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We address the problem of transforming natural language descriptions of contracts into a form that is suitable for automating various contract management functions. We investigate two complementary methods that can be used to achieve this. One method is suitable for the contract specification phase - to specify expected behaviour of contracting parties so that they can satisfy policies stated in a contract. This method also allows for checking aspects of contract consistency as well as flexible integration of internal organisational policies with the contract policies. Another method targets the contact run-time phase - for monitoring behaviour of parties to the contract and other aspects of contract performance. When combined, these two methods provide a basis to support an increasing level of automation of many mundane contract activities, while allowing humans to be involved in ultimate decision making.