There are now many educational research and technology projects reporting a variety of outcomes and lessons learned with regard to how to effectively integrate technology into learning and instruction. What can we learn from these projects and experiences? Is there a clear and coherent instructional design framework for technology-enhanced learning environments? What are the most promising approaches to instructional design? Are there particular tools that can assist? What kinds of evaluations will insure that the process of designing such environments will become progressively more effective? These are the questions explored in this chapter. The discussion includes a short review of the possibilities afforded by new technologies, with special emphasis on collaborative tele-learning and Web-based simulations. After illustrating the rich and diverse kinds of interactions now possible in Web-based settings, we shall argue that instructional design is more critical than ever before. It is not the case that technology has simplified instructional planning. Quite the contrary; new technologies have made the design of effective learning environments even more challenging than before. While our concept of learning remains relatively intact, the settings in which instruction can and does occur and the kinds of resources which can be brought to support learning in those various settings has changed dramatically. As a consequence, the subject of this chapter is relatively unexplored territory, and the findings and conclusions suggested herein should be regarded as tentative and preliminary.