How to get old versions of Windows working

Every long-time PC user has their own memories of the days of 286, 386, and 486 processor home computers. But how was that again exactly in Windows 3.1, 95, and 98 or later XP? Immerse yourself in the IT past with us.

We show how to revive old Windows versions or tools. ©ilterriorm/Shutterstock.com

Retro technology is considered chic and is particularly popular with young people. This is particularly visible in the return of vinyl records and turntables: LPs have long been available again in many places, and the traditional manufacturer Dual now has twelve turntable models in its range.

In addition, there are many other device classes in retro design from other manufacturers, including cameras, the classic mobile phones from Nokia, the Sony Walkman, radios, game consoles, PC keyboards and mice, cassette players, and more. As beautiful as the memory of the technology of the past is, its usefulness is often limited. Because the functions have long since been taken over by PCs, smartphones, etc., in addition to the initial investment, there are sometimes considerable follow-up costs. Instant camera “film” and vinyl discs, for example, are anything but cheap. This is different from the old versions of Windows, games, software, and websites. You can immerse yourself in the past for free and without much effort.

Windows is already approaching 40: from version 1.0 to 11

Windows was presented to the public in 1983, but version 1.0 was only completed two years later. 
At the time, the system had to be installed from 5.25-inch floppy disks.

The beginnings of Windows were difficult. When Microsoft founder Bill Gates presented the first prototype of his operating system at the Computer Dealers’ Exhibition (Comdex) in 1983, there was no competition with which Apple Lisa already had a home computer with a graphical user interface as a competitor. It then took another two years until the user interfaces for MS-DOS – more was Windows 1.0 was done. It was initially unsuccessful, there were hardly any applications, and the computers were still expensive at the time. Microsoft only had a breakthrough with Windows 3.0 and 3.1 from 1990 and 1992 respectively. The versions offered significantly more comfort and even functions that are still in the current operating system: including the program and file manager, the control panel, and some games.

For the first time, Windows 95 also brought home users the benefit of 32-bit support, which was previously reserved for companies in Windows NT (“New Technology”). Three years later, Windows 98 came onto the market, and in 2001 the successor versions 98 SE and ME were the last DOS-based versions. Windows XP relied on a much more reliable and stable NT basis in 2001. Technical progress and the success of this system can also be measured by the fact that Microsoft has extended support for XP several times. It wasn’t until 2014 that it finally came to an end.

Remembering the almost 25-year-old DOS-based operating system. Windows 98 runs in the DOS emulation DOSBox-X on a modern PC with Windows 11 without any problems.

The successor Windows 7, for which Microsoft provided security updates until 2020, was similarly successful and popular. Anyone who had to migrate to Windows 10 at the time could at least upgrade for free. The interim versions Vista, 8, and 8.1 had little success. Currently, Windows 10 or 11 can currently be used. Because support for the previous version 10 runs until October 2025, there is currently no pressure to switch to the newer version. You can read more about the history of the Microsoft operating system here. If you want to go back in time and see Bill Gates at the Comdex show in 1983, check out the video from back then of the installation of the different versions. The almost 20-minute video compilation “Upgrading from Windows 1.0 to Windows 10” is also interesting: it shows a brief summary of each.

Try Windows in virtual PC, DOS, or web emulator

When trying out or using different operating systems in parallel, one automatically thinks of virtual systems. However, this is not quite as easy as it is today with the early Windows versions. Simply booting a virtual machine from an ISO file does not work because the graphical DOS interface used to be supplied on floppy disks. After all, this problem is with Winimage resolved quickly. However, virtual systems are not the first choice here because there are often problems. Finally, we come back to installation and operation.

Windows 3.1 as an emulation in the browser: Not only does the operating system seem downright antiquated, but so does the resolution of 640 by 480 pixels, including the 4-to-3 format.

