This essay expands upon an earlier work (Grodzinsky and Tavani, 2005) in which we analyzed the implications of the Verizon v RIAA case for P2P Networks vis-à-vis concerns affecting personal privacy and intellectual property. In the present essay we revisit some of the concerns surrounding this case by analyzing the intellectual property and privacy issues that emerged in the MGM Studios v. Grokster case. These two cases illustrate some of the key tensions that exist between privacy and property interests in cyberspace. In our analysis, we contrast Digital Rights Management (DRM) and Interoperability and we examine some newer distribution models of sharing over P2P networks. We also analyze some privacy implications in the two cases in light of the theory of privacy as contextual integrity (Nissenbaum, 2004).