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Sustainability of competitive advantage may be achieved by leveraging unique firm attributes with information technology to realize long-term performance gains. Information systems that cannot sustain competitive impact have only transient strategic value or may offer negative value if matched by a superior response by competitors. A research review of sustainability was conducted that resulted in the development of a framework depicting factors effecting sustainable competitive advantage. This study evaluates longitudinal changes in performance measures of 30 firms that have been cited as “classic" cases of strategic use of information technology. The results of this analysis indicate that not all of these classic cases can be touted as “sustained winners." Differences among strategic “sustainers" and “non-sustainers" were formally tested to determine those firm and/or industry factors that may be antecedents to sustained IT competitive advantage. Results indicate that managers must do more than simply assess the uniqueness or availability of emerging technological innovations in developing strategic IT plans. Specifically, the establishment of technological base along with substantial capital availability seem to be important prerequisites for “technologically derived" sustainability. Recognizing the need for a stronger prescriptive orientation to strategic IS, future research is outlined in an effort to develop a comprehensive framework that would link combinations of sustainability factors to actual performance.