The United States and many of its coalition partners have initiated a broad program of reform aimed at transforming their defensive capabilities to take advantage of recent advances in technologies and to meet emerging security challenges. Progress to date, however, has been mixed in terms of the ability of the DoD redefine itself as an information age organization and in terms of the DoD’s capacity to deliver transformational capabilities to war fighters. This chapter examines questions regarding our ability to guide, direct and control large scale organizational change. I suggest that transformational efforts can be viewed through the lens of the agent-structure, which posits that that social change is the outcome of a complex dialectic between human agents and social structures. I argue that our understanding of this dialectic may be significantly enhanced if we examine the theoretical and empirical insights gained from the study of complex adaptive systems (CAS).