Information systems / information technology (hereafter referred to as IS/IT) now represents substantial financial investment for many organisations. Information systems and technology managers have found it increasingly difficult to justify rising IS/IT expenditures. They are often under immense pressure to find a way to measure the contribution of their organisations’ IS/IT investments to business performance, as well as to find reliable ways to ensure that the business benefits from IS/IT investments are actually realised. This problem has become more complex as the nature of IS/IT investments and the benefits they can deliver has evolved over time and has changed rapidly. Furthermore, the evaluation of these IS/IT investments is a complex tangle of financial, organisational, social, procedural and technical threads, many of which are currently either avoided or dealt with ineffectively by organizations (Pervan, 1998). In this chapter we will learn what is IS/IT investment evaluation and benefits management, discuss some of the problems and challenges in this area, review some of the better known approaches to this problem, acknowledge some of the leading authors in the area, and conclude with a summary of the current status of the field and some possible directions for future research and practice.