Historical sociopragmatics studies the social dimension of language use from a historical perspective. Like historical pragmatics in general, it must rely on written data (except for the very recent past), which poses some specific analytical challenges. In this contribution, we show how approaches to these challenges have developed in recent years. The research focus in historical sociopragmatics has followed the trend in sociopragmatics, where the earlier focus on a mapping between specific linguistic forms and specific pragmatic functions is increasingly extended to a wider consideration of the discursive nature of pragmatic entities whose function only emerges in the interaction between conversational partners. We illustrate such a discursive approach with an analysis of a sequence of letters from the Breadalbane Collection, 1548--83, in which leading members of a Scottish Highland clan negotiate their relationships, their respective roles and the wider impact of events that led to growing tensions between them.