Running a Windows 3.1 VM in Virtualbox

  1. Download MS-DOS 6.22 Download
  2. Download Microsoft Windows 3.1 Download
  3. Extract the MS-DOS 6.22 and Windows 3.1 files
  4. Launch Virtualbox
  5. Create a New VM by selecting Machine > New

    Name: Microsoft Windows 3.1
    Machine Folder: C:\VMs
    Type: Microsoft Windows
    Version: Windows 3.1
    Memory Size: 256 MB
    Hard disk: Create a virtual hard disk now

  6. Click Create
  7. On the Create Virtual Hard Disk dialog

    Name the virtual disk image Microsoft Windows 3.1.vdi
    File size: 1 GB
    Hard disk file type: VDI
    Storage on physical hard disk: Dynamically Allocated

  8. Click Create
  9. Select the VM and Click Settings
  10. Select Storage
  11. Click on the floppy disk drive
  12. Select the disc dropdown to the right > Choose a virtual floppy disk file...
  13. Browse to the extracted MS-DOS 6.22 files and select Disk1.img
  14. Click OK
  15. Make sure the Windows 3.1 VM is selected and click Start > Normal
  16. Press Enter to start the installation and press Enter multiple times to accept the default values
  17. When prompted by the installer, go to the VM settings and swap out the MS-DOS disk images and press Enter to continue
  18. Once MS-DOS has been successfully installed, select Devices > Floppy Drives > Choose disk image...
  19. Navigate to the extracted Windows 3.1 files and select DISK1.img
  20. Press Enter in the VM
  21. Once MS-DOS has booted, type the following commands
    A:
    setup
  22. The Windows 3.1 installation process will start
  23. Press Enter to continue
  24. Press Enter to begin the installation
  25. When prompted by the installer, go to the VM settings and swap out the Window 3.1 disk images and press Enter to continue
  26. When prompted, enter a name and click Continue
  27. Click Continue to confirm the name
  28. Click Cancel on the Printer Installation dialog
  29. Click OK on the Setup Applications dialog
  30. Click Skip Tutorial
  31. Select Devices > Floppy Drives > Remove disk from virtual drive
  32. Click Reboot
  33. Once MS-DOS has booted, type the following commands
    win
  34. Welcome back to Windows 3.1
  35. Launch Accessories > Notepad
  36. Select File > Open
  37. Navigate to the root of the C: drive and open autoexec.bat to edit it
  38. Add win to the bottom of the file to automatically boot Windows 3.1 on system startup
  39. Select File > Save
  40. Select Machine > Reset > Reset
  41. Revel in the nostalgia