Since 1987, Copyleft licensing has been the primary strategy of the FOSS community to guarantee users' rights to copy, share, modify, redistribute, and reinstall modified versions of their software. In our earliest days, we naïvely thought that the GPL would work like magic pixie dust; we'd sprinkle it on our code, and our code would remain free as in freedom. The reality check that we've received over the last 35 years has been painful on this issue. While this talk will cover the few huge successes in copyleft enforcement that have lead to real improvements to the rights and freedoms of users, we'll also face frankly the compromises made and false paths taken in the earliest days, that have now led to a simple but unfortunate fact: almost every Linux-based device for sale on the market today does not comply with Linux's license (the GPLv2). This talk will not only discuss the primary past GPL enforcement efforts around the world, but also provide a whirlwind tour of how copyleft came to work in practice, how we wished it had worked, and discuss ideas, suggestions, and plans for the future strategies in copyleft that, informed by this history, are our best hope for software freedom and rights. Have ever wondered how FOSS was actually was supposed stay FOSS for the long term? Have you ever been unsure or confused why — in a world where Linux is on nearly every device — most people cannot actually run an alternative OS build on their device? This talk will leave you informed on these questions and prepared to participate in the next policy steps our community must take to bring back software freedom and rights to the next generation of FOSS users, activists and developers.