One of management objectives when dealing with Web services (or related Internet strategies) is to cut business costs. Information systems (IS) literature has to date focussed primarily on research related to direct costs, that is, costs that occur in IS budgets (Bannister & Remenyi, 1999). IS research into strategic planning on the other hand has underestimated the expenditure of hidden costs as part of the adoption of new information technology systems within organisations. One of the difficulties regularly faced by IS investment planners is the identification, and thus management of, hidden indirect costs, for example, human indirect costs (Mohamed & Irani, 2002). This chapter addresses the increasing need to identify the “critical indirect human costs” associated with IS adoption as a fundamental part of the cost estimation of strategic planning when adopting IS. The research adopts an indirect human cost taxonomy proposed by Mohamed, Irani, and Baldwin (2002) associated with management, employee, finance, and maintenance divisions of an organisation.