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The purpose of this chapter is to provide organisations with a better understanding of how they can manage rapidly developing information and communication technology, and particularly wireless networks that have evolved into several technological standards in recent years. Case analyses of two large organisations, called here Metro University and Urban Healthcare Centre, demonstrated collective patterns of how organisational legitimacy was changed. More specifically organisational legitimacy, in relation to wireless networks and IT management, was often enhanced by the recognition and/or appreciation from three major groups of stakeholders: external customers who were normally prospective users, internal customers who were the existing users, and the IT staff members who provided services to the user groups. Our empirical findings suggest that certain social values such as prospective customers' recognition, internal customers' satisfaction, and existing IT staff members' appreciation might help shape an organisation's long turn image and legitimacy. They might not provide immediate profitability and growth, but their effects could be sustained over time and help organisations to survive and ultimately thrive. Organisations situated in today's rapidly changing IT and wireless environment might thus need to reconsider how to better capture various social values derived from IT and wireless network projects, and in turn help legitimise their innovative status that might ultimately ensure long-lasting survival.