This chapter focuses on the ways in which maskilic (Jewish enlightenment) authors reshaped elements of the Hebrew language in order to make it suitable for use as a vehicle of modern European-style literature. Maskilic authors were motivated by the principle that the creation of a Hebrew literary canon based on European-language models was an essential component of the Jews’ Enlightenment. They developed a wide range of new written genres which had not previously existed in Hebrew, including original and translated novels, short stories, novellas, anecdotes, feuilletons, and plays; a flourishing press; popular science (e.g., astronomy, physics, biology, chemistry, zoology), politics, geography, and history; and fiction and nonfiction works for young readers. This large-scale endeavor resulted in the emergence of numerous linguistic innovations. In this chapter we examine several key yet understudied innovative features of maskilic Hebrew: 1) realistic colloquial dialogue, including a) new punctuation norms, b) use of interjections, and c) forms of address; 2) discussions of contemporary scientific and political topics using newly developed Hebrew vocabulary and European loanwords; and 3) prose syntax based on German and Russian stylistic models. These new components of Hebrew paved the way for the later vernacularization of the language in Ottoman Palestine.