The relationship between IS flexibility, IT capability, and IT-Business alignment is well recognized in both theoretical and practitioner’s literature. However, there is much less understanding upon what factors these relationships might be contingent. At the same time, there is growing evidence that both internal and external factors may be important and influential. Therefore, to enhance the existing IT-Business alignment research, this study presents and empirically tests a moderator framework of IS flexibility, IT capability, and IT-Business alignment. The influence of both endogenous (organizational size, strategic orientation) and exogenous (environmental uncertainty, industry environment) moderators is considered. The research confirmed the positive relationships between IT flexibility, IT capability, and IT-business alignment. System infrastructure, connectivity, and IT relationship to organizational tasks showed individual statistically significant influences. Environmental uncertainty and, to a lesser degree, firm’s strategic orientation demonstrated significant moderating effects. Theoretical and practical implications of the findings are discussed.
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