In this highly technology dependent and knowledge intensive economy, organizations were forced to change the way of doing business and move form bricks to clicks to survive and compete. Accordingly, organizations have to adopt the suitable IT solutions that fit their mission, vision, and objectives. One way to achieve that is IT outsourcing either entirely or partially. This is a part of a comprehensive study that investigates the IT outsourcing risk management practice in Syria, identifies the causes of IT outsourcing projects failures and what kind of knowledge is used when identifying risks, and finally proposes a conceptual framework that achieves integrated view of risk management regarding IT outsourcing projects. To achieve that, the researcher followed DRM as a research methodology starting from “what is usually done” moving toward “what can be done most realistically,” which is presented in detail in this chapter and resulted in the proposed framework.