Experts agree that formal strategic IT plans should not only be done, but they should alsobe revised regularly at least on a yearly basis (Barrett & Greene, 2001). Reed (2003) citesdata from the Government Performance Project that high-performing governments tendto update their plans one or more times during a year. Raumer (2001) points out that withthe cutbacks in governmental budgets, IT projects are no longer rubber stamped but mustmake their business case and argues that the strategic planning process is needed to setsound priorities. The term business case refers to a case based on solid business reasonssuch as increased revenues and/or decreased costs that are expected to improve theeffectiveness and efficiency of the organization and may be contrasted with changes fornon-business reasons such as for prestige and “keeping up with technology.” Failureto plan adequately has led to serious problems. For example, Ward (2003) has argued thatorganizations must plan their intranets or the intranets will die. He cites examples ofintranets that have failed and have to be restructured frequently because they were done“on a whim” of management with no clear direction and became political “footballs.”In this chapter, I discuss the key issues and problems encountered in planning forinformation technology. In particular, I will focus on the logic behind prescriptions to doplanning and the challenges and complexities that occur in planning for IT. I also seekto explain why planning is often not done at all or not done according to the recommen-dations laid out by experts.