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The digital age brought many challenges for copyright law. While offering enticing new formats for the production and dissemination of copyright content, it also raised the specter of large scale digital piracy. Since the end of the 20th century, content industries have reeled to keep up with technological developments that offer significant promise as well as threats of large scale piracy. There has always been some tension between promoting innovation in content creation and promoting innovation in technologies that enable the enjoyment of copyright works, such as photocopiers, audio tape recorders, video tape recorders, and peer-to-peer file sharing systems. The manufacturers and distributors of these technologies have had to tread a fine line in their marketing and distribution efforts to avoid liability for secondary copyright infringement liability based on direct infringements by their customers. To this list of technologies, we may now add Internet search engines and online payment systems. This paper considers ways in which copyright law has addressed the secondary liability question in an increasingly digital marketplace. It suggests that the realities of this marketplace necessitate a new look at broader policy issues underlying digital copyright law more generally in order to meaningfully address questions of secondary liability online.