The first part of this chapter presents the results of a systematic literature review on Agile Software Development (ASD) challenges as are reported in implementation and adoption cases. The data only considers the concrete evidences of surfaced problems mainly according to work experience and case study articles. The results are analyzed so that types, nature and intensity of the problems are determined and, compared to each other, within three major classifications of “large organizations”, “distributed settings” and “both large and distributed environments”. The analysis reveals that, in ASD, common organizational and managerial issues have been replaced by communication and collaboration problems. The second part uses the results of the part one as a frame of analysis to render more interpretations e.g. signifying that non-agility preconceptions are the root of a majority of problematic projects. Besides, mediating between agile projects and traditional forms of management, and, economic governance are two major rival approaches that are emerging in response to these challenges.
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