Information systems and technology are critical to today’s business, especially in current ebusiness environment. The information systems curriculum, IS2002, not only places emphasis on technical discipline-specific knowledge, it also stresses the importance to train students in an authentic context. Authentic learning employs authentic context reflecting the way knowledge is used in real world situations. However students often encounter difficulty in achieving desired learning outcome in this type of real world problem-based learning environment. This paper describes the design of a series of learning scaffoldings to make authentic learning and group work effective.