This article examines the language and diplomatics of a single Medieval Hebrew letter by one of the leading letter-writers of the Cairo Genizah, Solomon b. Judah, Gaon of the Jerusalem Academy in the eleventh century. The letter, composed and written by Solomon himself, is addressed to the head of the rival Babylonian faction in Egypt, Sahlān b. Abraham, with whom he enjoyed an often fraught professional relationship. It deals with a number of matters, including the transfer of charitable funds from North Africa to the poor of Jerusalem and the gaon’s opinion of popular biblical exegesis. Solomon b. Judah is one of the most elegant Hebrew stylists to emerge from the documentary corpus of the Cairo Geniza, and his letters provide an important window on the Palestinian gaonate and its relations with Egypt in the second quarter of the eleventh century.