Business-to-business (B2B) information technology (IT) use is transforming B2B trading relationships in distribution channels. Nevertheless, the assessment of B2B IT effectiveness is complex and challenging. It depends not only on how well IT use is integrated with trading processes but also on the dynamics of strategic stakes between firms. It is influenced by the commitment of leadership to trading relationship management and IT investments. This paper presents a model of how B2B IT use impacts cooperative trading processes and how IT effectiveness is assessed considering strategic stake levels and top management communication between two firms. Using survey data, it reports the results of data analyses where the impact of B2B IT use appears differently between suppliers and retailers. The results also suggest that strategic stakes and top management communication drive how B2B IT use is implemented and evaluated.