Noun

1. A method of escape, especially an ambiguity or exception in a rule 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.

2. A slit in a castle wall. Later: any similar window for shooting a 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.

Verb

1. To prepare a building for defense by preparing slits or holes through which to fire on attackers
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