Setup Guides

This page will contain links & documentation how to get started with a vintage operating system, most notably, by installing one in a retro PC emulator such as 86Box.

It is on my To Do list to write my own guides for these operating systems; in the mean time I will link to some resources I found below. For Windows 98, for now I host a copy here of a text tutorial I found on GitHub which was verified to work well.

Table of Contents

• Windows 3.1
  • With 86Box
  • With VirtualBox
  • With DOSBox
• Windows 98
  • With 86Box

Windows 3.1

With 86Box

86Box so far has been the best method I found to faithfully emulate a Windows 3.1 machine, since it deeply emulates the hardware (motherboard, CPU, BIOS, graphics card, etc.) and so works with the real driver software for those peripherals, runs the CPU at speeds accurate to the era, etc.

• YouTube: How to install Windows for Workgroups 3.11 in 86Box^https

  I followed this guide and got a perfectly working WfW 3.11 machine set up with Internet access and was able to develop & test this very website using Internet Explorer 5.0 and Netscape 3.4 from that machine!

With VirtualBox

Windows 3.1 can be installed in VirtualBox^https, though you may run into compatibility issues since virtual machines run the guest OS code on your real CPU (old games may run too fast on modern clock speeds) and virtual machines don’t deeply emulate hardware devices like 86Box does.

Some tutorials I found online (haven’t tested these recently):

• VirtualBox.org Tutorial: Installing Windows 3.11 with (working) drivers!^https

With DOSBox

DOSBox and DOSBox-X are DOS emulators most commonly used for playing vintage videogames. However, given that Windows 3.x was really just a program for MS-DOS, these emulators can be used to install a basically workable copy of Windows 3.x.

In my experience, Windows 3.1 works just okay in DOSBox: you can play graphical 16-bit games like Chip’s Challenge, but you will encounter some quirks and bugs that wouldn’t have been present on real hardware.

• Installing Microsoft Windows 3.1x in DOSBox-X^https

Windows 98

With 86Box

Hosted locally here:

• Install Windows 98 SE in 86Box

  This guide is a mirror of the one I found below on GitHub. I successfully followed this guide and got a good working Windows 98 machine with Internet access and video drivers all functional.

Hosted elsewhere:

• Text: Install Windows 98 SE in 86Box^https

  Text guide hosted on GitHub, which I mirrored above so you can read it locally here in case your web browser can’t read HTTPS sites.

• YouTube: How to install Windows 98 in 86Box^https

Page last updated on May 21, 2026