Abstract: A web content inspection system is configured to monitor the activity of web content tags and cookies during interaction with web content. Monitoring may include automated simulations of web content interaction that occur in a virtual browser or environment, as well as real-time monitoring of web content interactions that occur with actual users through a browser or other application. Features may include monitoring of the creation of cookies, writing information to cookies, and reading information from cookies, as well as associating cookies with the tags or scripts that affect them, and displaying such associations in a hierarchical form that indicates the sequence of actions that led to the cookie activity. Other features include monitoring for the presence of high-risk information in plain-text or encoded formats, within a URL or other portion of web content. Other features include determination of overall risk associated with a tag based on its activities.