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This paper presents a case study of the fifty earliest English wills in the Court of Probate, London, with a view to contributing towards highlighting the historical development of this legal genre. By analysing these documents from a pragmatic perspective and setting them in a diachronic framework, I show how the realisation of the act of bequeathing is highly dependent on the socio-cultural context of production and use. Late medieval wills are utterly different from Anglo-Saxon ones in that they are the product of a relatively literate culture in which drafters followed the format of Latin testaments; in this sense late medieval wills are similar to modern ones because they conform to the model of autonomous, formal text. However, they do not fulfil all the felicity conditions necessary to achieve their full constitutive potential as the authority validating these documents remains rooted in religious practices rather than in legal enforcement. This paper offers evidence in favour of the view that a proper pragmatic analysis of medieval documents can only be achieved by taking the historical context into account.