Enterprise needs to process customer data for providing tailored services to them, however, the data often includes sensitive and personally identifiable information. This leads to a difficult situation wherein the enterprise has to balance the necessity to process the sensitive data with the requirement to safeguard its privacy. The problem is more prominent in legacy applications with almost no privacy controls in place. A well-studied technique to retrofit legacy application is to mask sensitive content before it is rendered on the screen using path based methods. In this work we show the gap in the existing state of art and describe a dynamic system which utilizes a context to perform locality based searching and masking of sensitive content.