Installation of Windows 98SE using VMware Player

Introduction

The Windows 98SE Operating System Reached End of Life on the 11th of July 2006.

This guide will instruct on installing Windows 98SE in VMWare Player Workstation 15.2.

Video

Install VMWare Workstation Player on a Windows 10 64 Bit Host:

The website WinWorld has a Windows 98SE ISO with a Generic Serial Key on the Right Hand Side of their Website. Ensure you download the OEM Full 544.44MB ISO as it is the only one that is Bootable.

Install 7zip and use it to extract the ISO:

You will also need the following update packages and system drivers:

Setup VMware Player

Select Player → File → New Virtual Machine:

Select Browse, load your Windows 98 SE ISO. You should get a balloon stating that Windows 98 SE is detected. Select Nect:

You will be given a default value for your VM name and location. I will add SE to the end of the default name. When done select Next:

Change the size to 20 GB:

Select customise hardware:

Under Memory move the slider up to 1 GB:

Select Network Adaptor and make sure Connect at Power On is unchecked (we do not want to give an OS that hasn't had security updates for 15 years internet connectivity).

Select USB Controller and change USB Compatibility to 1.1. VMware Tools do not have a USB 2.0 or 3.0 driver for Windows 98 SE. Once you've made the changes select Close,

Select Finish:

Installing Windows 98SE

Select the Play Button to Start the VM:

VMware will also tell you the magic keyboard shortcut keys. [Ctrl] + [g] to take your mouse to the VM:

And [Ctrl] + [Alt] to take your mouse away from the VM.

Press [↓] and select Boot from CD-ROM and press [Enter]:

Select Remind me later if you get a prompt for VMware Tools:

Select Start Windows 98 Setup from CD-ROM:

Press [Enter]:

Select "Configure Unallocated Space" and press [Enter]:

Press the [↓] key and select "Yes Enable "Large" Disk Support" and press [Enter]. This is still tiny by todays standards:

Ignore any mention of the floppy drive A: and press [Enter]:

Your VM will restart, you will see the Legacy BIOS splash screen:

Once again press the [↓] key and highlight Boot from CD-ROM. Then press [Enter]:

Select the first option and press [Enter]:

Windows 98SE will then format the virtual hard disk:

Press [Enter]:

Select [Continue]:

Use the default directory and press [Enter]:

Select Typical and press [Next]:

Select the Recommended Option and press Next:

Type in your Computer's name and press Next:

Select your Country and select Next:

Select Next:

Your Windows 98SE VM will restart:

You will see the Virtual Legacy BIOS Splash screen and Windows 98SE logo:

Input the generic Product Key and select Next. There was no product activation with Windows 98SE as many users never had an internet connection:

Select Finish:

The setup will configure on the Virtual Hardware:

The VM will restart, you will see the Windows 98 splash screen followed by the Virtual Legacy BIOS splash screen followed by the Windows 98 splash screen:

Windows 98SE will setup hardware:

Select your time zone and select Apply:

Then select OK:

The System Settings will Update and the Windows 98 VM will once again restart:

You" once again see the Windows 98 splash screen, the Virtual Legacy BIOS splash screen and the Windows 98 splash screen again:

Select OK to log in:

Windows 98SE will Add New Found Hardware:

It will Update the System Settings again:

You will see the Welcome to Windows 98 splash screen. Uncheck "Show this screen every time Windows 98 starts" and select Close:

Installation of VMWare Tools

Select Player → Manage → Install VMWare Tools:

You will be prompted to Download and Install VMware tools (note the download will come via your host PC and not via your guest PC).

The tools will download:

You will get a message about the CD-ROM Drive. Select Yes

The VMware Tools will extract:

Select Next:

Select Next:

Select Install:

Select Yes:

Select Finish:

Select OK:

Select Finish:

Select Yes to restart:

You will see the Windows 98 splash screen, the Virtual Legacy BIOS splash screen and the Windows 98 splash screen again:

Select OK to log in:

You can now resize the VM however the first time you do this, it won't resize.

Right click the Desktop and select Properties:

Now select Settings and change the slider to the maximum position:

Select Apply and then OK:

Now the screen will be too big, but select Yes anyway:

When you resize the Window, the VM will now resize with it. Select cancel at display properties:

That's you got VMware tools installed:

Installing Updates

You should now be able to drag and drop the Unofficial Service Pack U98sesp3 to the VM:

Double click it and select Yes:

It will extract:

You can close the information:

Check Main Updates/System Core Files (Install Separately) only and then select OK:

When done select OK and restart as prompted.

Relaunch the U98sesp3 and then select Microsoft DirectX 9.0c End-User Runtime (Install Seperately) and then select OK:

Restart when prompted. Relaunch U98sesp3 and select Universal Plug-n-Play 4.90.3003.0

You can optional install anything else here.

Installing System Drivers

Right click Computer and Select Properties:

Select Device Manager. You should have two unknown Devices:

  • PCI Multimedia Device → Soundblaster PCI128
  • PCI System Peripheral → This is the VMCI and VMWare has no Windows 98SE driver

If there is also:

  • PCI USB (You have USB2.0 or USB3.0 settings, which are not supported in Windows 98SE, change your VM Settings to have USB 1.1)

Drag SBPCI_WebDrvsV5_12_01 over to your VM and install:

Select OK to proceed with the install:

Select No when you get the Version Conflict warnings.

Your Device Manager should look as follows.

It is recommended to install the Logitech Mouse Driver.

Addition of Legacy Devices

You can add more hardware such as a floppy drive (virtual floppy drive with .flp images or an onboard/USB floppy drive), serial port (onboard or USB serial port) and parallel port (onboard or USB serial port). Power off the VM and right click your VM and select settings:

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Select Add Hardware:

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Select yes at the User Account Control:

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You may add a floppy drive, parallel port and/or serial port depending on the legacy hardware you wish to connect to:

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I advise not setting the Floppy to Connect at Power on otherwise the system will try to boot from the Floppy Disk before the HDD> This can be amended in the BIOS setup however:

floppy
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These and USB devices can be accessed via the Player Menu. Each optical drive, floppy drive, network adapter, serial port, parallel port and soundcard will be listed separately. Below these any USB device are listed. If the USB devices have a tick they are connected to the VM (and removed from the Host OS). The Ability to connect to all of these Removable Devices and the installation of legacy Windows OS make the VM very powerful:

vmdevices

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