a small or narrow opening, as in a wall, for looking through, for admitting light and air, or, particularly in a fortification, for the discharge of missiles against an enemy outside. See illus. under battlement.
an opening or aperture.
a means of escape or evasion; a means or opportunity of evading a rule, law, etc.: There are a number of loopholes in the tax laws whereby corporations can save money.
verb (used with object), loopholed, loopholing.
to furnish with loopholes.

1585–95; loop2 + hole

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Based on the Random House Dictionary, © Random House, Inc. 2014.
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World English Dictionary
loophole (ˈluːpˌhəʊl)
1.  an ambiguity, omission, etc, as in a law, by which one can avoid a penalty or responsibility
2.  a small gap or hole in a wall, esp one in a fortified wall
3.  (tr) to provide with loopholes
[C16: from loop² + hole]

Collins English Dictionary - Complete & Unabridged 10th Edition
2009 © William Collins Sons & Co. Ltd. 1979, 1986 © HarperCollins
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Word Origin & History

1464, from M.E. loupe "opening in a wall" (c.1300), perhaps related to M.Du. lupen "to watch, peer;" + hole. Figurative sense of "outlet, means of escape" is from 1663.
Online Etymology Dictionary, © 2010 Douglas Harper
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Example sentences
It was unscrupulous labeling not a loophole in the regulation.
The only possible loophole is when someone claims to have had two legitimate
  emergencies during the semester, both on test days.
Skeptics insist, notwithstanding scientific evidence, that there could always
  be a catch or a loophole.
There's no sense in being a typical blogger, commenting on serious matters by
  trying to find every flaw and loophole in a story.
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