Strictly speaking, a form of entail was known before the Norman feudal law had been domesticated in England. The common form was a grant "to the feoffee and the heirs of his body," by which limitation it was sought to prevent 'alienation from the lineage of the first purchaser. These grants were also known as feuda conditionata, because if the donee had no heirs of his body the estate reverted to the donor. This right of reversion was evaded by the interpretation that such a gift was a conditional fee, which enabled the donee, if he had an heir of the body born alive, to alienate the land, and consequently disinherit the issue and defeat the right of the donor. To remedy this the statute De donis conditionalibus was passed, which enacted that in grants to a man and the heirs of his body, the will of the donor according to the form in the deed of gift manifestly expressed, should be from thenceforth observed; so that they to whom the land was given under such condition, should have no power to alienate the land so given, but that it should remain unto the issue of those to whom it was given after their death, or unto the giver or his heirs, if issue fail.
Since the passing of the statute an estate given to a man and the heirs of his body has been known as an estate tail, or an estate in fee tail (feudum talliatum), the word tail being derived from the French tailler, to cut, the inheritance being by the statute cut down and confined to the heirs of the body. The operation of the statute soon produced innumerable evils: "children, it is said, grew disobedient when they knew they could not be set aside ; farmers were deprived of their leases; creditors were defrauded of their debts; innumerable latent entails were produced to deprive purchasers of the land they had fairly bought; treasons also were encouraged, as estates tail were not liable to forfeiture longer than for the tenant's life". On the other hand, by limiting inheritance to the eldest son, the other issue were forced to seek employment elsewhere, thus, it has been argued, preventing the growth of a landed caste. The professions of the church, the army and the law were constantly recruited from the younger sons of landed families, preventing the gap between nobility and the rest. Nevertheless, the power of alienation was reintroduced by the judges in Taltarum's Case (Year Book, 12 Edward IV., 1472) by means of a fictitious suit or recovery which had originally been devised by the regular clergy for evading the statutes of Mortmain. This was abolished by the Fines and Recoveries Act 1833, which provided an alternative means of barring entails.