This case study deals with the development and implementation of two online art courses. It outlines the concerns of the faculty member responsible for these courses and those of the instructional designer assisting him. The key design issues deal with the management of copyright material available via the Internet, the difficulty of implementing innovative educational strategies, and the use of new Web 2.0 tools. This case study highlights the challenges of the relationship between an instructional designer and a professor in the context of instructional and technological innovation.