Though “journalism” is an amorphous term capable of various meanings, its traditional media are familiar. Yet, if the progression in media from print to radio to broadcast and cable teaches a lesson, it is that dissemination technology is rarely stagnant. As the seemingly endless procession of new media made possible by digital communication continues, the manner by which works of journalism are disseminated is also changing. Whether this evolution in media creates a better informed and more capable citizenry is a fair subject for debate. What is less debatable is that the blossoming of digital media is testing legal frameworks, particularly in the realm of journalistic privileges. Shield laws, also known as reporters’ privileges, have existed in the United States for more than a century as a way to foster the free flow of information. While questions have long persisted about how to properly administer shield law protection, the rapid pace of media evolution is exposing the shortcomings in many existing statutory constructions and interpretations. This Recent Development casts a critical look at a 2011 Oregon shield law decision Obsidian Financial Group, LLC v. Cox. Presenting Obsidian as an example of problematic statutory drafting and interpretation, this Recent Development seeks to introduce a more sustainable, medium-neutral model for shield law protection.