–––In the last decade, the phenomenon of peer-to-peer file-sharing and its various legal aspects have been dealt with extensively by legal scholarship. The purpose of this Article is to take a closer inspection of several particular legal aspects that are related to peer-to-peer file-sharing as a comparative, social, economic, and cultural phenomenon. The Article begins by providing critical comparative analysis of distinct paradigms that different legal systems have offered regarding the question of third party liability for copyright infringements that occur through peer-to-peer file-sharing platforms. The Article then presents three focal policy considerations that should serve as copyright law’s compass in the context of peer-to-peer file-sharing: (a) adopting a requirement of compliance between the legal liability of third parties and copyright law’s exemptions and limitations regime; (b) striking a socially desired allocation of risk between positive and negative externalities that peer-to-peer file-sharing platforms tend to generate; (c) understanding the unique distributional concerns that are raised by legal regulation of peer-to-peer file-sharing platforms, especially when taking into account the nature of such platforms as a novel emerging speech resource that society has to decide upon its allocation. The last part of the Article focuses on some of the next generation legal questions that peer-to-peer networks are already beginning to give rise to, including the legal liability of internet service providers for managing peer-to-peer traffic through active caching and routing applications.