The Slavonic letters dispatched by the voivodes of Wallachia to Brașov, where they remain preserved to this day, constitute a major and invaluable source for the fifteenth-century history of Wallachia. In this article, our primary objective is to readdress the undated Slavonic epistolary corpus attributed to Basarab the Elder, who ruled Wallachia with several interruptions between 1473 and 1477. These epistles were addressed by the Wallachian voivode to the Saxon town of Brașov, while the answers of the Saxon authorities to the Wallachian lord did not generally survive. A diligent analysis of the clerks’ handwriting habits alongside a comparative investigation with other types of documentary evidence, such as charters, might not only suggest new reasoned dates for these Slavonic letters, but also could enlarge other research horizons, such as the Romanian-Ottoman relations, the history of audiences and of medieval political discourse, the political thought of the Wallachian lords, the careers of the scribes working in the chancellery, or the functional dynamics of the princely chancellery. Our essay aims to revisit this epistolary corpus through several analytical methods highlighting the usefulness and the potential of such approaches for future research.