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Software on EBay is often deeply discounted and very lucrative. The problem is that those deep discounts sometimes indicate issues to be wary of.

I'd like to purchase another legal copy of Windows XP at a discount. Looking at EBay seems a good idea but how do I know if they are actual Genuine ones? Do I just have to take their word for it?

My question it safe to purchase via Ebay and would you recommend it or not?

It is possible to safely purchase software on EBay. I've done it.

It's also possible to end up with unusable or illegal software, or simply get scammed out of your money.

In exchange for the money you're saving, you need to invest a little time.

The key to successful purchasing on EBay is, in my opinion, spending time carefully reading and understanding the description of the product you are considering purchasing, and carefully reading and understanding the feedback left for the seller you're considering purchasing from.

I did a quick search for "Windows XP" on EBay for this article.

"The key to successful purchasing on EBay is, in my opinion, spending time carefully reading and understanding ..."

All the versions I found were "OEM", meaning that they were originally intended to be sold with a new computer by a manufacturer such as Dell, HP or others. In fact, if you look at the photos of the Windows XP product, you can see that they're shrink-wrapped envelopes that look very similar to the exact same envelops that come with many OEM machines. If the operating system is pre-installed, many people take the shrink wrapped media and sell them on EBay.

I would avoid OEM versions of Windows on EBay for several reasons:

  • The seller is likely in violation of the operating system license, as the OEM disks are for sale with a new computer only, and may only be installed on that one computer. Some vendors try to get around this restriction by including some piece of hardware with your purchase that may or may even not be working or useful. (I was surprised at how blatant this was.) Thereby they've not sold Windows XP alone, but rather "with non-peripheral hardware" which they believe complies with the rules.

  • If these are in fact OEM disks from pre-installed systems, the product key is, presumably, already in use on those systems. You run the real risk of not being able to activate Windows once you install it, as the activation process checks.

  • The OEM version might have differences and/or customizations specifically for the vendor it was originally intended for. It may not work completely on your hardware.

While it's conceivable that some of the OEM versions of Windows XP might be legitimate, the reselling of OEM versions is just too risky for my blood. I would avoid it, period.

Make sure you read the product descriptions carefully. Make sure you know exactly what it is you're purchasing. Unlike a standard retailer, you often have little recourse if the product isn't what you expected. Read the shipping and return policies as well and make absolutely certain that they're to your liking.

And if they seem to be playing games (like shipping unnecessary hardware), to be dancing around some rules, walk away.

Which leads us nicely into feedback.

Almost all feedback on EBay seems to be positive, which in my mind negates some of its value - it's hard to believe that every seller, or every transaction is perfect. That being said, there are a few things to watch for in evaluating the feedback logged against a seller you're considering doing business with:

  • Make sure that you're looking at "Feedback as a seller". The total feedback score appears to include both selling and buying transactions, so it's easy to get what looks to be a stellar reputation simply buying things. One of the Windows XP sellers I located had lots of positive feedback, but none as having sold anything. That makes this person look good, but tells you nothing about how he behaves when selling.

  • Make sure that the feedback is recent, and that there's enough of it. Several hundred items of sales feedback is typically good, but it's concerning when they were all last year, and only a few or infrequent sales occurred within the last 3 months.

  • Make sure that the seller's been around a while. An account created last week hasn't had enough time to build the positive reputation you want in order to feel comfortable doing business.

  • Watch for feedback stuffing. A series of feedback entries that appear identical, or are all from the same buyer should be taken skeptically.

I'm certain that there are great deals out on EBay. I know that many people have made a lot of money there, and have purchased valuable, legitimate items at substantial discounts.

Particularly when it comes to software, however, I think it's important to be extra cautious because we know that there are several ways that the system can be abused.

Yes, I've purchased software on EBay - exactly twice, and specifically to purchase versions of software that were simply no longer available any other way. I much prefer to pay perhaps a little bit more to do business with traditional, reputable retailers like Amazon, Fry's, Newegg and others, with whom I have direct and repeatedly positive experience.

