This chapter uses the theory of loose coupling to explain failure in the adoption of an information technology aimed at improving collaboration across one organization’s internal boundaries. The research details an interpretive case study of a single organization, MacGregor Crane, in which relatively autonomous individuals are only loosely connected in terms of their daily interactions. The company implemented Lotus Notes© in an attempt to increase collaboration. However, this effort failed because employees in various units, particularly engineering, were reluctant to share information across unit boundaries. In light of these findings, it is suggested that the successful implementation of a collaborative IT within a loosely coupled organization should involve the reconsideration of the organizational members’ roles and functions.