Install Windows 98 SE in Parallels Desktop 3.0 for Mac

November 3rd, 2007

This is a how to guide for installing Windows 98 SE as a virtual machine in Parallels Desktop 3.0 for Mac. It was created using Mac OS 10.4.10, Parallels Desktop 3.0 Build 5160 and a bootable Windows 98SE CDROM.

Windows 98 Second Edition is an old, unstable OS that is no longer supported by Microsoft. Nevertheless, I had a need to install it because I have some older applications that I would like to run, which only run correctly on Win98SE, and not on Windows XP.

When installing Win98SE as a virtual machine, there are many obvious steps and a few not so obvious steps. This guide will take you through all of the steps, but will spend less time on the more obvious ones, and more time on the less obvious ones.

Here are the steps to the installation (the not so obvious steps are in red):

  1. Create the virtual machine.
  2. First boot/setup of Windows 98SE from CDROM.
  3. Change the boot order for subsequent boot-ups.
  4. Second boot/setup of Win98SE from CDROM.
  5. Subsequent boots/setup from Hard Disk and completion of Win98SE Install.
  6. Installation of Parallels Tools
  7. Manual Installation of Sound Driver.
  8. Get Windows Update to work by first installing IE6, SP1.
  9. Install Printer.
  10. Share Filesystem.

Create the Virtual Machine

  1. Start Parallels
    1. With Finder: Applications->Parallels->Parallels Desktop
  2. Create Windows 98 Virtual Machine
    1. Parallels Menu: File->New
    2. OS Installation Window: Choose “Typical”
    3. Typical Installation Window: Choose OS Type: Windows, OS Version: Windows 98
    4. Specify Name for Virtual Machine: Enter in what you would like to call the virtual machine (I used “Microsoft Windows 98 Test” as the name of my machine)
    5. Optimize Screen: I chose to optimize for better performance of virtual machine
    6. Insert Windows 98 CD, and click Finish
      1. (Optional) You can use a disk image (.dmg) file if you have one, instead of the actual Windows 98 CD. Expand the “More Options” on this screen in order to specify the CDROM .dmg file.

First boot/setup of Windows 98SE from CDROM

After clicking Finish on the last step, the virtual machine boots up from the CDROM. Here is what is to be done:

  1. Boot Menu: Choose (quickly because of timeout) “2. Boot from CDROM”.
  2. Microsoft Windows 98 Startup Menu: Choose “1. Start Windows 98 Setup from CD-ROM”
  3. You’ll now go through a series of screens (1, 2, 3, and possibly others that I didn’t screen capture) to choose various options until you are finally get a screen saying that “Setup will restart your computer now”. It says that you should make sure the Windows 98 boot disk is in drive A, but all that is really necessary is that your CD (or CD image) is there. Press ENTER to restart.
  4. After you press ENTER to restart, you will see a message from parallels that says “There is no operating system installed in the virtual machine”. This is expected right now and is not a problem. Click “OK”.
  5. Now, click the red square in the upper right corner of the Parallels window to stop the virtual machine. When you click it, parallels will ask “The virtual machine is running … Are you sure you want to proceed?”, click “Yes”.
  6. Do not restart the virtual machine yet. You must first change the boot order. Proceed to the next section of this guide.

Change the boot order for subsequent boot-ups

The next step of the Windows 98 installation requires you to boot from CD-ROM again. However, if you don’t change the boot order, the virtual machine will not be able to boot from the CD-ROM. If you try to boot now without changing the boot order, you will get a message from Parallels which states “There is no operating system installed on the virtual machine.”. If you click OK on that screen, you’ll see a message in the DOS-like window of the virtual machine which states “No boot device available, press ENTER to continue”.

You can only change the boot order when the virtual machine is not running. This is why it is stated in the last step of the previous section of this guide to not restart your virtual machine yet.

Here are the steps to change the boot order:

  1. Parallels Menu: Edit->Virtual Machine
  2. In the “Configuration Editor” window, Choose “Options” on the left side, and choose “Booting” on the top right side in the middle.
  3. Under boot sequence, choose: “CD-ROM, Hard Disk, Floppy”, and press OK.

The boot order is now changed, you can proceed to the next section, and it should work.

Second boot/setup of Win98SE from CDROM

After changing the boot order, you are now ready to perform the second boot up from CD-ROM for the Windows 98 installation. Follow these steps:

  1. Start the virtual machine by pressing the green triangle “play” button in the upper right corner of the parallels window.
  2. You’ll now see the boot menu: Choose (quickly because of timeout) “2. Boot from CDROM”.
    • This is the last time in this guide that you need to boot from CDROM. All subsequent boots will be from the hard disk.
  3. Microsoft Windows 98 Startup Menu: Choose “1. Start Windows 98 Setup from CD-ROM”
  4. You’ll now go through many screens that are part of the normal installation of Windows 98. Many files are going to get copied off of the CD-ROM, and this step could take 30-60 minutes. Here is a sampling of a few of the screens that you will encounter: 1, 2, 3, 4, 5
  5. Eventually you will be asked to reboot. Go to the next section of the guide for that.

