Throughout its 20-year history, Debian had to face a number of legal issues, in all fields of the so (improperly) called "Intellectual Property". From trademarks to patents, from copyright to export control and embargoes, Debian didn't miss a single pesky issue. In this talk we review some of the most relevant legal issues that Debian has faced in recent years and how the project has responded to them. Doing so is a chance not only to share legal best practices with other Free Software communities, but also to highlight the policy annoyances that widespread legal systems imposes on radical Free Software communities such as Debian.