The World of Sketchy Windows Key Resellers

I was hoping for a blatant scam: fake Windows keys sold through Reddit rings, Groupon, and half-assed websites.

So I bought what I assumed to be a fake Windows key that would fail the authentication. What better way to prove the scam?

The key fucking worked.

Real Windows 11 Home keys go for about $140. I bought one for $32. Microsoft authenticated the sketchy $32 key.

Maybe I should have tried one of the $9 keys instead.

So I can’t say that these dodgy Windows key resellers are scamming people.

But what I can do is break down all the fucked up shit they’re doing with marketing. Cause it’s dodgy as hell.

Ranking for “Windows Key” in Google via Reddit

Like so many sketchy corners of the internet these days, we begin with a Google search and a Reddit ranking.

Right after a support article on where to find your Windows key on your retail box (if you bought one), we get a Reddit thread on buying a Windows 10 key. Surely this will be legit.

Here’s the post:

I’m confident this is a fake post.

If you go through the post history of that user, you’ll find tons of posts that sound like this from about 2 years ago:

A completely different person.

After going through the user’s history, a few things are clear:

The user is likely from Argentina
English is a second language
All their old posts sound nothing like the Windows 10 key post that’s being used to rank in Google

There was an immediate tone shift on the account about a year ago, the same user posts 3 times about Windows 10 keys:

Then a couple token comments, then the account goes silent. Yeah, not suspicious at all.

This was a real account. It’s no longer a real account. Never trust a Reddit thread that ranks in Google. Even if a post looks real, it’s probably not.

So what do the comments look like in our original Windows 10 key thread?

Yeah, those are 100% fucking fake. That vendafly.com link is a dead giveaway. None of these replies are from real users. It’s probably the same person that published the original post and then followed up with replies from alt accounts. And I wouldn’t be surprised if a moderator of r/desktops was in on it too. That’s the best way to avoid getting the posts and comments deleted.

Both the post and the top comments have so many upvotes that the person that ran this fake marketing stunt also likely paid for Reddit upvoting. There’s a bunch of services that do this.

Let’s recap how a user enters this sketchy marketing funnel.

People are searching for “Windows key” on Google. Most people don’t know how Windows keys work, they just know they need one. They assume Google will help them find one.
The second ranking in Google is a Reddit post. I believe the post is fake. Someone got ahold of a previously real Reddit account and used that account to seed a fake post that would rank in Google.
The unknowing searcher will hit that Reddit thread and see a bunch of comments at the top that all recommend vendafly.com. “Everyone recommends the same site! What luck!”
All the comments and upvotes look fake to me.
With a click, that searcher is now in a sketchy funnel. All promoted by Google and allowed by Reddit.

Is Vendafly a Legit Business?

Depends on how you define legit.

I did some digging into these folks. And everything about their business screams “hey, we’re super duper sketchy!” It’s so bad that I’m still shocked that my Windows key worked.

The Trust Pilot Marketing Push for Vendafly

Across their website, they reference their Trust Pilot reviews heavily. This is right on their homepage:

Are we fuckign serious right now? This website is one of the top 10 computer software stores on the whole goddamn internet? Da fuq?

Surely a third party review site like Trust Pilot can’t get manipulated, right!?

I wish. Trustpilot rankings mean nothing.

To Vendalfy’s credit, they’ve put a ton of effort into jacking up their Trust Pilot rating (which I don’t believe for a second):

No fuckign way that most of those reviews are real. Many of them seem extremely similar and there’s a super consistent drip of reviews since they started on Mar 19, 2024. 550 reviews in just over a year? That’s nuts. There’s a few real reviews but I’d bet that most are fake.

Also, Vendafly hasn’t confirmed any of their company details with Trust Pilot:

Considering Trust Pilot is a pivotal part of their marketing strategy, I find it extremely suspicious that they haven’t taken the time to confirm any of their company details.

Vendafly And Digital Chill Mart Are the Same Company

The same folks behind Vendafly also run Digital Chill Mart. It’s almost an identical website, funnel, and marketing push between both websites.

Some easy proof that connects the companies: Trust Pilot reviews mention the same employees. Here’s one for Vendafly:

And here’s Digital Chill Mart:

Both mention Lamia. Other employees are also mentioned across both Trust Pilot profiles.

I see this as another red flag. Why run both websites that are nearly identical? And both of them are very murky on who’s actually running them.

Against My Better Judgement: Buying a Sketchy Windows Key

Now let’s go do something stupid.

When I was tipped off about this Windows key Reddit thread, my first thought was: “I HAVE to buy that Windows key. This is a terrible idea but I have to do it.”

