Throughout modern business history, contract has been used as an organizational technology that holds counterparties in formal or legally binding agreements. The proliferation of contract prompted the emergence of professional contract managers who played an important but relatively peripheral role applying situational awareness to the practice of compliance and business relationship management. As more complex organizational forms emerge (outsourcing, supply chains and enterprise IS), contract has come to be seen as a standard coordination device whose foundational assumptions are taken for granted. In this study, we draw attention to two different ways of designing the organizational technology of contract: a process-oriented approach and a marketbased valuation of contract. Both approaches promise to provide management information by offering a form of calculability but we argue distort organizational awareness. Our conclusion is that a more developed notion of organizational awareness is needed supported by an alternative conceptualization of contract as a technology of connectedness.