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E-commerce creates opportunities for companies to implement internal and external connections. This establishes new capabilities to meet market needs and changes the way business can be conducted through the redefinition of rules and roles in the extended enterprise. The literature suggests that the emergence of Internet / Web based communities of common interest accelerates this shift towards the concept of the extended enterprise by enabling enterprises to align within a series of 'value networks' against other groups of enterprises. A collaborative approach and shared benefits are among the crucial factors which bind these value networks of closely integrated business communities. This study investigates the cultural and organisational context of implementing e-commerce to support business to business collaborative relationships. Using primarily qualitative and exploratory methods, various interrelationships are explored through two in depth case studies. The research approach is structured by underpinning theories, predominantly transaction cost economics, and informed by key findings from the literature search of the topic domain. The research itself is based on the assumption that collaborative e-commerce cannot be considered in a vacuum and that a holistic perspective is required, particularly in considering the socio-political and relational aspects of such inter-organisational systems. The work undertaken therefore seeks to identify the interrelationships between the IT, organisational and business aspects of collaborative business to business relationships. The research concludes that a number of interdependent factors are key in implementing e-commerce to support collaborative relationships. Foremost among these are the redesign of processes and practices, common information interchange standards and support, a consultative approach based on mutual trust, the sharing of benefits and a willingness to learn and to adopt a 'network' perspective. The findings are encapsulated into an e-commerce/collaborative relationship framework developed by incorporating key findings from the case studies, as well as themes from the literature. This framework may be a useful tool for analysis in other case studies and could be refined and enhanced by further such research.