The paper aims to provide an overview of the current issues in IT investments management. Topics such as IT investments evaluation, the reflexive relationship between the business context and IT investments are analyzed in detail. Also, the paper analyzes the impact of time over IT investments as well as the causes that lead to IT projects failure. A synthesis is carried out among the arguments regarding the IT Investments Paradox. Different evaluation methods are exposed along with their practical usage. The results are presented both from an economical perspective and from a technical one.