In this study, I have focused on a meaningful portion of Jirmānūs Farḥāt’s (d. 1732) pedagogical production and on his philological method in the fields of naḥw (grammar) and lugha (lexicography/lexicology). In particular, I have analyzed two texts, both authored at the outset of the eighteenth century: the grammar manual Baḥth al-maṭālib wa-ḥathth al-ṭālib (“The Pursuit of the Answers and the Encouragement of the Student”) and the lexicological poem with an ascetic gist al-Muthallathāt al-durriyya (“The Pearly Triplets”). While analyzing these works, I have also discussed how they were used in the seminaries of Mount Lebanon in the eighteenth century and in the Ottoman public schools in the nineteenth century. This study is guided by the questions: What were Farḥāt’s pedagogical aims? How did he re-elaborate the Arabic-Islamic language scholarship in his work? To what extent was his work novel? Was his work influenced by European pedagogical texts on the Arabic language? This study also aims to shed light on the history of the pedagogy of Arabic and its development among Arab Christians in the nineteenth and the early twentieth centuries by discussing the extent of Farḥāt’s impact on the pedagogical approach of the scholars of the time. This study challenges the view that naḥw and lugha were auxiliary to other disciplines. In fact, it explores them in themselves by observing them from within the cultural and scholarly environment in which they were produced and used. Furthermore, this study challenges the concept of ‘imitation’ as taqlīd and inquires whether, in the context of early modern Arabic textual practices, it could be addressed as muʿāraḍa instead, i.e., the reworking of a literary model out of admiration for its author and his writing. Consequently, it aims to show that early modern texts can be observed through the lenses of intertextuality and creativity instead of being considered mere copies. Finally, this study looks at the entanglements between Mount Lebanon (in the Ottoman Levant) and Rome (Europe), and it enquires whether Farḥāt’s pedagogical works have been the product of the local Arabic-Islamic curriculum of the Ottoman madāris and also the result of the Maronites’ link to the Jesuits’ teachings in Rome and through the missions in the Levant. In Chapter Two, I have investigated Farḥāt’s handwritten draft of the grammar manual Baḥth al-maṭālib (Cod.arab. 770), which he wrote in 1707, now preserved in Munich at the Bayerische Staatsbibliothek, and I have compared successive manuscript copies, starting from the abridgement produced a year later, against it. In analyzing Baḥth al-maṭālib, I have explored the text’s purposes, arrangement, content, and the Arabic-Islamic sources it depended on. Moreover, I have also examined Farḥāt’s philological approach, while reflecting at once on his choice to produce a mukhtaṣar and on the use that students made of his book. In Chapter Three, I have investigated the nineteenth-century printed editions of Baḥth al-maṭālib, and I have focused on the shift from textbook only circulating in Mount Lebanon to school manual employed in the public schools of the Ottoman Empire in Syria/Lebanon. In the first part of the Chapter, I have illustrated the engagement of three nineteenth-century scholars with the book, namely Aḥmad Fāris al-Shidyāq (d. 1887), Buṭrus al-Bustānī (d. 1883), and Saʿīd al-Khūrī al-Shartūnī (d. 1912), who produced the most famous and widespread editions of Baḥth al-maṭālib. In the second part, I have examined four nineteenth-century and early twentieth-century Arabic grammar books, authored by Arab Christian scholars, who followed in Farḥāt’s pedagogical footsteps. These books include Nāṣif al-Yāzijī’s (d. 1871) manual Faṣl al-khiṭāb fī uṣūl lughat al-aʿrāb (“The Decisive Speech about the Principles of the Language of the Desert Arabs”), Fāris al-Shidyāq’s Ghunyat al-ṭālib wa-munyat al-rāghib (“The Enrichment of the Student and the Wish of the Seeker”), Rashīd al-Shartūnī’s (d. 1907) – Saʿīd’s brother – Mabādīʾ al-ʿArabiyya fī al-ṣarf wa-l-naḥw (“The Foundations of Arabic Morphology and Grammar”), and the Maronite Antonian monk Yūsuf al-Juʿaytāwī’s (d. 1908?) Kifāyat al-ṭālib wa-bughyat al-rāghib fī ʿilm al-naḥw (“The Sufficient for the Student and the Fulfilment of the Desirous in the Science of Grammar”). By analyzing these texts, I aim to show the impact of Farḥāt’s methodology on nineteenth-and early twentieth-century grammar books. In Chapter Four, the focus shifts from grammar to lexicology. I have translated and the analyzed the ascetic poem al-Muthallathāt al-durriyya, which stylistically draws upon the triplet-model devised by Abū Alī Muḥammad b. al-Mustanīr “Quṭrub” (d. 206/821). By tracing a short history of the engagement of Arab-Muslim scholars with triplet words, I have discussed the concept of muʿāraḍa as creative imitation, and I have reflected on Farḥāt’s engagement with Arabic lexicography. Furthermore, I have underlined that the poem was not only a learning tool for the students but also a place for the author to express his predilection for contemplative life, which suggests the existence of similarities between monastic life and Sufi practices. Finally, I have also touched upon Farḥāt’s self-commentary on his poem. In the conclusions, Chapter Five, I have provided a summary of the results, and I have discussed the implications of this research. I have reflected on what Farḥāt’s Arabic pedagogical program entailed for the Maronite community and its history. Finally, I have suggested further lines of inquiry. With this dissertation, I hope to have uncovered unknown aspects of Farḥāt’s production and offered some useful insight into the Levantine Christians’ engagement with Arabic language and its pedagogy in the eighteenth and in the nineteenth centuries.