This article investigates the transmission of Greek monastic literature into Arabic through a Syriac intermediary, with a focus on Palestinian hagiography. It highlights the translation of The Martyrdom of the Monks of Sinai and Raithu as the earliest known instance of a Greek Christian text rendered into Arabic, which relies heavily on an existing Syriac version. The article presents newly discovered examples from the manuscript collections of St Catherine Monastery, Sinai, illustrating a consistent practice of translations through Syriac in the monastic milieux of Palestine and Sinai (e.g. the Life of Martinianos, the Narrations of Anastasios, etc.). By examining linguistic, philological, and cultural aspects, the study identifies patterns of adaptation, including stylistic and doctrinal modifications, and traces the socio-historical dynamics of these trilingual monastic networks between the eighth and tenth centuries.