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The lack of knowledge on 1) how Web technologies support the business strategies of an organization and 2) how Web technologies enhance organizational performance are gaps in the existing literature that may account for the inability of the majority of Web-based firms to leverage their investments in Web technologies. To address these knowledge gaps, a theoretical lens is constructed from five core logics in organizational literature that represent the different possible ways of enhancing organizational performance. Applying the lens to analyze the case of a successful Singaporean dotcom, the ways through which Web technologies enhance organizational performance are identified. Specifically, our study reveals that the process through which Web technologies enhance organizational performance is contingent on the state of the organizational environment. When the environment is in a state of equilibrium, Web technologies can enhance organizational performance by facilitating the attainment of competitive advantage through three distinct mechanisms: the logics of positioning, leverage, and opportunity. Conversely, when the environment is in a state of revolution, Web technologies can give rise to performance gains by supporting the attainment of legitimacy through two distinct mechanisms: the logics of optimality and social congruence.