For more than two decades since the rise of the World Wide Web, the “Notice and Choice” framework has been the governing practice for the disclosure of online privacy practices. The emergence of new forms of user interactions, such as voice, and the enforcement of new regulations, such as the EU’s recent General Data Protection Regulation (GDPR), promise to change this privacy landscape drastically. This paper discusses the challenges towards providing the privacy stakeholders with privacy awareness and control in this changing landscape. We will also present our recent research on utilizing Machine learning to analyze privacy policies and settings.