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In this paper we will advance a perspective that links business network analysis to inter-organizational systems (IOS) uptake, starting with an analytic framework to characterize both different types of electronic business to business interactions (via the web) as well as the network of business relationships in which they are used. In order to see whether inter-organizational IT systems and business networks (mis)match they are compared on two dimensions: 'mode of interaction' (relational versus transactional) and 'nature of coordination' (emergent versus directive). The study analyses two Australian agricultural cooperatives 'Capgrains' and 'Bluegum'. The transactional focus and directive control of Capgrains' online ordering system did not match with the relational interaction and emergent coordination that was common in their network of business relationships, resulting in a mismatch and low level of use of the system. The Bluegum's group communication system much better matched with the business relationships in the cooperative and higher use of the IOS. Indicating a positive relation between match and uptake of the IOS.