See also: loop hole


A loophole.



From Middle English loupe (opening in a wall) +‎ hole, from a Germanic source. Compare Medieval Latin loupa, lobia and Middle Dutch lupen (to watch).[1]





loophole (plural loopholes)

  1. (historical) A slit in a castle wall; today, any similar window for shooting a ranged weapon or letting in light. Also written loop hole.
    • 1719 May 6 (Gregorian calendar), [Daniel Defoe], The Life and Strange Surprizing Adventures of Robinson Crusoe, [], London: [] W[illiam] Taylor [], →OCLC:
      [] and having a fair loophole, as it were, from a broken hole in the tree, he took a sure aim, without being seen, waiting till they were within about thirty yards of the tree, so that he could not miss.
    • 1809, Maria Edgeworth, The Absentee:
      There was a loophole in this wall, to let the light in, just at the height of a person's head, who was sitting near the chimney.
    • 1949, George Orwell, Nineteen Eighty-Four, page 25:
      The sun had shifted round, and the myriad windows of the Ministry of Truth, with the light no longer shining on them, looked grim as the loopholes of a fortress.
  2. (figurative) A method of escape, especially an ambiguity or exception in a rule or law that can be exploited in order to avoid its effect.
    • 1838, Charles Dickens, chapter 49, in Oliver Twist, page 236:
      Coupling the poor girl's intelligence with my previous knowledge, and the result of our good friend's inquiries on the spot, I left him no loophole of escape, and laid bare the whole villany which by these lights became plain as day.
    • 2002, Marc Lawrence, Two Weeks Notice (motion picture):
      You have a contract that says you will work until Island Towers is finalized, which I interpret as completion of construction, or I can stop you working elsewhere. And there's no loopholes, because you drafted it and you're the best.
    • 2013 February 9, Barack Obama, The Support They Need:
      They would rather ask more from the vast majority of Americans and put our recovery at risk than close even a single tax loophole that benefits the wealthy.

Derived terms






loophole (third-person singular simple present loopholes, present participle loopholing, simple past and past participle loopholed)

  1. (military, transitive) To prepare a building for defense by preparing slits or holes through which to fire on attackers
    • 1896, Arthur Conan Doyle, The Exploits Of Brigadier Gerard[1]:
      The lower windows were barricaded, and the whole building loopholed for musketry fire.
    • 1907, A. E. W. Mason, The Broken Road[2]:
      The doors were barricaded, the shutters closed upon the windows and loopholed, and provisions were brought in from the outhouses.
    • 1915, W. H. L. Watson, Adventures of a Despatch Rider[3]:
      The Germans were loopholing it for defence.
  2. (transitive) To exploit (a law, etc.) by means of loopholes.
    • 1988, Macabee Dean, The Ashmadai Solution: A Surrealistic Extrapolation of a Gentle Genocide:
      Abroad they had developed loopholing the law into an art; in Israel they jettisoned loopholing for ignoring the law wherever possible. Obeying laws was for naive fools.
    • 2005, Deborah Rhode, David Luban, Legal Ethics Stories:
      De-moralizing the subject can be, quite simply, demoralizing, as stirring statements of ideals turn into persnickety rules with exceptions crying out to be loopholed.


  • loophole”, in OneLook Dictionary Search.
  1. ^ Douglas Harper (2001–2024) “loophole”, in Online Etymology Dictionary.

Further reading