S. F. C. Milsom has lamented how little is known about entail from the fourteenth to the seventeenth centuries. As a partial remedy, his chapter studies grants in fee tail made in the fourteenth and fifteenth centuries. One's first question might well be how frequently was land granted in fee tail. Getting a sense of the frequency of entails is important to forming a picture of overall conveyancing practice, but more important, and more accessible, is getting a sense of the situations that led to the entailing of land. It is a mistake to speak of entails as if they were all of the same type – there were different types of grants in fee tail. The aim is to organize the plethora of conveyances into the main types of entail and the main types of situation in which the parties to a conveyance created an entail.

Perhaps the most frequent use of entails in the fourteenth century was in marriage settlements in which the groom or his father settled land on the groom and bride in joint fee tail, known as jointure. The first part of this chapter explores the change in marriage settlement from a grant of land in maritagium from the bride's family to a payment of a marriage portion in money in exchange for jointure.