instructional support on demand. A simulated learning companion, acting as a peer in a distance learning environment ensures the availability of a collaborator and encourages the student to learn collaboratively, while drawing upon the advantages of distance learning. The learning companion we designed for PRAXIS encourages the student to reflect on and articulate past actions, and to discuss future intentions and their consequences.