This study is devoted to a corpus of Old Russian letters, written on pieces of birchbark. These unique texts from Novgorod and surroundings give us an exceptional impression of everyday life in medieval Russian society. In this study, the birchbark letters are addressed from a pragmatic angle. Linguistic parameters are identified that shed light on the degree to which literacy had gained ground in communicative processes. It is demonstrated that the birchbark letters occupy an intermediate position between orality and literacy. On the one hand, oral habits of communication persisted, as reflected in how the birchbark letters are phrased; on the other hand, literate modes of expression emerged, as seen in the development of normative conventions and literate formulae.