The Internet of Things (IoT) and Big Data are making it impractical for people to keep up with the many different ways in which their data can potentially be collected and processed. What is needed is a new, more scalable paradigm that empowers users to regain appropriate control over their data. We envision personalized privacy assistants as intelligent agents capable of learning the privacy preferences of their users over time, semi-automatically configuring many settings, and making many privacy decisions on their behalf. Through targeted interactions, privacy assistants will help their users better appreciate the ramifications associated with the processing of their data, and empower them to control such processing in an intuitive and effective manner. This includes selectively alerting users about practices they may not feel comfortable with, confirming with users privacy settings the assistants are not sure how to configure, refining models of their user’s preferences over time.