In this chapter, the authors present the automatization of a technique for identifying the risks that may affect software acquisition projects. The proposed technique can have an impact in two software acquisition areas: 1) acquisition software contract for: Fully Developed (FD) software, Modified-Off-The-Shelf (MOTS) software, and Commercial-Off-The-Shelf (COTS) software; and 2) information technology services contract, which can be a result of using the required technological tools for the operation of any organization. In both cases, it is indispensable to manage and address (track) the risks that may affect the success of any project type mentioned above.