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I'm wondering what the best way obtain old versions of Windows would be, specifically:

  • DOS
  • Windows 95
  • Windows 98/SE
  • Windows 2000/ME
  • Windows XP Professional
  • Windows 7 Professional
  • Microsoft Office for each version of Windows (i.e. Office 98 for Windows 98)

I would need both the physical install media/ISOs and the activation licenses. There are some of the options I've been considering:

  1. Call Microsoft up and offer to pay them a lot of money to get copies and licenses for these versions of Windows, since they probably have some massive archive of everything in some basement. (Can they refuse?)
  2. Spend weeks scouring eBay and Amazon on the off-chance someone is selling a copy and buy it before someone else snatches it up.
  3. Use sites like https://winworldpc.com/library that are questionable legally. It looks like they provide the install files but not the licenses for obvious reasons. They all have Microsoft Office install files.

I'd preferably like to obtain them legally, just so I'll be able to sleep at night and so I can get 100% functionality with all of the software, including the ability to join (at the very least) the XP and 7 machines, and maybe the 2000 machines, to a domain. I would install all these operating systems on actual hardware from that era, not use virtual machines on modern versions of Windows or emulators.

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    You may want to re-word this question. Opinion based questions like these are generally off-topic. Plus, I believe it's frowned upon to ask where to obtain software. Anyway, having said all of that, I personally feel that eBay is your friend here. You can find unopened (and supposedly not used) copies of software all the time on eBay. Which should be legit because the license was never used. But this would obviously depend on the seller being honest.
    – cbmeeks
    Commented Aug 2, 2017 at 15:00
  • If you can get yours hands on the installation media, I think many of the older products can be activated with a license key of all 1's or some trick like that. I'm not sure of the history, but it was some trick that MS left in there to help with massive installations. Of course, you're not really "legal" at this point, but if it is just for testing purposes it will suit the purpose.
    – bjb
    Commented Aug 2, 2017 at 17:09
  • @InterLinked with old windows systems, the liscense/product keys aren't accociated with a particular machine or database, so technically you could use a single product key for multiple systems with the same OS up until Windows 7. Windows 7 starts to implement the 30-day trial without a new valid product key. See: (retrocomputing.stackexchange.com/questions/775/…)
    – Retro Gamer
    Commented Aug 22, 2017 at 16:35

2 Answers 2

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The legal way to obtain old versions of Microsoft operating systems and software is to buy a Visual Studio subscription (formerly known as MSDN subscription). That page has a link to the complete list of available software, which includes (as of January 2022)

  • MS-DOS 5.0, 6.0, 6.2, and 6.22;
  • Windows 3.1, 3.11, 3.2, and Windows for Workgroups 3.11;
  • Windows XP and later;
  • Office 95 and later (excluding Office 97);

Windows 95/98/ME, NT4 and 2000 are no longer available. (Windows 95 was removed in 2001, the rest in 2003 following settlements with Sun Microsystems.) For those you’d need to find a second-hand copy whose licence allows it be re-sold (so probably not OEM versions), or buy an older computer pre-installed with the right version.

In any case you’ll need to check the licenses. A subscription gives you a perpetual license to use the versions available during your subscription, as well as downgrade rights, but only for development and testing purposes; this whitepaper gives more details but you’d have to check an actual contract to be sure.

(Thanks to Euro Micelli, PeterI and Ross Ridge for their insightful comments.)

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  • That's an odd thing to buy, but if it works I'd do it. Can I just subscribe for one billing cycle, download and install everything I need, and then cancel my subscription?
    – InterLinked
    Commented Aug 2, 2017 at 11:10
  • Read the fine print very carefully. As far as I know, that gives you access to the installers, but does not give you a "production" license. You are only authorized to run the OS software for "development/testing purposes" (for example, maintain drivers for an ancient device that has to run under old versions of DOS or Windows). A "production" license is needed to actually "use" the OS for, you know, anything other than "testing something on it". That still requires a separate agreement from Microsoft. You'll have to talk to them.
    – Euro Micelli
    Commented Aug 2, 2017 at 12:06
  • The version I have doesn't have downloads for older windows versions, pretty sure a couple of years ago you got Windows 9x but these days it's just MS-DOS 6.0, MS-DOS 6.22 and Windows 3.x.
    – PeterI
    Commented Aug 2, 2017 at 15:10
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    @InterLinked If you subscribe to the correct version then you have a perpetual licence that continues after the subscription ends. You just don't get a licence to any new software released after that. The subscription also gives you "downgrade rights" and lets you use older versions of software that's included in your subscription, including older versions no longer available for download. You'd you need to obtain the media yourself somehow. As Euro Micelli noted the licence for the licence is only for development and testing using the operating systems included.
    – user722
    Commented Aug 2, 2017 at 15:30
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    With OEM versions, it depends on locality whether an OEM EULA can or cannot forbid reselling/reusing it once the original hardware is decommissioned... Downgrade rights, btw, are also commonly included if you buy any OS license under a volume license program like "open license" (which you are IIRC applicable for if you initially buy at least 5 products - and luckily, most software resellers who have OL products will have some low priced, obsolete items in their catalog to fill the other 4 slots ;)
    – rackandboneman
    Commented Aug 4, 2017 at 21:10
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I have been able to find factory sealed copies of Windows 95, 98, 3.1, DOS and NT at various thrift shops (example: GoodWill) in my area, with product key inside. There are also tons of these on eBay. I think it's reasonable to assume that they are genuine since I throw them out at work all the time and there's low demand, thus low chance of fakes.

As for Windows 7, go to MSDN.

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    Don't destroy them! They are a finite resource, and of historical interest! Plus, you might be able to sell them for enough for it to be worth your while.
    – wizzwizz4 ♦
    Commented Sep 9, 2017 at 8:38
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    A quick check on ebay shows the market price of an original win98 cd is about $40.
    – peterh
    Commented Mar 9, 2020 at 13:18

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