People are in violation of copyright law when they copy or distribute copyrighted material without the consent of the copyright holder. Enforcement of digital copyright violations are continually thwarted by the large population of users who participate in online file sharing and the rapid technological innovation that usually keeps the file-sharing community one-step ahead of the law. Learning from the court case which revealed the mistakes of Napster and other early litigation involving digital copyright material, several technologies currently exist in the nexus of these loopholes, including: (1) Usenet (e.g., Giganews); (2) decentralized peer-to-peer filesharing (e.g., Limewire); and (3) extraterritorial one-click file-hosting (e.g., Rapidshare). This short essay examines copyright violations involving each of these separate technologies, as well as some of the issues that serve to undermine the enforcement of copyright law on the digital frontier.