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We explore the challenge of selecting the best among a set of alternative IT investments. Solving this problem is important since the difference between alternative investment options may be drastic in terms of business results, both positive and negative. The resulting model takes as input a set of investment alternatives and a parameterized description of IT services, and provides as output a Preference Index for each alternative. The solution takes into account such characteristics as epistemic and aleatory uncertainty as well as the decision maker's attitude toward risk. Through a case study and a sensitivity analysis, we conclude that the model is useful in practice and robust; we also describe its domain of validity.