loophole

From Middle English loupe (“opening in a wall”).

• IPA^(key): /ˈluːphəʊl/
• Hyphenation: loop‧hole

loophole (plural loopholes)

1. (historical) A slit in a castle wall; today, any similar window for shooting a ranged weapon or letting in light.
   • 1719, Daniel Defoe, Robinson Crusoe:

     ... 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. A method of escape, especially an ambiguity or exception in a rule or law that can be exploited in order to avoid its effect.
   • 1839, Charles Dickens, Oliver Twist:

     […] I left him no loophole of escape, and laid bare the whole villainy which by these lights became plain as day.

   • 2002, Two Weeks Notice (movie):

     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.

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:

     The lower windows were barricaded, and the whole building loopholed for musketry fire.

   • 1907, A. E. W. Mason, The Broken Road‎:

     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:

     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.