This essay expounds on Raphael Cohen-Almagor’s recent book, Confronting the Internet’s Dark Side, Moral and Social Responsibility on the Free Highway, and advocates placing narrow limitations on hate speech posted to social media websites. The Internet is a limitless platform for information and data sharing. It is, in addition, however, a low-cost, high-speed dissemination mechanism that facilitates the spreading of hate speech including violent and virtual threats. Indictment and prosecution for social media posts that transgress from opinion to inciteful hate speech are appropriate in limited circumstances. This article uses various real-world examples to explore when limitations on Internet-based hate speech are appropriate. In October 2015, twenty thousand Israelis joined a civil lawsuit filed against Facebook in the Supreme Court for the State of New York. Led by the civil rights organization, Shurat HaDin, the suit alleges Facebook allows Palestinian extremists to openly recruit and train terrorists to plan violent attacks calling for the murder of Israeli Jews through their Facebook pages. The suit raises important questions, amongst them: When should the government initiate similar suits to impose criminal sanctions for targeted hate speech posted to Facebook? What constitute effective restrictions on social media that also balance society’s need for robust dialogue and free communication, subject to limitations reflecting a need for order and respect among people? Our essay progresses in four stages. First, we examine philosophical origins of free speech and the historical foundations of free speech in the United States. Second, we provide an overview of American free speech jurisprudence. Third, we address particular jurisprudence that provides a framework for imposing limitations on free speech in the context of social media. American history and jurisprudence embrace free speech as a grounding principle of democracy, yet simultaneously subject speech to limitations. Finally, through a comparative exploration of real-world examples, we address the narrow instance when limitations on inciteful and targeted hate speech are appropriate.