There is a growing awareness and interest in the issues of accountability and transparency in the pursuit of digital privacy. In previous work, we asserted that systems needed to be “policy aware” and able to compute the likely compliance of any digital transaction with the associated privacy policies (law, rule, or contract). This paper focuses on one critical step in respecting privacy in a digital environment, that of understanding the context associated with each digital transaction. For any individual transaction, the pivotal fact may be context information about the data, the party seeking to use it, the specific action to be taken, or the associated rules. We believe that the granularity of semantic web representation is well suited to this challenge and we support this position in the paper.