Failure of issue is definite or Indefinite. When the precise time for the failure of issue is fixed by the will, as in the case of a devise to Peter, but if he dies without issue living at the time of his death, then to another, this is a failure of issue definite. An indefinite failure of issue is a general failure whenever it may happen, without fixing any time, or a certain and definite period, within which it must happen. 4 Kent 275. An executory devise in fee, with remainder over, to take effect on an indefinite failure of issue is void for remoteness, and hence courts are astute to devise some construction which shall restrain the failure of issue to the term of limitation allowed ; id. 276, n. See Appeal of Bedford, 40 Pa. 18; 2 Redf. Wills 276, n.; En Ventee Sa Meeb; Shelley’s Case, Rule in.
Source: Bouvier’s Law Dictionary & Concise Encyclopedia, 3d revision
“There has been considerable litigation during the past several centuries over the meaning to give to ‘A and his heirs, but if A shall die without issue, to B and his heirs.’ First of all, what does ‘die without issue’ mean? The answer appears simple — you look to the time of A’s death to determine whether or not he has any children or grandchildren. But that is not the way the English courts originally construed this language. The English adopted the so-called ‘indefinite failure of issue’ construction — if at any time in the future A’s line of descent should come to an end, then there was a gift over to B and his heirs. The effect of this was a fee tail in A and a remainder in B. This seems a distortion of the language, and particularly unsuited to American circumstances since the fee tail never found a real home here. Most of our jurisdictions, by judicial decision or statute, adopted the so-called ‘definite failure of issue’ construction — you look to the date of A’s death to determine whether he has issue, and to that time alone. If A has issue at that time, then the gift over to B fails. This seems to be the literal meaning of the words, and it is the only sensible conclusion in a system where the fee tail is virtually a dead letter. The English also struck down the constructional preference for indefinite failure by statute in the nineteenth century.”
Source: Thomas F. Bergin & Paul G. Haskell, Preference to Estates in Land and Future Interests 236-37 (2d ed. 1984).