This chapter presents a perspective on web technologies acquisition, utilization, organization change and transformation grounded in Gidden’s theory of structuration, i.e., a contextualist analysis. A contextualist analysis is processually based, emergent, situational, and holistic, marrying both theory and practice. This chapter’s paradigm affords a substantive analytical tool to the practitioner for understanding and managing not only web-based IT acquisition, utilization and organization change, but all IT-based recursive, organization changes and transformations. Organization change associated with IT acquisition and utilization is posited as concomitantly necessary. Organization change is recursive, dynamic, multilevel, and nonlinear, i.e., an “enacted” environment. Ever present organization opposing values are treated dialectically, i.e. as paradox, operating simultaneously. The nature of the resolution of such paradox enabled/inhibits reframing, i.e., organization transformation and change. The paradigm presented defines an organization change continuum, delineating four organization responses to contradiction and paradox. The chapter explicates organization culture and organization learning as systemic, multiplicative metaforce underpinnings of organization change and sociocognitively-based, recursive, structurational processual dynamics. The chapter discusses use of the IT acquisition and utilization paradigm for organization diagnosis as well as customization of organization change interventions. The chapter suggests further typologically-based research venues.