The DOS emulators DOSBox and DOSBox-X are less complicated, although the command line commands and settings in the Autoexec.bat, Config.sys & Co. files may no longer be familiar to some former DOS users. The graphical DOSBox control surface is therefore helpful D-Fend Reloaded is therefore helpful, it does a lot of configuration work for you. In D-Fend Reloaded it is sufficient to import a DOS application, for example as an archive file in ZIP format, and then start it. If you want, try a free game from the DOS Games Archive

To start a previous version of Windows in the DOS emulator, you must first have the data in the appropriate format. To do this, google the desired Windows version together with the search term “Dosbox”. As an example we choose Windows 98 from the Internet Archive: Download the “WinBox98SE.zip” zip archive, unpack it and start the Windows emulation by double-clicking on the “dosbox-x.exe” file. This starts an almost fully functioning operating system. There are only a few restrictions, for example setting up additional hardware, because you would need the original DVD for that. 

Tip: Use the shortcut Ctrl-F10 to move the mouse out of the DOS emulation to control your actual computer again.

Windows 95 also exists as a portable app for easy testing on Windows 10 and 11 and is available on GitHub.

Start early versions of Windows directly in the web browser

As a further option in addition to the virtual PC and DOS emulator, there are ready-made Windows emulations that run directly in the browser. This is particularly convenient because you don’t have to install or configure anything here: enter the URL in the address line of the browser, start it, and off you go.

The PC emulator PCjs stands out. The Javascript-based portal offers various Windows systems from the first version up to Windows 95. To start, select a variant via “Highlights” on the start page or in the list on the left via “Software -› Systems -› Windows”. Another mouse click and a moment of patience are enough for the respective system to run in the window on the right. Here, too, you can operate the systems of the time almost completely and take you back to the 1990s.

The Windows systems can be customized with software in the PC emulator PCjs and saved locally so that you can continue working with them later without reconfiguration.

PC is interesting beyond the finished versions of Windows because the virtual floppy drives provide access to over a thousand old floppies: from Borland Turbo Pascal to Word for Windows, you can install many old applications. If you have managed the software setup as before by changing the respective installation diskette, you do not need to start all over again the next time. Use the “Save HD” function below to save your individual system as an IMG file locally on the hard drive and start it again from there at any time with Virtual Clone Drive.

PC is not only limited to Windows installations but also emulates other operating systems, hardware, and software and includes guides, documents, and more.

Windows 3.1 and 95, the two most important versions of that time, can be found emulated in German on Winhistory. There you click on the “Virtual PC” link on the start page and select the desired variant. The newer versions of the operating system – including the Windows 98, 98 SE, ME, 2000, and XP systems – can be downloaded from the Virtual Desktop website start. To do this, follow the “Complete Desktops” link and then select the desired system. 

Windows 1.0 to XP as a virtual machine on the computer

Finally, we come back to the possibility of running earlier versions of Windows on a virtual PC. As an example, we do this again with Windows 98 in Virtualbox. Be forewarned that it doesn’t work that easily on some machines: Depending on the hardware and UEFI, it can be extremely tedious to install the virtual Windows system. Alternatively, try it with VMware Workstation Player.

This is how it works: Install Virtualbox and then save the ISO image of the Windows 98 CD-ROM on the hard drive. You can easily find this on the Internet, for example in the Internet Archive or in the WinWorld “Library”. . Start Virtualbox, click on “New” in the program interface, and enter “Windows 98” as the name in the next field and confirm the next steps. Before you install the virtual PC with Windows 98 via “Start”, click on “Change -› Mass storage”. It continues with a mouse click on “empty” at the CD symbol in the middle and then on the CD symbol on the far right. Here you continue with “Select/create virtual optical medium” and mount the previously downloaded ISO file. Now close all windows and start the Windows installation on the virtual machine. Incidentally, you need a license key from Windows 95 onwards. You can quickly find it on the Internet to try it out with the keyword “Generic Key”.

We didn’t count a large number of confirmations – it takes a while for the old Windows to start for the first time. After completing the installation, it is recommended to install a new graphics driver (for Windows 95/98). This increases color depth and resolution, making work much more pleasant. 

Old software and games in compatibility mode

If outdated programs do not run or do not run properly under Windows 10 and 11, the compatibility mode can solve the problem.

In addition to the option of running outdated games and software as described in the DOS emulator or a virtual PC with an “old” operating system, Windows 10 and 11 still offer compatibility mode. You turn this on by right-clicking on the link or executable file of an installed program, continuing with “Properties” in the context menu, activating the option of the same name on the “Compatibility” tab, selecting a Windows version, and changing the settings with Confirm “OK”.

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