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The chapter explores the challenges of integrating Agile and DevOps methodologies with IT sourcing strategies, particularly with external vendors. It outlines key difficulties, including cultural compatibility, speed and flexibility, skills and expertise, integration and collaboration, measurement and accountability, and security and compliance. It also provides strategies for aligning IT sourcing with Agile and DevOps, emphasizing cultural compatibility, skills and expertise, collaboration, adaptive contracts, Agile vendor management, security incorporation, and Agile-friendly metrics. The final section provides considerations for selecting Agile and DevOps vendors, including their expertise, cultural fit, communication skills, adaptability, technical competency, security measures, and performance metrics.