ITS 2000 is the fifth international conference on Intelligent Tutoring Systems. The preceding conferences were organized in Montreal in 1988, 1992, and 1996. These conferences were so strongly supported by the international community that it was decided to hold them every two years. ITS’98 was organized by Carol Redfield and Valerie Shute and held in San Antonio, Texas. The program committee included members from 13 countries. They received 140 papers (110 full papers and 30 young researchers papers) from 21 countries. As with any international conference whose proceedings serve as a reference for the field, the program committee faced the demanding task of selecting papers from a particularly high quality set of submissions. This proceedings volume contains 61 papers selected by the program committee from the 110 papers submitted. They were presented at the conference, along with six invited lectures from well known speakers. The papers cover a wide range of subjects including architectures for ITS, teaching and learning strategies, authoring systems, learning environments, instructional designs, cognitive approaches, student modeling, distributed learning environments, evaluation of instructional systems, cooperative systems, Web based training systems, intelligent agents, agent based tutoring systems, intelligent multimedia and hypermedia systems, interface design, and intelligent distance learning.