virtualbox.org

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 Windows 1.0 Windows 2.0 Windows 3.1 Windows 95 Windows NT 4.0 Windows 98 SE Windows 2000 Windows ME Windows XP

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.

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.

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.)

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.

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).

Right... So, if I don't install NT and ME, what's the easiest way? Does it work to directly install 2K to 98? I know when I was little I used to have an old HP Invent Pavilion PC running Windows ME that got upgraded to Windows XP Service Pack 1 when it first came out...

Good luck.

Windows 2000 (Windows NT 5.0) was the successor to Windows NT 4.x, NOT Windows 98, so "No" it was not a direct upgrade path as its main market was the 'business' sector.

See: https://en.wikipedia.org/wiki/Microsoft ... on_history

IMO you should forget about 'upgrades' and (attempt to) install each version you want to re-visit separately, after researching their hardware requirements and obtaining the required installation media, especially as early Windows versions were also frequently matched with different versions of DOS.

Ryguy wrote:when I was little I used to have an old HP Invent Pavilion PC running Windows ME that got upgraded to Windows XP Service Pack 1 when it first came out...

I could easily see this happening, as Microsoft wanted to get everyone to NT, so they could program such an upgrade channel.

In fact all upgrade channels (even downgrades) can be programmed for. Windows 1.0 to Windows 11? Yep, just gather the developers and a load of cash and go to it! Not much business sense in it, but it is possible.

However, not all these upgrade channels were programmed, so some of the proposed steps in your project may not be possible.

The coolest idea about this topic is that you have a unique opportunity to tell the forum what does work. Try the various upgrades, take backups for rollback purposes if something goes wrong, and let us know what you discover.

I don't remember an upgrade path from ME to XP ever existing. I think what the OP (mis)remembers as an upgrade would have been a complete wipe of the hdd followed by an install of XP.