A unique system and method that facilitate automatic tracking of user data and providing on-demand site or merchant reputation information is provided. The system and method involve monitoring user input such as by keystrokes over a period of time and forming a long continuous string of characters. The string of characters can be monitored for repeating substrings or non-repeating substrings that indicate sensitive user information such as SSN or credit card number (CCN). The substrings can be displayed to the user in a digest form and order according to frequency of occurrence, for example. Thus, the user can readily view where and when their sensitive information has been entered. In addition, the typing of certain substrings such as CCNs or other sensitive field data can trigger a reputation service to retrieve the reputation data for the current site or merchant to mitigate dealing with fraudulent sites or merchants.