An enterprising UK IT user who goes by "The Rasteri" on YouTube has completed an incredible "experiment" [video], in which he installed every major version of Windows, upgrading, in order of their release, inside a virtual machine.

He describes in the video, "It is hoped that this will shed light on how the Windows upgrade process has changed over the years."

For his testbed he used a machine running VMWare.  He says he selected VMWare based on its snapshot and video recording capabilities.  Also, importantly, VMWare offered full support for all legacy Windows operating systems.

I.  Early Windows -- a Slow Evolution

To start, he installed MS-DOS 5.0 on the virtual machine, as most early versions of Windows required it as a starting point for installation.  He describes, "Installation was surprisingly easy for an operating system of this age.  It even partitioned and formatted the hard drive."

He shows off the MS-DOS shell, which, while offering a GUI, was not a true relative of Windows, in his opinion.  Before installing any version of Windows he installs a couple of games -- Monkey Island and Doom 2.

Windows 1.0 -- of Ballmer sales infamy -- was then installed, with EGA graphics (Windows 1.0 predates VGA).  No pointing device was selected as serial mice were the only options and VMWare doesn't support them.

He then breezed through Windows 2.0 (which supported VGA and PS/2 mice).  He then verified the games installed on DOS were still compatible and admired at the new printer settings.  Notably, Windows 2.0 did not copy over the windows.ini config file from Windows 1.0.

Moving ahead, he started installing Windows 3.0.  He notes that it preserves the Windows 2.0 windows.ini file, though it was unable to automatically detect the DOS games.  He was able to reach the games by going in to the program manager and manually creating new program instances.

Windows 3.1 was then installed.  While Windows 3.0 merely preserved the color scheme, Windows 3.1 preserved the keyboard and display settings, as well.  It also requested a user's name and company upon installation.  It also preserves the program groups that were hand-created in Windows 3.0.

Next up was Windows 95.  To get there, he had to install MSCDEX CD drivers to install.  He calls the setup procedure "very well polished compared to previous version and clearly intended for novices to be able to perform."  The setup reportedly took 30 minutes.  This OS introduced right click menu bars.  Program Manager groups were auto-converted to start menu objects.  The previous DOS Shell worked even though it was not included with the install.

Next up was Windows 98.  As there was no upgrade version, he installed a full install process.  The process took an hour and a half.  But all programs still launched correctly, at least.

Installing Windows 98 SE, the time was almost as painfully long, but it could be installed directly from within Windows 95. According to Rasteri "nothing of note changed."  

II. Entering the NT Era

Moving on to Windows 2000, the first NT-based operating system installed.  Like Windows 98, an upgrade CD wasn't available, but at least the CD could run from within Windows 98, as with the Windows 95 to Windows 98 SE upgrade.  

Rasteri notes the fast install time (45 minutes) and auto account setup as perks.  Desktop colors from Windows 2.0 were preserved (in effect) 13 years later.  The background was now displayed in beautiful undithered glory.  This was due to an increased default display bit depth. Downsides include that the games would hang due to poor DOS support.

Windows XP SP3 would not install, so SP2 was used.  The theme was reset to a "Luna" theme, scrapping the old themes.  And the install took 1 hour and 10 minutes.  But at least Doom 2 and Monkey Island worked again, due to improved DOS support.  The pink color scheme was re-applied for testing's sake.

Installing Vista via DVD took "the longest yet" -- two hours.  The color scheme was again scrapped.  Mr. Rasteri unfortunately fails to note whether Doom 2 and Monkey Island still worked (we're guessing they didn't).

Finally he arrives at Windows 7, Microsoft's current OS.  The color scheme was dropped yet again, but at least the program groups were still properly preserved.  Legacy applications in the Windows folder like "Cardfile" and "Calendar" were surprisingly preserved.

Recorder, Terminal, and ("can you believe it!?") Reversi were also included.  The hard drive volume was labeled MS-DOS 5.

III. Conclusions

As Rasteri concludes in the video, fascinatingly this test confirms that a great deal of information, including program groups and installed files, can pass from Windows 1.0 all the way to Windows 7.  Certain features like the screen themes, though, were scrapped at multiple steps along the way, due to display changes.

If nothing else, the video is worth a quick watch as, well, we virtually all use Windows.  For most, it will be a real trip down memory lane.

You might have noticed that the much-loathed Windows ME, released in 2000, appeared to be purposefully excluded from the succession line.  Windows ME essentially crippled many DOS applications, among the reasons for its dirt-poor reputation.   

The only think to truly cap this incredible upgrade experiment would be to go and watch current Microsoft CEO Steve Ballmer selling Windows 1.0 in his younger years [video]!