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I am having difficulty understanding why anyone would purchase the retail version of windows when the OEM version does not seem to be very different. For example, at the time of writing this, I see the difference on amazon to be $130 for the OEM license and $190 for the retail license.

After doing quite a bit of research, it looks as though OEM can only be installed one time, on one machine, and that this is the real advantage of the retail version, that it can be reinstalled multiple times.

Here's the catch. OEM copies CAN be reinstalled on different hardware. Microsoft even has support links on their website explaining how to do this. The key is to make sure that the license is fully deactivated and that only one copy of the OEM license is active at any given time. Link

If I am buying Windows 10 Professional for a small business and they need 8 copies for example, why would I buy an OS that is $60 more expensive per copy when there does not appear to be any obvious difference between them (other than maybe the OEM version may be more of a pain in the rear in the unlikely scenario that I need to swap out a failing motherboard).

  • You appear to be misinterpreting the flexibility they offer people repairing their PC, granted out of necessity, with benevolence or acquiescence. You are not permitted to move OEM licensed products from PC to PC, even though you can probably get away with it. OEM licensing is based on the pairing of the computer purchase with the OS purchase, so that they have identical lifetimes. Repairing the computer is one thing, replacing it is another. – Frank Thomas May 11 '19 at 5:34
  • So, if this is an unlikely scenario - which it is, these workstations are not really in need of any upgrades any time soon, then buying an OEM is probably fine. Given that if the motherboard were to fail, it would be a repair and not a replacement. Is that fair to say? I want to make sure I am being clear that I am not trying to 'work around' any licensing agreements or do anything even remotely illegal. Just trying to understand. – Iofacture May 11 '19 at 5:38
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    I buy OEM OSes when appropriate, so no reason not to in your situation, if you think its right for you. I just don't agree with the basic premise that there is no meaningful difference between the OEM and retail skus other than the price. – Frank Thomas May 11 '19 at 5:41
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    The OEM version also offers no technical support from Microsoft. For the technically adept maybe this is no issue. I've never called Microsoft for any support. But you're talking about a small business who has no IT department and may need support from Microsoft. Although I generally agree with you that the cost savings makes the OEM version a more attractive option in a lot of cases. That would probably be my choice, but I can understand why some would rather go with the retail version. – n8te May 11 '19 at 5:43
  • Frank or n8te - if you make that your answer I will accept it - I can see your logic and agree that perhaps there was an implicit assumption in my question that did not take that into consideration – Iofacture May 11 '19 at 5:47
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A few key things that the Terms and Conditions for an OEM key states that:

  1. OEM versions do not offer any free Microsoft direct support from Microsoft support personnel

  2. OEM licenses are tied to the very first computer you install and activate it on

  3. OEM versions allow all hardware upgrades except for an upgrade to a different model motherboard

  4. OEM versions cannot be used to directly upgrade from an older Windows operating system

With any key, I have never used services from option 1. However, I have bypassed option 2. and 3. I just had to call a number, talk to someone and I had to enter some sort of validation. It's been a while since I've had to do that, but the process wasn't too complicated. They did ask why I replaced the board, and each time it was due to the board failing. All of the times I did this, I worked at a PC repair shop. I'm not sure what they would have said if it was just a board to upgrade to something new.

Somewhere in the Terms and Conditions, there is a limit to how many times you can reactivate an OEM key. I don't know what the magic number is.

As far as option 4. goes, I think the only time that worked well without having to get a new key is when Microsoft was basically letting anyone and everyone upgrade to Windows 10.

I myself got the Windows 7 retail version when I built my PC several years ago so I wouldn't have to worry about reactivating if I changed hardware. With that one purchase. While on Windows 7, I had to RMA a motherboard once. I also took advantage of upgrading to Windows 10. I've upgraded my CPU and motherboard since then and had no problem with reactivation.

To me, it was worth the extra bit of money to avoid some potential hassle, or possibly being denied a reactivation.

Here's a link with some easy to read OEM Software Licensing: Rules & Restrictions

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  • I appreciate your time - this information has been very helpful – Iofacture May 11 '19 at 17:05
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A very important note is vs osm vs retail is the retail version updates any updates that were added to the iso that you can download. I've installed an OEM version of windows and after it was installed, there were 287 updates,OEM version and (177 on the retail version)then I installed windows 7 retail that was given to me by a close friend that works for Microsoft. I love the retail version, that I can download the latest version of windows 7 with all the updates. I know I can slip stream the updates to the OEM version of Windows (windows 7 professional in my case. ) retail version is just simpler in my option.

On a different note. I wanted to upgrade window 10 from Windows 7. And while it seemed to work for a couple of days. It now hangs for a very long time. Figuring I just go back to windows 7, it say my retail key is incorrect. I've got a call back at 10:30 am from Microsoft to reactivate the retail key that that came with the cd.

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  • It's really not recommended to upgrade from 7 to 10 as Windows 7, and even some Windows 8, drivers are not compatible with Windows 10 and will result in instability... backup the data on Windows 7, use Belarc Advisor to generate an HTML report of all installed software and license keys, then clean install Windows 10. Once clean installed, you'll no longer have issues from the drivers that are causing the hangs. Windows Update will install all non-CPU (chipset, IMEI, etc.) related drivers, and it's recommended to install CPU drivers first. – JW0914 Nov 20 '19 at 14:44
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    Just an FYI, Windows 7's EoL [End of Life] is in two months, at which point it will cease to receive security patches from Microsoft (unless you're a business with a LTS agreement). Whenever security updates are released for Windows, it will usually provide a direct line of info on what to exploit on Windows OS versions that are EoL and no longer receiving the patches. – JW0914 Nov 20 '19 at 14:47

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