The Enterprise Information Security Management (EISM) system aims to semi-automatically estimate the sensitivity of enterprise data through advanced content analysis and business process mining. We demonstrate a proof-of-concept of EISM that crawls all the files in a personal computer and estimates the sensitivity of individual files and the overall sensitivity level of the computer. The system can identify 11 different personally identifiable information (PII) types and 11 sensitive data categories, and estimate data sensitivity based on the identified sensitive information in the data. Furthermore, the tool produces the evidences of the discovered sensitive information including the surrounding context in the document to help users understand what kinds of sensitive information are stored in their computer. The evidences allow users can easily redact the sensitive information or move it to a more secure location. Thus, this system can be used as a privacy enhancing tool as well as a security tool. © 2011 ACM.