The chapter discusses the challenges organizations face when transitioning to agile methodologies. It highlights the need for a careful assessment of readiness, as agile methodologies differ significantly from traditional, plan-driven approaches. Agile methodologies, such as extreme programming (XP), feature-driven development, and scrum, emphasize flexibility, collaboration, and rapid feedback, which can be challenging for organizations accustomed to structured, process-centric methods. The transition involves changes in organizational culture, management practices, and technology, requiring significant investment and time. Key issues include managing organizational culture, adapting knowledge management practices, fostering collaborative decision-making, and ensuring the availability of competent personnel. The chapter also addresses the need for appropriate tools and training to support agile practices. Overall, while agile methodologies offer benefits, organizations must carefully evaluate their readiness and address these challenges to successfully adopt them.The chapter discusses the challenges organizations face when transitioning to agile methodologies. It highlights the need for a careful assessment of readiness, as agile methodologies differ significantly from traditional, plan-driven approaches. Agile methodologies, such as extreme programming (XP), feature-driven development, and scrum, emphasize flexibility, collaboration, and rapid feedback, which can be challenging for organizations accustomed to structured, process-centric methods. The transition involves changes in organizational culture, management practices, and technology, requiring significant investment and time. Key issues include managing organizational culture, adapting knowledge management practices, fostering collaborative decision-making, and ensuring the availability of competent personnel. The chapter also addresses the need for appropriate tools and training to support agile practices. Overall, while agile methodologies offer benefits, organizations must carefully evaluate their readiness and address these challenges to successfully adopt them.