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The chapter covers three vital aspects of selecting IT sourcing models: conducting a comprehensive cost-benefit analysis, assessing vendor capabilities and expertise, and aligning IT sourcing models with the organization’s culture and values. It outlines the methodical approach necessary to undertake a cost-benefit analysis, enumerating the direct and indirect costs and tangible and intangible benefits involved. It then moves on to elaborate on the key areas for vendor assessment including technical capabilities, industry experience, service level agreements, and adaptability. Finally, the importance of aligning IT sourcing decisions with the organization’s culture and values is underscored, with emphasis on promoting cultural integration for a successful partnership.