Loading Windows 3.11, 95, ME and XP In VirtualBox

Windows 3.11 running in VirtualBox

For many of us, this was our first experience with the Microsoft Windows graphical user interface (GUI).  Windows 3.1x was nothing more than a graphical shell around which DOS operated.

Thanks to VirtualBox, you can relive that nightmare all over again!

If you know nothing about VirtualBox, now would be a good time to learn.  An image file (.img or .ima) can be used as a substitute for physical floppy disks in VB.  You swap image files under the Devices menu at the top of the screen while VB is running.

Before attempting to load Windows 3.1x or Windows 95 in VB, you must disable VT-x/AMD-V and Nested Paging under the System > Accelerations settings tab.

A full tutorial has been created by Glijnos to walk you through the process.

I have all of the images files for DOS 6.22 and Windows 3.11 that were included with my first Windows computer: a Packard Bell Legend series system with a 50MHz Intel CPU, 4MB of RAM built onto the motherboard (upgraded to 36MB by adding two 16MB RAM chips), and a 512MB hard drive.

How cool was that?

Program Manager Windows 3.11 About Screen

Not very.

Why would anyone want a working virtual copy of Windows 3.1x?  Well, perhaps you have a bunch of old software programs lying around and just need to open a document in Microsoft Works 3.0:

Microsoft Works 3.0 in Windows 3.11

Or maybe you just want to see the Berkeley Systems After Dark Loony Tunes screensaver you bought years ago run just one last time:

Looney Tunes After Dark Screensaver

That Pepé Le Pew sure was a scoundrel!

Pepé Le Pew After Dark Screensaver

Or you just want to rekindle old skills you’ve forgotten.

Or you’re like me and you have a bunch of old Windows install discs collecting dust that are just begging for new life.

Windows 95:

Windows 95 running in VirtualBox

Historically significant, Windows 95 set the standard for the desktop GUI.  It was also insanely unstable.  Even in VB, it may still give you fits.

Create a new VB install.  Set the virtue hard drive (.vdi file) to a fixed size of no more than 2GB.  Set RAM to 32 or 64MB.  Set video RAM to 32MB.  Remember to disable VT-x/AMD-V and Nested Paging.

If you have a full Windows 95 install disk (OEM disks or full commercial release), load DOS 6.22 just as you did for Windows 3.1x.  Add the  cdrom.img files to the completed install.  Now you can reboot your virtual install and use your Windows 95 disc to install the OS.

Windows ME:

Windows ME running in VirtualBox

One of the most hated operating systems in Microsoft’s history, Windows ME still gives users headaches when trying to do a VB install.  But I found a way around that problem.  Install Windows 95 first and then upgrade.

Here we go again!  Create a new VB install.  Set the virtue hard drive (.vdi file) to a fixed size of 8GB.  Set RAM to no more than 512MB.  Keep the video RAM at 32MB.  Remember to disable VT-x/AMD-V and Nested Paging.

Load DOS 6.22 just as you did before for Windows 3.1x.  Add the  cdrom.img files.  Now you can reboot your virtual install and use your Windows 95 disc to install the OS.  Once installed and booted, insert your Windows ME disc (full, OEM or upgrade) and follow the onscreen instructions.

When Windows ME finishes installing and completes a first boot, shut it down and enable VT-x/AMD-V and Nested Paging.  This will speed up ME in VB.

When you loaded Windows 95 in this install, it created a virtual hard drive of only 2GB, but our .vdi file is 8GB in size.  How do we get those 6GB back?  With Linux!

Download the 32-bit version ISO image file of GParted.  Or use your favorite Linux distribution Live Boot Disc that contains the GParted program.  Boot your Windows ME VB install into Linux and use GParted to format the unallocated portion of the virtual hard drive to FAT32.  You can name the drive if you wish.

Remove the Linux disc or image file from VB and boot back into Windows ME.

Windows ME My Computer Screen

Your install now has two hard drives!  A 2GB C: drive and a 6GB D: drive are both accessible from within the virtual environment.  Thank you, Linux.

Desktop themes from Windows ME

To activate the desktop themes:  go to Control Panel > Add/Remove Programs > Windows Setup tab > Desktop Themes > Apply.  No disk is required.  The themes only need to be activated to be accessed.  This will add an entry to the Control Panel.

Installing Guest Additions:

Forget it.

None of the preceding operating systems are compatible with the VB guest additions.  However, you might manage to get part of the guest additions to load in Windows ME before you get an error message.  This will at least load the mouse integration drivers and allow you to automatically “capture” the pointer when hovering over the ME window.

You will have no USB access, no shared folders and no fullscreen integration.  Other than that, it works great.

Internet access may be possible in Windows ME by using the Internet Connection Wizard’s third option and connecting through the local area network (LAN).  Use ClamWin Free Antivirus and the Sygate Personal Firewall to help protect the guest OS.


Video Drivers:

The best video drivers for Windows 95\98 and ME can be found at the VBEMP 9x Project.

