This chapter presents an exploration of the design and methods of two instantiations of authentic learning tasks in online learning environments. The first case employs a service learning orientation involving a distance learning project taught to students in four sites in two countries, while the second case is of a multimedia-based learning environment employing a scenario to engage students in realistic, simulated learning activities. The two approaches are examined through reference to characteristics of authentic tasks. The chapter demonstrates a range of possibilities for the instructor interested in more informed design of technology-based learning environments in higher education, and in particular, the design and creation of authentic learning tasks.