Over the last two decades, the Internet and its associated innovations have rapidly altered the way people around the world communicate, distribute and access information, and live their daily lives. Courts have grappled with the legal implications of these changes, often struggling with the contours and characterization of the technology as well as the application of constitutional provisions and principles. Judge M. Margaret McKeown of the United States Court of Appeals for the Ninth Circuit has had a close-up view of many of these Internet-era innovations and the ways the courts have addressed them. In this Article, adapted from her October 2013 Roger L. Shidler Lecture at the University of Washington School of Law, Judge McKeown offers her retrospective thoughts on the ways courts have handled constitutional issues in Internet cases. She also discusses some of the challenges currently facing courts and legislators alike as the U.S. legal system incorporates and accommodates Internet-based technologies and the societal, commercial, governmental, and relational changes they spawn