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...and stick almost exclusively to it?

According to Collins Dictionary:

A loophole in the law is a small mistake which allows people to do something that would otherwise be illegal.

The Grammarist notes that:

Interestingly, the word loophole goes back to the sixteenth century and refers to an architectural feature. In castles of the time, narrow slits were built into the walls where archers could shoot at attackers. These narrow slits were known as loopholes, most probably derived from the Dutch word lûpen meaning to watch.

The term loophole came into use in the seventeenth century in a figurative sense to mean a small opening or a outlet of escape.

How and when did loophole become associated with law?

How old is the expression Every law has its loophole?

  • You'd be hard pressed (hah) to fit out of the castle variety. – marcellothearcane Sep 14 at 18:45
  • @marcellothearcane - yes, but did it refer to the law at that time? – user067531 Sep 14 at 18:47
  • Probably not, but we can set the earliest limit to that. I assume previous uses were literal, so it wouldn't have the law meaning. – marcellothearcane Sep 14 at 18:51
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    The German variant is Schlupf-Loch, apparently akin to schlüpfen, cp to slip through the cracks; Also cp Schlüpfer "slip, briefs", hereinschlüpfen "to slide into [clothes]", aus dem Ei schlüpfen "to hatch" (to peek from the egg?). A meaning "to look" is not connected to the word, as far as I know, that would rather be Luke "a hatch", Luke(n) "lid(s)/slit(s), the eyes, aperture". The Latin etymology of escape is not yet solved, if I remember correctly, it could relate to cape, recibrocal to "unveil, lift the curtain". Ger lupfen, lüften comes to mind. Cp. shop-lifter. – vectory Sep 16 at 18:11
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    More interesting perhaps, Ger Unterschlupf is a fox hole, an animal's burrow or a fugitives hide-out. I'd venture a guess that it related to sleep originally, but I can't be sure. Comparing en.wiktionary.org/wiki/loophole and en.wiktionary.org/wiki/loupe#French the idea must have been telescoping using drops of molten sand. Also, in this view escape might be explained by -scope (which is unsatisfactorily explained as metathesis from spec-, spectacles etc.) The loophole might be a case of syncretism, in the end. – vectory Sep 16 at 19:10
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From WorldWideWords

  • Q From Will Thomas: Where do we get loophole from?

  • Around the middle of the following century loophole began to be used figuratively for a means of escape and by 1700 could have our modern sense of an ambiguity or inadequacy in rules or laws that allows somebody to evade their provisions.

A loophole is an accidental technicality or unclear section of a written legal document that allows someone to avoid following a rule or fulfilling an contractural obligation. If you've discovered a way to get out of paying taxes on money you made last year, you've found a loophole. My sense is the legal sense occurred on or about the time referenced in the World Wide Words citation.

  • In my pessimistic view of the law, a loophole is an underhanded, veiled exception to the law, that is purposefully built-in. It's an exploit of a loophole if exploited, obviously. – vectory Sep 16 at 18:34

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