This chapter provides an exploration of the reasons why a Canadian Federal Court refused to compel five Internet service providers to disclose the identities of twenty nine ISP subscribers alleged to have been engaged in P2P file-sharing. The authors argue that there are important lessons to be learned from the decision, particularly in the area of online privacy, including the possibility that the decision may lead to powerful though unintended consequences. At the intersection of digital copyright enforcement and privacy, the Court’s decision could have the ironic effect of encouraging more powerful private-sector surveillance of our online activities, which would likely result in a technological backlash by some to ensure that Internet users have even more impenetrable anonymous places to roam. Consequently, the authors encourage the Court to further develop its analysis of how, when and why the compelled disclosure of identity by third party intermediaries should be ordered by including as an element in the analysis a broader-based public interest in privacy.