As traditional news organizations have struggled to adapt their content and financial models to networked information environments, and community journalism startups have begun to test a variety of new business and organization models, the line between journalistic and commercial expression has become opaque. This article examines the challenges emerging, twenty-first-century media organizations pose to how the courts have historically understood press and commercial-related speech protections. The article analyzes how the Supreme Court of the United States has rationalized its standards for press and commercial safeguards and considers how the Court has decided in recent cases involving citizen publishers who claimed protections historically reserved for traditional journalists. Ultimately, the article draws the building blocks from these ideas to propose how courts can separate the two types of communication in the twenty-first century. In doing so, the article also proposes ways in which such fledgling organizations can ensure they remain journalistic in nature.