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Maybe I have chosen the wrong words. I have read about it a couple of months ago. Could look for the article (written in German).
To resell things is legal, that's the main argument of the sellers of these licenses. But in this case is not guaranteed to be "valid".
The licenses are part of a corporate bulk, that didn't get fully used. The problem is... if the company that purchased these licenses had "problems" with Microsoft, and Microsoft does something with that bulk of licenses.... then the private people that have bought these cheap licenses would be affected too and can have problems with an unlicensed Windows after X time working fine.
If Microsoft ever "cancels" such a license bulk, or if the private people then get "reactivated" after that cancellation... is another point.
EDIT: Economically speaking... Probably still worth the try / risk
M.D.V. 
If something has a solution... Why do we have to worry about?. If it has no solution... For what reason do we have to worry about?
Help me to understand what I'm saying, and I'll explain it better to you
Rating helpful answers is nice, but saying thanks can be even nicer.
modified 20-Apr-20 6:39am.
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That is how it goes: The company buys what is named a volume license = a large (sometimes even unlimited) amount of licenses that may or may not be limited in time, for a certain price. The volume licensing service is explicitly stating the company as future owner of these licenses.
The company then uses only part of these, and then sells other license-IDs to a very small amount of money in regards to what such a license normally costs on the market. Here are the problems: Is the company allowed to resell the license that was issued from a deal between the license provider and the company with explicit limitation ? IF yes, is it allowed to resell it to such low a price ? And this is regulated differently in different parts of the world - the globalization makes it even more complicated to handle.
Plus, very few company owners know about this, and it is happening that the IT guys profit from this "un"knowledge by selling the extra licenses as a side remuneration; so when buying such a license, it is hard to tell if you are not profiting of stolen goods (not due to the resell of licenses, but of the stealing from the volume license).
Even if done with the company's consent, it can be a conflict to sell a product for a price largely below the market. If this is really legal, I could create a building company, buy one million MSOffice licenses for my "development team" for $5,000,000 and sell them each for $8 to $10. The selling process is mostly automated (auctions, automatically generated emails with keys after auction completion,...), so limited effort required.
modified 20-Apr-20 7:28am.
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Setting up a company for the purpose of trading the way you say would would likely be in breach of fair-trading regulations, and microsoft could sue parties who did so, but that would have no effect on the validity of any licenses sold.
The only criminals you've mentioned are "IT guys". I've just done a search and found no-one charged with this crime, so we can assume it appears to be a theoretical postulation only (read: "FUD"), and I'm sure that many IT guys who own baseball and/or cricket bats would love to discuss the validity of your accusation.
It doesn't matter whether you own one copy of a book or fifty; you are perfectly entitled to sell them on.
What is almost certainly not legal is the binding of licenses to MAC addresses, but companies that do so also unbind them, when requested, so there haven't been any lawsuits about that, either.
I wanna be a eunuchs developer! Pass me a bread knife!
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You made it right. 
Press F1 for help or google it.
Greetings from Germany
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That's what I always do, even if I am aware of the legal grey zone and the risks - see my other post.
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OEM licenses are great, I bought XP that way years ago. The guy I bought it from had to give me a few codes to try, because they buy blocks but in the end it worked fine.
Young enough to know I can.
Old enough to know I shouldn't.
Stupid enough to do it anyway!
JaxCoder.com
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Is that for a key only, or with a CD or download?
Just curious...at that price, I'd expect a CD/downloaded bits to contain..."a little extra"?
The $339 figure you get from MS itself is for support. They really, really don't want people coming to them directly.
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Here in Germany you pay for an email / paper with a license number... no CD, no Download code or whatsoever.
M.D.V.
If something has a solution... Why do we have to worry about?. If it has no solution... For what reason do we have to worry about?
Help me to understand what I'm saying, and I'll explain it better to you
Rating helpful answers is nice, but saying thanks can be even nicer.
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So where are you expected to get the bits from?
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Online download. Microsoft still offers the Media Creation Tool
A.k.a... you have to search it on your own
M.D.V.
If something has a solution... Why do we have to worry about?. If it has no solution... For what reason do we have to worry about?
Help me to understand what I'm saying, and I'll explain it better to you
Rating helpful answers is nice, but saying thanks can be even nicer.
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Key Only. Rest is up to you though seller has a video on youtube on what to do.
Zen and the art of software maintenance : rm -rf *
Maths is like love : a simple idea but it can get complicated.
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...Lorraine is gone 
I don't think a coat's gonna help me here...
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I wanna know, have you ever seen Lorraine?
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oh yeah - when Lorraine comes, they run and hide their heads!
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PIEBALDconsult wrote: wanna know, have you ever seen Lorraine?
Nope. I guess Lorraine's down in Africa.
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Yeah, it was a sunny day. 
Did you ever see history portrayed as an old man with a wise brow and pulseless heart, weighing all things in the balance of reason?
Is not rather the genius of history like an eternal, imploring maiden, full of fire, with a burning heart and flaming soul, humanly warm and humanly beautiful?
--Zachris Topelius
Training a telescope on one’s own belly button will only reveal lint. You like that? You go right on staring at it. I prefer looking at galaxies.
-- Sarah Hoyt
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Tim Deveaux wrote: I don't think a coat's gonna help me here...
I won't be placing any obstacles in your way.
I wanna be a eunuchs developer! Pass me a bread knife!
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All of the bad feelings have disappeared
Young enough to know I can.
Old enough to know I shouldn't.
Stupid enough to do it anyway!
JaxCoder.com
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Don’t get too comfortable with Carly. One day you will look up and say “ Here comes Lorraine Again”!
If you can't laugh at yourself - ask me and I will do it for you.
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I'm trying to work that into "you can't have a rainbow without a little rain" somehow but keep falling short.
And the attributions I keep finding are for Dolly Parton. Really?
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A man is staying at an old-fashioned pub/inn. Downstairs in the tavern he is drinking before retiring to his room. The innkeeper approaches him and proposes a challenge. He has a magical chicken that will grant him one wish if he can beat her in a trivia contest.
The man is bemused but accepts the challenge, figuring there's no harm in indulging him.
The man brings out the hen from the back room. The innkeeper explains that she only speaks Spanish, but he will translate. The man also speaks Spanish so they decide to have the contest in Spanish.
They begin the trivia battle and the chicken wins decisively. The hen speaks perfectly Spanish and answers every question accurately.
The man is blown away, a little disappointed not to get his wish but deciding that the novelty of a genius talking chicken was worth the time anyway. He tells in the innkeeper about how he didn't anticipate having such an interesting evening.
The innkeeper laughs and says "No one expects the Spanish Inn quiz wish hen".
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You better, and here's yer shoes too.
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The coat check clerk sold his coat to help pay his fine.
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I've never heard that one before. I wish it still hadn't.
Freedom is the freedom to say that two plus two make four. If that is granted, all else follows.
-- 6079 Smith W.
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