Contextual Design is a methodology for developing information systems from a rich understanding of customer work practice. This chapter considers how Contextual Design can be applied to educational software development and how Contextual Design might interact with Instructional Systems Design (ISD). Following a brief overview of ISD, I describe Contextual Design and provide a detailed case study of its application to educational software development — to the design of an online tool for music listening and analysis in undergraduate and graduate music education. I conclude with some reflections on the relevance of Contextual Design to instructional designers.