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Have an old(ish) laptop with a Pentium T4400 @ 2.20 GHz processor, and some old software1 that requires Windows 95 or NT.

With a view to running this software on that hardware, I tried installing Windows 95, 98, ME, 2000, and NT from CD-ROM with no success whatsoever.

Can it be a configuration problem? Which is the latest processor I can use for this software?

IIRC, Windows 98 & ME are versions of 95, and 2000 is a version of NT? Later Windows versions are more different?


1 The software in question, which does not run on Windows 7 or 10, is Nationalencyklopedin:

In 1997, the first digital form of the encyclopedia was released on 6 CD-ROMs...

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    A screenshot of it makes it look like it might a 16-bit program, in which case you would need a 32-bit version of Windows 7 or 10. – Ross Ridge Nov 1 '18 at 16:14
  • Those considering this question off-topic: why? Is it because it's a general software-compatibility question? If so, it could form a useful canonical for duplicates to be closed to. – wizzwizz4 Nov 1 '18 at 20:16
  • @RossRidge or XP Mode inside 7 – manassehkatz-Reinstate Monica Nov 2 '18 at 1:18
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    Would running an older version of Windows in a virtual machine on a newer OS be an option? – Thorbjørn Ravn Andersen Jul 22 at 9:46
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Windows 2000 is the latest (5.0) version of NT. Last Update was 2005, EOL in 2010. The Laptop isn't anywhere near being old (or OT here), as its at maximum from 2010. While this seem late, it should be possible to install Win2k, update it to SP4 and include drivers for the Laptop from XP, as the original XP driver model is still compatible with NT/Win2k.

Then again, without more information why installation failed, it's hard to even randomly guess why it doesn't work.

Further, software made for NT should, in most cases, run on XP and even Windows 10. Of course, depending on what OS services it uses. So again, without a more detailed information about it's impossible to give a real answer.

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    "Windows 2000 is the latest (5.0) version of NT" ... from a certain point of view. Of course, Windows XP is NT 5.1, if you ask it for its version number ... – Jules Nov 1 '18 at 19:31
  • Well, at that point I go with Microsoft, who marketed W2K as NT - while XP was defined as being an NT replacement - and realy did offer new structures. Furtehr, the Version number isn't any indication here, as it's a continued scheme since Windows 1.0 – Raffzahn Nov 1 '18 at 21:05
  • The first release version of Windows NT was 3.1, which was followed by 3.5, 3.51, 4.0, before it became Windows 2000, before it became Windows XP, before it became Windows Vista, before it became Windows 7, ... The DOS-based Windows lineage (1.0, 2.0, Windows/386, 3.0, 3.1, 3.11, '95, '98, ME) is a different product with a different code base. I distinctly recall Microsoft branding Windows 2000 as "built on NT technology", so I guess one could argue both ways whether it's Windows NT or not. Wikipedia says that beta 3 onward, Microsoft called it Windows 2000, as opposed to Windows NT 5. – a CVn Nov 2 '18 at 10:26
  • The software may check the Windows version by reading a particular version string from the registry, instead of looking at a version number. If the software expects to find "Windows 95" or "Windows NT", it won't recognise " Windows 2000" , even though it's the successor to NT 4.0. This is also why Microsoft went from Windows 8 to Windows 10: a lot of older software assumed that if the version string started "Windows 9..." that it was Win 95 or Win 98, and refuse to install. – Kaz Jul 13 at 12:57
  • I am of the camp that says Windows 10 is NT regardless of whatever marketing calls it. It's the same kernel design and (if one had access to the source code, which I do not) one would probably still see "NT OS/2" written in some header comments. – another-dave Jul 13 at 13:07
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Windows XP Mode

Quite a bit of older software will NOT run natively in Windows 7 or above. However, most of this software, whether DOS-based or older Windows software, will run just fine in Windows XP Mode.

Unfortunately, Windows XP Mode is not available for Windows 10. I have quite a few customers where I have stuck with Windows 7 specifically in order to run Windows XP Mode to run older software. Actually, most of them (and many of my other customers) prefer the "classic" Windows interface used from 95 through 7 to the newer 8/10 interface anyway, but I digress.

Other than the now very rare (for me at least) hardware issues requiring older systems to run properly, I have not had any significant problems getting the oldest software - including much that would quality as Retro (> 20 years old) running well in Windows XP Mode in Windows 7.

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    Also I prefered that GUI, imho the m$ gui design did not develop since win98. Currently I use ratpoison on linux. :-) – peterh says reinstate Monica Jul 22 at 16:40
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You mention the processor but not the amount of memory installed. It's possible that it contains more RAM than older versions of Windows can deal with.

You could try using a virtual machine (VM) such as VirtualBox which can be configured to support older versions of Windows with a single CPU and a small amount of RAM (512MB might be a place to start). Your preferred flavor of "classic" Windows should install with little issue.

Then you can mount the media for your software within the VM and install it.

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IIRC, Windows 98 & ME are versions of 95, and 2000 is a version of NT? Later Windows versions are more different?

All modern windows is based on the "NT line", but of course it has evolved over the years and sometimes things break.

IIRC in terms of windows system stuff NT4->2K was a pretty big change, 2K->XP was realtively minor, XP->Vista was a big change and Vista->7->8->10 were again relatively minor.

Can it be a configuration problem? Which is the latest processor I can use for this software?

It's not so much about the processor as about the whole system. PCs aren't fundamentally all that different from they were in the 2000s, but there are enough little things that can make getting older OS's to run on newer hardware difficult or impossible.

It's worth trying windows XP if you haven't already. It might be old enough for your software to run, while being new enough for the rest of your hardware.

It's also worth setting the SATA mode to "legacy" in the BIOS.

Failing that it is worth considering virtualisation, virtualisation tools (virtualbox, vmware etc) often get on better with older operating systems than real hardware does.

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