Professor Armstrong earned his bachelor's and master's degrees from The University of Texas at Austin and his law degree, with high honors, from the University of Texas School of Law. There he was Managing Editor of the Texas International Law Journal and a member of the Chancellors honorary society. He served for one year as a law clerk to Senior Circuit Judge John Minor Wisdom of the U.S. Court of Appeals for the Fifth Circuit. Following his clerkship, Professor Armstrong practiced with the law firm of Howrey, Simon, Arnold & White in Washington, D.C. He earned a Master of Laws degree from Harvard Law School.
During his career in private practice, Professor Armstrong specialized in Supreme Court and appellate litigation and was an active member of the firm's pro bono committee. During the Monica Lewinsky investigation in 1998, he defended the Office of the President of the United States in executive and attorney-client privilege litigation arising from the Independent Counsel's issuance of grand jury subpoenas to attorneys in the White House Counsel's Office. Professor Armstrong's other primary areas of experience in practice included administrative law, antitrust law and trade regulatory issues, labor arbitration, and government contract disputes. He also represented indigent death row inmates in Virginia and Georgia in state and federal habeas corpus proceedings, and participated in several Supreme Court cases on behalf of organizations serving persons with disabilities.
Before joining the College of Law faculty, Professor Armstrong worked as a Clinical Teaching Fellow for the Berkman Center for Internet & Society at Harvard Law School. In that capacity, he served as Assistant Director of the Berkman Center's Clinical Program in Cyberlaw and co-taught the course "Internet & Society: The Technologies and Politics of Control," at the Harvard Extension School.
Professor Armstrong is the co-author, along with Professor William McGeveran of the University of Minnesota Law School and Professor Derek Bambauer of Wayne State University Law School, of Info/Law, a weblog focusing on legal issues arising from the domain of high technology and the Internet. His research interests include copyright and other intellectual property law, digital rights management and other legal issues arising from networked communications technologies, licensing and other issues surrounding free and open-source software, and statutory interpretation.