Fostering the synergy among learner, task and technology to create innovative and immersive distance learning environments runs counter to the widespread practice of incorporating traditional classroom pedagogical strategies into web-based delivery of courses. The most widely accepted model of online higher education appears to be one of reductionism, whereby learning management systems facilitate the design of easily digested packets of information, usually assessed by discrete stand-alone tests and academic assignments. This paper describes a model of authentic tasks that can assist in designing environments of increased rather than reduced complexity. It provides a robust framework for the design of online courses, based on the work of theorists and researchers in situated learning and authentic learning. It describes the characteristics of a task’s design that facilitates the requirements of an entire course of study being readily satisfied by its completion, where the students make the important decisions about why, how, and in what order they investigate a problem. The paper describes several learning environments that were investigated in depth in the study and explores the synergies that exist between the learners, tasks and technology engaged in authentic learning settings. The paper leads readers to a conceptual understanding of the role of authentic tasks in supporting knowledge construction and meaningful learning, and illustrates the principles of authentic task design for online learning environments.