Our 1998 paper “Encouraging Student Reflection and Articulation using a Learning Companion” (Goodman et al. 1998) was a stepping stone in the progression of learning companions for intelligent tutoring systems (ITS). A simulated learning companion, acting as a peer in an intelligent tutoring environment ensures the availability of a collaborator and encourages the student to learn collaboratively, while drawing upon the instructional advantages that ITSs provide. This paper is a commentary on our 1998 paper, reflecting on that research and some of the subsequent relevant research by others and us since then in Learning Companions, Intelligent Tutoring Systems, and Collaborative Learning.