This paper examines the characteristics and value of designed instruction grounded in the constructivist theory. It also attempts to connect the theory to the prevailing technology paradigms to establish an alignment between pedagogical and technological considerations in support of the assumptions arising from constructivism. Distance learning provides a unique context in which to infuse constructivist principles where learners are expected to function as self-motivated, self-directed, interactive, collaborative participants in their learning experiences by virtue of their physical location. Hence, the aim of this paper is to provide a clear link between the theoretical principles of constructivism, the construction of technology-supported learning environments, and the practice of distance education. The questions driving the argument in this paper include: What do constructivist perspectives offer instructional design and practice? What do computing technologies offer? And what do the two afford in combination? In particular, how do the two combine to transform distance learning from a highly industrialized mass production model to one that emphasizes subjective construction of knowledge and meaning derived from individual experiences.