Contextual design is a human-centered methodology for designing information systems from a rich understanding of customer work practice (Beyer & Holtzblatt, 1998). This article explores the application of contextual design to online learning systems development. Beginning with definitions of Instructional Systems Design (ISD) and contextual design, this chapter then offers a detailed description of the latter, and concludes by considering its relevance to the design of online learning technologies. To avoid confusion, it is important to understand the differing backgrounds of ISD and contextual design. ISD models are process models for the development of instruction or instructional systems (ASTD, 1988; Dick & Carey, 1996; Kemp, Morrison & Ross, 1998). In this context, “systems” refer to the interrelatedness of all parts of an instructional program and the attempt of the development process to account for the many parts and their interdependencies. Contextual design grew out of very different soil—a soil in which “systems” means “information systems;” that is, computers, software and related technologies. As a computer system design method, contextual design focuses on how best to design systems—hardware and software—to meet customers’ needs. While these needs may include learning or training, the concern is less with learning how to do something than with actually doing it— quickly, cheaply, effectively. With instructional design, content is nearly always critical. With contextual design, as will be seen, work practice is critical.