So I did it.

The purchase funnel is pretty normal to be honest, it’s just a third-rate design. If you go to Vendafly site, you’ll see a batch of keys for sale just like any ecommerce site:

Pretty normal checkout funnel from that point on. And the key arrives instantly after purchase via email.

So I went over to my Windows machine and popped it in:

Then the fucker actually authenticated:

It worked the first time. As of publishing this post, it’s still working.

I Expect My Sketchy Windows Key to Fail At Some Point

When I was in high school, it wasn’t too hard to get your hands on Windows and Office key generators. Just had to sail into rough and choppy seas.

Those keys would work for 6-9 months and then fail once Microsoft caught on. Then you’d trial and error your way through some new key generators, eventually get an authentication, then wait until the next failure.

I’m expecting the same process here. I’ll add an update if the key ends up failing. If I haven’t updated this section, you can assume that my key is still working.

The Most Likely Outcome If You Buy a Windows Key from Vendafly

If you make the same dumb decision that I did and buy a Windows key (or any license) from Vendafly, here’s what I’d expect to happen:

There is a chance that the authentication will go through and you’ll get a windows license on the cheap. I’d expect it to fail in the future though.
There’s a good chance that the key fails. It sounds like the support emails are all dead, you’ll have to use their chat bot. Lots of reports from people that they get successful keys on the 2nd or 3rd try.
This is definitely a moral gray area. The vendors are not supposed to have these keys, the odds they bought them directly from Microsoft is extremely low. Some websites might give you a real key, others might be a straight scam.

The Worst Part: Google Makes Money Off This Gray-Market

Not only does Google fuel this industry by not vetting the Reddit threads that it chooses to rank at the top of search results, they make money directly from companies selling these sketchy Windows keys. Look at all the ads at the top of the search results:

These ads have been running for years.

And yes, that Groupon link is part of this industry. A number of companies in this space have figured out they can open Groupon profiles and sell stuff at a discount. Perfect for the gray-market Windows keys.

Conversions go up because Groupon feels like a trustworthy brand even though it sold its soul years ago.
Groupon doesn’t ask too many questions on how these companies get their keys in the first place.
Groupon gets paid, Google gets paid, and the sketchy reseller gets paid.

Where Do Windows Key Resellers Get Their Keys?

I’ve found a few theories on how all this works here and here:

There are non-retail ways to get bulk keys from Microsoft like enterprise deals for a university. If those keys get resold when they shouldn’t, they could end up on these websites.
Some folks have claimed there are credit card fraudsters that will quickly buy a bunch of keys using stolen credit cards, then quickly resell them.
They could have a keygen that they’re using to generate keys themselves.

Regardless, these folks aren’t aren’t getting the Windows keys from Microsoft. And I’d bet Mircrosoft wouldn’t be happy if they discovered who was selling these keys to the resellers. That’s why the keys are so cheap.

I Do Not Recommend Buying One of These Discount Windows Keys From Any Website

Even if my reseller happened to sell me a real key (which I still doubt that it’s 100% legit), there’s so many sketchy things about these websites that I’d be shocked if there isn’t a scam of some kind. Ways that I’d expect to get scammed:

The windows key fails at some point
Some of the keys fail predictably and they make money when some users don’t contact their support to get a new key.
I had to create an account and set a password on the site I purchased from. If people use the same password as their email, it would be very easy to get into their inbox without two factor set up. That’s game over.
I wouldn’t be surprised if I got fraudulent credit card charges at some point.

This is a sketchy corner of the internet, stay the fuck away.

Go buy your Windows key from a major retailer. For Amazon, I can’t find a normal Windows 11 Home license on Amazon, only the OEM version (affiliate link). Newegg (no affiliate) and Microsoft (no affiliate) have you covered though.

Do not put your credit card into one of these reseller websites.

What’s the Best Way to Get a Windows Key Discount?

There is one 100% legit way to get a discount on a Windows key: buy an OEM version of Windows (affiliate link) for about $110.

I’ve been doing this since high school.

It’s not nearly as good of a discount as it used to be, I seem to remember it being like 40% off retail. These days, it’s about 20% off the retail version.

You get a 100% legit version of Windows with only these downsides:

No Windows support from Microsoft. But who cares about that?
You can’t transfer the key to another device. Normal retail keys get tied to your Microsoft account and Microsoft is pretty generous about letting you transfer keys between devices. OEM versions don’t get this benefit. It’s one and done on the device.
Comes on a DVD instead of a USB. I can’t remember the last time I had a DVD drive so you’ll need to manage the install yourself instead of just plugging in a USB.

