Systems, methods and computer storage mediums automatically enabling private browsing of a web page are described herein. Embodiments of the present disclosure relate to equipping a web browser with the ability to automatically open web pages in a privacy mode based on content of the web pages so that a user is not required to manually activate the privacy mode. The web browser is able to identify characteristics of the content provided by the web pages by analyzing the web pages for content that increases the likelihood that the user may require that the web page be opened in the privacy mode.