In this chapter, we explore the significant challenges relating to investment in IT business. Information technology does not in itself deliver business value. We highlight the complexities that are often ignored in management of IT projects. If the management system in an organization is ineffective, then installing information technologies does not constitute a ‘magic wand’ that will generate prosperity. It can only generate value if attention is paid to the design of the system for use at the same time that technological systems are developed. The authors explore how IT benefits require attention from management generally and show that investment in IT projects cannot be left to ‘IT experts’ alone. We point out that undue reliance on rational planning is unsatisfactory, as it ignores contextual dependencies in organizational life. Criteria by which the success/failure of projects is to be judged must go beyond a focus on timescales, budgets, and ‘requirement specifications.’ We suggest that the criteria need to be expanded to embrace usefulness of resultant systems, as perceived by organizational staff as they attempt to use them in carrying out their work.