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By the Cambridge Dictionary

  • To ​legally ​forbid or ​stop something by ​order of a ​court

  • Enjoin also ​means to ​order or ​strongly ​encourage someone to do something

By the Oxford Dictionary

  • Instruct or urge (someone) to do something
  • Law Prohibit someone from performing by issuing an injunction

So basically, "He is enjoined to stop" can mean either way.

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    From the definitions I've found, including the ones you cited, the prohibition or "discourage" meaning is particular to the US and almost exclusively the domain of law. In British English it only seems to mean "to ​tell someone to do something or to ​behave in a ​particular way". – John Clifford Mar 15 '16 at 21:06
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    Related. – John Clifford Mar 15 '16 at 21:11
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    The legal meaning (at least in Britain) takes a different preposition: he is enjoined from stopping. – TimLymington Mar 15 '16 at 21:16
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    @TimLymington: "Enjoined from" is the standard legal wording in the United States as well—which is not at all surprising considering where the vast majority of U.S. legal terminology originated. – Sven Yargs Mar 15 '16 at 23:11
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    Note that sanction similarly has meanings which are almost opposite: to permit something, and to take action to prevent it. The reason is approximately the same: the origin is the judgment or rule, which could be to permit or to forbid. – Colin Fine Oct 10 '16 at 19:21
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Enjoin: : the common usage is from the old French "enjoindre", impose:

  • [often passive] enjoin somebody to do something enjoin something (formal) to order or strongly advise someone to do something; to say that a particular action or quality is necessary.

The other meaning is only of legal usage and is related to an injunction:

  • To direct, require, command, or admonish.

  • Enjoin connotes a degree of urgency, as when a court enjoins one party in a lawsuit by ordering the person to do, or refrain from doing, something to prevent permanent loss to the other party or parties. This type of order is known as an Injunction.

  • enjoin somebody from doing something (law) to legally prevent someone from doing something, for example with an injunction (= official order)

Enjoin (v.): etymology:.

  • c. 1200, engoinen, "to prescribe, impose" (penance, etc.), from stem of Old French enjoindre (12c.) "impose (on), inflict; subject to; assign (to)," from Latin iniungere "to join, fasten, attach;" figuratively "to inflict, to attack, impose," from in- "on" (see in- (2)) + iungere "to join" (see jugular).
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I do not have a well-documented answer, so please take careful note that this is purely speculative.

The etymology of the first definition of enjoin, where you order someone to do something, is fairly straightforward and well-documented.

http://www.etymonline.com/index.php?term=enjoin

c. 1200, engoinen, "to prescribe, impose" (penance, etc.), from stem of Old French enjoindre (12c.) "impose (on), inflict; subject to; assign (to)," from Latin iniungere "to join, fasten, attach;" figuratively "to inflict, to attack, impose," from in- "on" (see in- (2)) + iungere "to join"

So the question is, how did it also become used to mean "to prohibit"?

Well, as noted Merriam Webster and other dictionaries, this meaning primarily refers to court orders. In this sense, "enjoin" and "injunction" are similar-- the courts enjoin you to do something or to refrain from something by issuing an injunction, and both words share the same root.

It is really just a game of semantics to determine whether an injunction is an order to do something or an order not to do something. For example, if a judge orders you to immediately stop using a trademarked logo, is he ordering you to stop doing something, or to start doing something? You'll have to immediately take action to cover/hide the logo from any storefronts or products you sell, alter your web page design, and so on.

Injunctions are very often orders to "not do" something, so it makes sense that it would pick up this connotation. If someone says "I got an injunction" it tends to conjure up the idea that they got a legal order for you to stop doing something immediately.

And any time an injunction is issued, you've been enjoined. Enjoined to do what? Well, very often, to stop doing what you're doing.

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    Hi Dr.Queso, welcome to EL&U! We tend to discourage speculative answers here as the whole point of the site is to build a database of definitive, well-answered questions, but you've provided links to back up your speculation and explained your viewpoint well enough that I think it's an acceptable and helpful answer, so I don't think any further action is needed on your first post. - From Review – John Clifford Mar 15 '16 at 21:37
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As one comment points out (eventually -- you actually have to follow the link and read), enjoin is an example of a contronym. To quote Kimberly Joki in Grammarly:

A contronym, often referred to as a Janus word or auto-antonym, is a word that evokes contradictory or reverse meanings depending on the context. Specifically, a contronym is a word with a homonym (another word with the same spelling but different meaning) that is also an antonym (a word with the opposite meaning).

The article lists 10 verbs that, like enjoin, are contronyms.

  • It's also a verb, but saying that doesn't answer the question either. The other answers address the history leading to the contronymic usages. – Edwin Ashworth Mar 15 '16 at 22:29
  • @EdwinAshworth Q: How does the word “enjoin” have two opposite meanings? A: It's a contronym. – Gnawme Mar 15 '16 at 22:47
  • Let's see if OP rejects the edit. If it is really just the question 'What are words that are their own antonyms (or homonyms of their own antonyms) called?', it's a multi-duplicate. – Edwin Ashworth Mar 15 '16 at 22:54

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