Learning environments, where students are immersed in some type of communications sphere (text or graphics) to promote learning has been discussed for over two decades. With the introduction and growing availability of personal computers supporting high-quality graphics capability, the type of learning environment research has shifted away form text to graphics. A number of projects have undertaken to design and study the digital learning environments ranging from 2D environments with such projects as the Inquiry Learning Forum, Math Forum, and the original MOOSE Crossing to 3D environments like River City, Quest Atlantis, or Chalk House. Studies on both the design and learning outcomes of these environments are opening up a number of avenues for working towards improvements in student learning, engagement, and satisfaction that make them and exciting focus for theorists and researchers. Beyond the 'wow” factor of these environments there are also struggles that accompany any innovation, and this chapter examines both some of the successes and challenges to designing and using these educational environments.