Mediating privacy mechanisms on the client-side will aid in next generation e-transformation as they enhance users' perception of online trust in an organization. We propose a collaboration, between a context agent and a P3P agent, which results in the application of context-specific privacy rules during a user's electronic commerce transaction with an organization's Web site or Web service. The context agent manages dynamic changes of the context, inform the user about the current privacy-related context for decision support, and automatically generate user preferences. Fully compliant to the P3P privacy platform, the context management system supports the storage, index, retrieval, and switch of user contexts. Test cases using real web sites' P3P policies demonstrate the functionality and utility of the context manager agent. Delays are in the range of less than one second to 7 seconds depending on activities such as a context switch or P3P comparison.