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from The American Heritage® Dictionary of the English Language, 4th Edition

  • n. A way of escaping a difficulty, especially an omission or ambiguity in the wording of a contract or law that provides a means of evading compliance.
  • n. A small hole or slit in a wall, especially one through which small arms may be fired.

from Wiktionary, Creative Commons Attribution/Share-Alike License

  • n. A method of escape, especially an ambiguity or exception in a rule that can be exploited in order to avoid its effect.
  • n. A slit in a castle wall. Later: any similar window for shooting a weapon or letting in light.
  • v. To prepare a building for defense by preparing slits or holes through which to fire on attackers

from the GNU version of the Collaborative International Dictionary of English

  • n. A small opening, as in the walls of fortification, or in the bulkhead of a ship, through which small arms or other weapons may be discharged at an enemy.
  • n. A hole or aperture that gives a passage, or the means of escape or evasion.
  • n. An amibiguity or unintended omission in a law, rule, regulation, or contract which allows a party to circumvent the intent of the text and avoid its obligations under certain circumstances. -- used usually in a negative sense; -- distinguished from escape clause in that the latter usually is included to deliberately allow evasion of obligation under certain specified and foreseen circumstances.

from The Century Dictionary and Cyclopedia

  • n. A small aperture, narrow toward the outside and splayed within, in the walls of a fortification or of any similar structure, through which small-arms may be fired at an enemy, or observations may be taken.
  • n. An opening into or out of anything; a hole or aperture that gives a passage or the means of escape: often used figuratively, and especially of an underhand or unfair method of escape or evasion.

from WordNet 3.0 Copyright 2006 by Princeton University. All rights reserved.

  • n. a small hole in a fortified wall; for observation or discharging weapons
  • n. an ambiguity (especially one in the text of a law or contract) that makes it possible to evade a difficulty or obligation


loop2 + hole.
(American Heritage® Dictionary of the English Language, Fourth Edition)
loop +‎ hole (Wiktionary)



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  • Fabulous! Thanks, slumry.

    August 11, 2015

  • from comes this discussion of loophole:
    The narrow, slit-like windows often found in Medieval castles were called loopholes. Loop is a now obsolete word for "window", so a loophole was a "window hole". These narrow windows were used for defense of the castle - it was easy to launch arrows and other projectiles out of the castle through such slits, but awfully difficult to get them in. So it would make sense that this word might come to mean "some means of escape" and then "some technicality that allows one to evade some consequence of a contract".
    However, that's not where today's loophole comes from! Well, at least not directly. Instead, it has been suggested that it comes from Dutch loopgat, the loop part of which comes from loopen "to run" (related to English lope and leap). It was probably influenced by the similar word loophole "window slit", perhaps even by folk etymology of the type we tried to fool you with above.
    Loophole in the "technicality that allows evasion" sense was first used by the poet Andrew Marvell in 1663.

    August 11, 2015

  • Why loop?

    August 11, 2015

  • In castle architecture, a vertical slit for air, light, or shooting (presumably objects) through.

    August 25, 2008

  • It's it great how loophole has so many loops and holes? Somebody had a list for words like this....

    January 20, 2008