The Perfect Route

Discussions about using Windows guests in VirtualBox.

The Perfect Route

Postby Ryguy » 3. Oct 2022, 01:40

Hey, does anyone here know the perfect way to install all the good Windows ISOs up to XP in order without it crashing or causing errors? The order I'm thinking of is:
MS-DOS :arrow: Windows 1.0 :arrow: Windows 2.0 :arrow: Windows 3.1 :arrow: Windows 95 :arrow: Windows NT 4.0 :arrow: Windows 98 SE :arrow: Windows 2000 :arrow: Windows ME :arrow: Windows XP
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Re: The Perfect Route

Postby scottgus1 » 3. Oct 2022, 02:39

Ryguy wrote: install all the good Windows ISOs up to XP in order

All in the one VM?
Ryguy wrote:Windows 95 Windows NT 4.0 Windows 98 SE Windows 2000 Windows ME Windows XP

If I recall correctly, 95, 98, ME are DOS-based, & NT, 2000, XP are NT-based. Was there an upgrade method back-and-forth between DOS & NT & back? DOS-based couldn't understand NTFS, so you can't go from NT to DOS if you upgrade the filesystem from FAT to NTFS.
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Re: The Perfect Route

Postby AndyCot » 3. Oct 2022, 03:56

Some of the OS's listed are dead ends in that there is no complete upgrade path to the next version. By complete I mean that the apps and settings will survive, but you can install the next version and it will blow the old version away.

You are better asking MS what the upgrade/update process is and where it is documented. Once you get the MS documents and process then come back and ask how you it can be done with Virtualbox using the MS process you find.
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Re: The Perfect Route

Postby Ryguy » 3. Oct 2022, 04:28

Oh. I guess I might as well give up after doing that since 2021. I guess I should download each individually reeeeeeeeally carefully. (I asked that since upgrading from Windows ME to Windows XP worked when I was little, and that kept all the files.)
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Re: The Perfect Route

Postby mpack » 3. Oct 2022, 10:32

scottgus1 wrote:Was there an upgrade method back-and-forth between DOS & NT & back?

Nope, there was not. NT4 and Win2K were seen as business solutions, Win98 was the home solution. The two markets did not converge until XP Home, and it was a switch, not an upgrade. In fact the DOS branch continued with ME before dying.

Also the earliest versions would be problematic too: Windows 1 and Windows 2.x were (I believe) real mode GUI environments for DOS, not OS's, so I would not expect the upgrade path to be very easy at that end either. And that's assuming a semi automated installer exists, a big ask back then.
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Re: The Perfect Route

Postby AndyCot » 3. Oct 2022, 10:56

Got to watch Windows 1.x and early Windows 2.1 versions as they were packages as part of the GUI app from my memory when I first "used" Win 2.1 or was it 2.1.1 (I think). Up to and including Windows ME they ran on top of DOS. Windows NT was a separate OS that was based on OS/2 and did was a stand alone OS. NT morphed into 2000 and XP (2000 was for servers and XP for desktops, but shared allot under the hood).
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