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 for loopholes
However, several western companies remain due to loopholes in the sanctions.
Even though chintz was outlawed, there were loopholes in the legislation.
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