Right-click on My Computer > Properties > Device Manager > [+] Display adapters and select the entry under that heading.  Click the Properties button at the bottom of the box.  Click the Drivers tab and then Update Driver… to install these drivers.

I didn’t say it was easy.  But it does work.  Once installed, you can set your screen resolution from 320 x 200 256 colour up to 1600 x 1200 True Colour (32-bit).  Do not use the fullscreen integration feature of VB.

There are three sets of drivers folders provided by the VBEMP 9x Project.  Each folder is marked to the corresponding amount of video RAM you allowed in the VB settings.  If you set the video RAM to 32MB, use the folder labelled 32MB.


Printers in Windows ME

It can be done.  Like any guest OS in VirtualBox, you must add the printer argument to the system through the VB USB settings.  The guest OS must have USB support and recognize that a printer is connected.  The printer must have the appropriate print drivers to install in the guest OS.

The HP Deskjet 5940 originally included Windows ME drivers and software.  Hewlett-Packard also offers additional drives on their website.  Other manufacturers may also offer drivers for older operating systems.

A Few Tips and Tricks:

The easiest way I found to import files into the VB installs is to use AcetoneISO.  This Linux only program can be used to convert a folder and its contents to an ISO image.  The image can then be mounted in VB and accessed by any Windows install as a physical CD\DVD.

Alternatively, you can always burn the files to a blank CD\DVD.

Backup your .vdi file.

If this is your first introduction to VirtualBox, there are some excellent tutorials to help you get started.

Early Windows install disks were not boot disks.  If you are loading Windows 95\98\ME from scratch, you must use the fdisk command from a running boot disk to create partitions on the virtual drive and then format the drive (typically Fat 16 for 95 and Fat 32 for 98\ME) (format c:) before loading the OS.  DOS 6.22 automatically formats before it installs.

Installing old operating systems in VB is a fun way to learn more about the history of operating systems and how they worked.

It can also be useful for playing older Windows-based games that no longer run on newer Microsoft platforms.

The most useful out-of-date OS is still Windows XP:

Windows XP running in VirtualBox

Windows XP has full integration with the guest additions software in VB.  You can backup and port the .vdi file to other computers.  Although Microsoft no longer supports XP, there are still plenty of compatible software packages available from other vendors.

Old Version provides free downloads of older software programs.

For more information about old operating systems, check out the History of Operating Systems.

VirtualBox is a fun tool for exploring operating systems both old and new.  Now, go put those old discs to good use!

VirtualBox Installs of Windows


OS/2 Warp running in Virtualbox

OS/2 Warp running in VirtualBox (click to enlarge)

A VDI version of OS/2 Warp is available at the Internet Archive.

Windows 98/98SE:

Windows 98SE running in VirtualBox (click to enlarge)

Windows 98SE running in VirtualBox (click to enlarge)

The same key code that works with Windows 98SE also works on Windows 98, and vice versa (hint, hint, wink, wink, nudge, nudge — say no more).

You install Windows 98 in the same way you install Windows ME.  It’s fun to play around with, but ME is so much easier to load and run.

Obligatory Disclaimer:  All of these operating systems are obsolete and no longer supported.


7 Responses to “Loading Windows 3.11, 95, ME and XP In VirtualBox”

  1. The Doctor Says:

    Windows 95 through ME did not have native support for the mouse scroll wheel. You must install third-party software.

    The Belkin mouse driver (mouse_driver1.0.exe) will work with any brand of mouse and can still be found at:


  2. Paul S. Says:

    Thanks for trying to help – Has a lot of good info, but can’t get it to work on my mini Mac after 3 times – so I give up! I also tried “Wine”. Wine works great on my Linux laptop. Will try Boot-Camp next. Thank you.

    • The Doctor Says:

      I do not use, recommend or support the Apple/Mac/iOS ecosystem, because it is a closed-source, massively proprietary hardware and software business.

      I tried installing VirtualBox on my Windows 7 computer with limited success. It seems to work best on a Linux OS. So I’m not surprised that you had problems with it on a Mac mini.

      WINE is very limited. The simpler the program, the better WINE works. Complex programs, like games, require additional DLL/DMA support and DirectX driver support that may be too complex for a stripped-down MS Windows layer to handle.

      Windows XP and higher are supported by the VirtualBox guest additions software. Windows ME and below are not, and therefore require third-party software to support hardware functions. Getting older, impractical operating systems to run on today’s newer/faster hardware is more a matter of luck than skill. But it’s fun to try.

      It’s not your fault if it fails to work.

  3. John Says:

    I’ve tried everything I know to make Win 3.11 work and got nowhere after losing several days. I used DOS 6.22 to boot 3.11, I used fdisk to format 1 GB, and nothing. I am done.

  4. Rick Sparks Says:

    Windows 3.11 runs fine in DosBox. With sound and everything, you just have to tweak it and remember to “reboot” for things like the mouse to work.

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