Organizations spend substantial capital budgets on IT investment in order to achieve potential competitive advantages. However, IT investments are characterized with complexity, uncertainty, and risk. These attributes make appropriate IT investment decision making a challenging task. Decision analysis cycle methodology is a conceptual framework that facilitates achieving clarity of action in difficult decision problems. In the present study, this methodology is explained and applied on an imaging system investment of a mortgage bank to investigate how it can tackle complexity, risk and uncertainty in IT investment decisions.