Systems and methods are provided for automatically monitoring a compliance of web pages and graphical user interfaces with governmental and self-regulatory privacy and security policies. In accordance with one implementation, a method is provided that comprises instructing the execution of an operation on content associated with at least one web page is generated. The operation may include at least one of (i) a scanning operation that generates forensic data corresponding to the web page or (ii) an analytical operation that analyzes at least a portion of the forensic data corresponding to the web page. The method further comprises obtaining output data associated with the executed operation, and generating information indicative of a compliance of the web page with at least one of a privacy regulation or a security regulation, the information being generated based on the output data.