I want to know what I'm getting, and know who I'm getting it from.

Article C3892 - October 16, 2009 « »

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Leo Leo A. Notenboom has been playing with computers since he was required to take a programming class in 1976. An 18 year career as a programmer at Microsoft soon followed. After "retiring" in 2001, Leo started Ask Leo! in 2003 as a place for answers to common computer and technical questions. More about Leo.

Not what you needed?

Jon Schweitzer
October 20, 2009 6:12 AM

Continuing with what Leo stated, you may also be protected by EBay/PayPal. If you do all of the pre-sale research Leo suggested, make your purchase and still have an issue, you still have another option... EBay/PayPal have a counterfeit department which specializes is helping you get justice when wrongly sold an illegal item. I have bought hundreds of items on EBay with several being software (including a Windows XP OEM set). I have gotten quite good at knowing how EBay works and will continue buying and selling there.

Remember, do your research on the product/description and on their feedback. If you are still pleased with the seller after that, you should buy.

Also, a few of the sellers with tons of feedback are big stores themselves. With huge warehouses filled with stock.

Hope this has helped in your future EBay endeavors.


October 20, 2009 6:31 AM

A word about feedback... you may want to cross-check the other buyers' feedback as well. Some eBayers have deals with each other to cross-post great feedback (as buyers) in order to fluff up their ratings. If you see multiple feedback from a buyer, go read their feedback and see if the seller has posted feedback as a buyer, too.

October 20, 2009 9:02 PM

Just so you know, Ebay and PayPal do NOT cover your loses from software sales, as they are classified as an intagiable good

Charles Tilley
October 20, 2009 11:39 PM

Pookey, you're wrong. I got burned in August for counterfeit XP Pro SP3 disc. As mentioned above, the item came with a memory chip, but I wasn't warned about the validation deal upon updating. I got this "nag" in the right corner of my laptop screen that I may be a victim of piracy or counterfeiting. After I notified eBay, they tried to get the man to refund my money, but he fled town. His friend that he was living with said he went back to Mexico. eBay promptly refunded me my money and told me never to worry, they have a strong counterfeit policy. They do not tolerate it, and if reported, the customer will be refunded. Just remember, if the deal sounds too good to be true, it usually is. I paid $83 for a $250-$275 item. I'm a proud member of eBay and I'll vouch that there are many fantastic deals on their site, just be careful about software. I've bought many Linux and Microsoft products on their site with only one bad deal, and they promptly refunded me.

build a niche store
January 28, 2010 12:24 AM

your blog is really nice and use full for me...thanks

February 11, 2010 5:30 PM

I purchased a number of Microsoft Office 2003 on EBay and when I went to install them on new machines they all failed to bring up teh End User License Agreement and did not register with Microsoft. They were good counterfeits but they were a fraud. I got my money back and the seller did refund PayPal. It is safe to shop on EBay but with software the advice on this page should be followed.

March 23, 2010 9:05 AM

In my opinion purchasing products from ebay is good because i also purchase some products and software from ebay. These are original no duplications. I agree with that also some times some sellers are there on ebays are doing scams with buyers and that's why peoples are not going to buy products there. But it has rarely done. I know about a website which provide online electronics products and software & hardware. If anyone interested to buy then visit on

February 29, 2012 11:42 AM

DON'T EVER buy software on eBay - you are completely unprotected. Here is my situation. I purchased an Adobe product on ebay. It installed fine and worked for years, but then I decided to de-activate it and install it on a different computer and found out that it was a fraudulent serial number. Adobe refers me to eBay and eBay's buyer protection plan only covers 45 days. So if you buy software on eBay you are never know if your software is valid. And eBay refuses to do anything about it.

January 24, 2013 10:56 AM

Not to mention these jerkwads wanting top dollar for abandonware 75 bucks for win 98 or 2000 pro. With?? Greedy little jerks!

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