This article highlights challenges involved in understanding and interpreting Byzantine epistolary literature, and suggests that we pay closer attention to the transmission of letters and its hermeneutic ramifications. The letters penned by the late Byzantine court official Nikephoros Choumnos are a case in point. The author assembled, revised and arranged his letters, which were originally composed and dispatched mostly for pragmatic purposes (e.g., letters of request). By embedding these missives into the framework of a collection, he created an autobiographical narrative that was to promote and perpetuate his multi-faceted persona.