This Article examines the evolution of the law governing libel suits against anonymous “John Doe” defendants based on Internet speech. Between 1999 and 2009, courts crafted new First Amendment doctrines to protect Internet speakers from having their anonymity automatically stripped away upon the filing of a libel action. Courts also adapted existing First Amendment protections for hyperbole, satire, and other non-factual speech to protect the distinctive discourse of Internet message boards. Despite these positive developments, the current state of the law is unsatisfactory. Because the scope of protection for anonymous Internet speech varies greatly by jurisdiction, resourceful plaintiffs can make strategic use of libel law to silence their critics. Meanwhile, plaintiffs who are truly harmed by cybersmears will find little effective recourse in libel law. Though disheartening, the current state of the law may be a testament to the difficulty of balancing speech and reputation in the Internet age.