Expressing contractual agreements electronically potentially allows agents to automatically perform functions surrounding contract use: establish- ment, fulfilment, renegotiation etc. For such automation to be used for real busi- ness concerns, there needs to be a high level of trust in the agent-based system. While there has been much research on simulating trust between agents, there are areas where such trust is harder to establish. In particular, contract proposals may come from parties that an agent has had no prior interaction with and, in competitive business-to-business environments, little reputation information may be available. In human practice, trust in a proposed contract is determined in part from the content of the proposal itself, and the similarity of the content to that of prior contracts, executed to varying degrees of success. In this paper, we argue that such analysis is also appropriate in automated systems, and to provide it we need systems to record salient details of prior contract use and algorithms for as- sessing proposals on their content.We use provenance technology to provide the former and detail algorithms for measuring contract success and similarity for the latter, applying them to an aerospace case study.