A configurable, customizable privacy protecting software agent operates on behalf of a user to control the dissemination and use of the user's personal data. The software agent is guided by a personal/corporate privacy charter specified by the user (or an enterprise manager), which charter is adapted dynamically based on user and site conditions. The agent engages with digital service provider (DSP) sites/apps on users' behalf, and notifies them of privacy incompatibilities, issues, etc. associated with the DSPs, along with recommended alternatives if available or possible. The agent can also tag user data and monitor unauthorized uses to report on DSP compliance with user specified policies.