In an approach to managing obfuscation of regulated sensitive data, one or more computer processors detect content for display on a computing device. One or more computer processors analyze the content for sensitive data. One or more computer processors retrieve one or more applicable regulations, where the regulations are associated with displaying sensitive data. One or more computer processors determine a location on the display for obfuscating the sensitive data in the content, based on the retrieved one or more applicable regulations. One or more computer processors identify one or more context rules applicable to the sensitive data in the content. One or more computer processors determine the one or more context rules override the one or more applicable regulations. One or more computer processors display the sensitive data in the content.