Many information resource managers have learned to be proactive in today’s highly competitive business environment. However, limited financial resources and many uncertainties require them to maximize their shareholders’ equity while controlling the risks incurred at an acceptable level. As the unprecedented development in information technology continuously produces great opportunities that are usually associated with significant uncertainties, technology adoption and planning become more and more crucial to companies in the information era. In this study, we attempt to evaluate IT investment opportunities from a new perspective, namely, the real options theory. Its advantage over other capital budgeting methods like static discounted cash flow analysis has been widely recognized in analyzing the strategic investment decision under uncertainties (Amram & Kulatilaka, 1999; Luehrman, 1998a, 1998b). Smith and McCardle (1998, 1999) further show that option pricing approach can be integrated into standard decision analysis framework to get the best of the both worlds. In fact, some previous IS researches have recognized the fact that many IT investment projects in the uncertain world possess some option-like characteristics (Clemsons, 1991; Dos Santos, 1991; Kumar, 1996). Recently, Benaroth and Kauffman (1999) and Taudes, Feurstein and Mild (2000) have applied the real options theory to real-world business cases and evaluated this approach’s merits as a tool for IT investment planning.