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An entail (or 'fee tail') is an obsolete form of Freehold estate; it would be granted out of an estate by the Fee simple owner, and would subsist for the duration of the lineage of the grantee. In the event that the lineage came to an end, there was usually a Reversion to the fee simple owner.
In the mediaeval and early modern periods it was quite common for a landed estate to be granted in entail. For the owner of the entailed estate, this meant that he could look forward to his descendants being masters of the estate for the forseeable future. The problem was that it was difficult to sell any part of the estate, because of the principle of Nemo dat quod non habet. That is, the owner of the entail could not give a better title than he himself had, and his title expired on the end of his lineage. This was not appealing for prospective buyers, who were not prepared to take the risk of buying a title that might evaporate without warning. Various complex and rather devious methods were devised to allow entailed estates to be bought and sold, and it eventually became possible for the owner of an entail In possession to dispose of it as if he were the Fee simple owner, barring the claims of any Remainderman. This was good for the entail onwer if he wanted to sell, and for property trading in general, but it prevented the entail owner from ensuring that his own descendants did not sell the land out of the family. The solution to this was the process of 'successive resettlement'. Assume that the 'master' of the estate has a life estate In possession, and his eldest son an entail In remainder. When the son came of age his entail was converted ('resettled') to a life estate, and the entail resettled on his own eldest son (the grandson of the owner of the life estate). Then, when the grandson came of age, his entail itself would be converted into a life interest, and a new entail granted. And so on. The object of this exercise was to prevent the entail in remainder ever coming into possession, and thus prevent it being sold away.