This chapter analyses two important questions - a) whether typefaces are copyrightable; and b) whether typefaces ought to be copyrightable. To answer the first question, the chapter uses the doctrinal method in research and examines in detail the statutory provisions and important case-laws in three important common law jurisdictions – India, the United Kingdom, and the United States of America. Through this approach, the chapter illustrates the diversity in legal approaches in this important area. The extant international legal regime is also examined for better understanding of the current international legal requirements with regard to providing copyright protection for fonts. The chapter shows that the Berne Convention and the TRIPS Agreement do not mandate copyright protection for typefaces. However, the Vienna Agreement on the Protection of Typefaces provides protection for typefaces. But the Vienna Agreement is neither signed nor ratified by most of the countries including India and the United States. As far as the desirability of copyright protection is concerned, the chapter argues that the “welfare theory” may not extend much support for granting copyright protection for typefaces. The chapter illustrates that in a digital world typefaces may fall under the “negative spaces” of IP and therefore, it merits little IP protection. The chapter calls for more evidence-based discussions and policy debates with regard to copyrightability of typefaces.