These days, I just buy the retail license so I can easily transfer keys between devices whenever I rebuild my gaming rig. The OEM isn’t worth the $30 discount to me.

Do ChatGPT or Perplexity Succumb to the Same Sketchy Marketing as Google?

ChatGPT and Perplexity both do better than Google. But they each make their own mistakes.

I asked ChatGPT for “how do I get a windows key?” and got the standard info on where to buy retail. I also got this:

Is this better than Google? Yes. But it has some flaws:

ChatGPT calls these gray market keys “OEM keys”. That makes them sound way more legit than they are. OEM keys are a particular type of windows license that anyone can buy. These sites are not selling the same “OEM” keys that you’d get from Amazon.
“Some are gray-market”…. that’s pretty optimistic. All of them are gray market. And these companies are not operating with transparency. They know they’re not supposed to have these keys.

ChatGPT does better than any other search engine I tested by giving a warning that these keys might stop working. That is, by far, the most common risk for these types of licenses.

Perplexity gives a similar answer:

There is a few things that Perplexity fucks up:

In the answer above, Perplexity states that Digital Chill Mark and Vendafly (both operated by the same people) are reliable sources. It then references one of the Reddit threads that I believe is fake. Perplexity is falling for the same bullshit that Google is.
I’ve asked Perplexity a few variants on how to buy Windows licenses and it will say that Trust Pilot is trustworthy and a good way to find the legitimate sellers for Windows keys. It most assuredly is not.
In its warning about OEM keys, Perplexity makes it sound like these are normal OEM keys. They’re not. They’re likely to fail once Microsoft discovers that they’ve been sold illegitimately. Normal OEM keys are totally different.

I do appreciate that Perplexity has some warnings about buying these cheap Windows licenses, so that’s better than Google. The warnings aren’t as good as ChatGPT though since there’s no mention of how these keys can fail.

What about Google AI Mode?

Here’s Google’s AI Mode:

Not sure what it means by “Microsoft only retains records of keys bought from their online store”. That’s not true. Microsoft absolutely keeps track of all keys it sells.

As for the rest, it’s not technically wrong. But goddamn does it miss a lot. What about OEM keys? What about this sketchy gray market that people will be stumbling into? What about other retailers other than Microsoft? Like, I dunno, a tiny little retailer like Amazon?

It’s bland, superficial, and the lowest quality AI answer in my opinion.

To be fair, there is one warning below where I cut off the screenshot that says “Buying from authorized retailers is recommended to ensure you obtain a genuine product key.” Yeah, no shit.

How I Rank Platforms For Protecting Users from the Sketchy Windows Key Market

Here are my rankings on how well a few search engines do with the Windows key market:

Ranking	Search Engine	Level of Trust	Warnings
The winner	ChatGPT	Gets duped the least. One major factual error.	The best warning of the bunch.
Second place	Perplexity	Does reference fake reviews and Reddit threads without realizing they’re fake. Some factual errors.	Some warnings, could have been better.
Third place	Google AI Mode	So bland there’s nothing to trust.	One minor warning.
Fourth place	Google	Links directly to sketchy Reddit threads.	None, good luck!

Will the Windows License Market Survive the Migration to AI Search

Yup. These sites are doing just fine in the AI tools. I see many of the key players get named by brand in both ChatGPT and Perplexity.

They’re actually a perfect case study on how to survive the transition:

Get your Trust Pilot and similar review sites (Trust Radius, G2, etc) reviews up. I should do a whole post on how to buy these reviews.
Seed Reddit with plenty of threads with people talking about your product in a positive light. Either do it authentically or have a connection with the moderator team to make sure your post isn’t deleted. Also focus on subreddits that Google “trusts” for search rankings.
Links don’t matter. Vendafly.com only has 64 backlinks and they’re extremely low quality. The Domain Rating is 17. So don’t worry about paying for backlinks, just go pay for reviews instead.

That’s the playbook: ditch link building, get your reviews up, and seed Reddit.

Are the AI Search Tools Doing Enough for This Gray-Market?

I don’t think so.

While AI does give some warnings, the warnings are insufficient in my opinion. They’re not 100% wrong, but key context is missing:

The gray market keys are labeled as OEM which sounds way more legitimate than they are. Also, we’re not sure where the keys came from.
The biggest warning of all (your key will likely fail) is barely mentioned at all. This needs to be front and center.
Perplexity especially has a problem of making it seem like these keys can be legitimate if you find the right retailer. That’s not true, none of these websites are trustworthy.

Both ChatGPT and Perplexity should be doing more here. They’re better than Google but that’s a very low bar at the moment.