Subsequent boots/setup from Hard Disk and completion of Win98SE Install

All reboots of the virtual machine from now on should be from the hard disk, and not from the CDROM anymore. To make things easier for yourself, you can change the boot order (Edit->Virtual Machine) to boot from the hard disk first, but this isn’t completely necessary. If you happen to boot off the CDROM and you get the boot menu, choose “1. Boot from Hard Disk” (or let it time out to boot from the hard disk).

There is a good chance that when you boot for the first time from the hard disk that you might be asked if you want to boot into “Safe Mode” with this screen. Do not boot into safe mode. Choose normal mode (Option 1), and choose it before it times out to boot into safe mode.

Even though you are booting from the hard disk from now on, you need to keep the Windows 98 CD (or image) in the drive so that setup can copy more files from it.

Complete the Windows 98 Setup by going through the setup screens. Expect to enter in your name and company, accept the license agreement, enter in your product key, etc. The setup will then say it is “setting up hardware and finalizing settings” and it gives an estimated time remaining. Eventually, it will ask you to set the time for the machine. It will then reboot, ask you for your name/password, find some hardware and install drivers.

When the “Welcome to Windows 98 screen” comes up, you are done with the Windows 98 install.

You are now ready to move on to the next section of the guide.

Installation of Parallels Tools

In order for Windows 98 to work properly under parallels, you need to install the Parallels tools. Follow these steps:

  1. Make sure the virtual machine is started and Windows 98 is fully booted up.
  2. Parallels Menu: Actions->Install Parallels Tools
    • Note: RealUnimportant has reported in his comment that the “Install Parallels Tools” option was greyed out when he tried to install the Parallels Tools. This wasn’t the case when I installed Windows 98, but if this happens to you as well, please read his comment to see how he fixed it.
  3. You will now get a message from Parallels about installing the Parallels tools, click OK.
  4. In Parallels Tools Setup Window, click “Next>”.
  5. Destination Location Window: leave the default and just click “Next>”
  6. Setup Type Window: Choose “Complete” and click “Next>”
  7. Ready to Install Window: Click “Install”
  8. The installation will copy files to the virtual machine.
  9. Installation Completed Window”: Click “Restart”. The virtual machine will now reboot.

Manual Installation of Sound Driver

For some reason, the sound driver is not installed with the Parallels tools. The Parallels User Guide has a chapter for describing how to install the sound driver on Win98. When going through these steps myself (with the user guide dated October 2, 2007), I experienced some small differences in the process from what is documented in the Parallels User Guide. Here is the guide for what to do based on my experience 1.

  1. Make sure the virtual machine is started and Windows 98 is fully booted up.
  2. Open the Control Panel. To do this, click the Start button, select Settings, and then Control Panel.
  3. Double-click the System icon to open the System Properties window. In the System Properties window select the Device Manager tab.
  4. Locate the PCI Multimedia Audio Device in the hardware list. Select it and click the Properties button.
  5. In the PCI Multimedia Audio Device Properties window click the Reinstall Driver button.
  6. In the first Update Device Driver wizard window, where it says “This wizard searches for updated device drivers for “, click “Next>”
  7. In the 2nd wizard window, choose “Display a list of drivers in a specific location…” and click “Next>”.
  8. In the 3rd wizard window, choose “Sound, video and game controllers” and click “Next>”.
  9. In the 4th wizard window, click the “Have Disk” button.
  10. The Install From Disk window is opened, in the Copy manufacturer’s file from: field, type the following path “C:\Program Files\Parallels\Parallels Tools\Sound” and click OK.
  11. In the Select Device window select one of the “Avance AC’97 Audio for Intel(R) Audio Controller [ 9-10-2007]” and click OK.
  12. In the next wizard window which says “Windows driver file search for the device…”, click “Next>”.
  13. If the wizard asks, insert the disc (or connect the CD-ROM image file) with your Win98 installation files and type the path to it in the field Copy files from. Click OK.
  14. After the wizard finishes copying files and you see this window, click Finish.
  15. Close the windows with AC’97 audio properties and system properties.
  16. Reboot the virtual machine (Start menu->Shutdown) for the new settings to take effect.
  17. When you do reboot, sound should be working and you should hear the bootup sounds.

Get Windows Update to work by first installing IE6, SP1

Even though Microsoft no longer supports Win98, it still allows you to download all of the critical security updates (and some other updates) that were available until the time MS stopped supporting Win98. It is a good idea to perform these updates.

If you try doing Windows Update at this point of the installation from this guide, it will not work.

In order to get Windows Update to work, you need to update to Internet Explorer 6, SP1. This can be downloaded and installed from here.

Now there are 2 different ways you can connect to the internet for the first time through IE6. The first method, which I documented below, is to execute IE6 and do a fake modem setup. RealUnimportant has noted in his comment however that the fake modem setup is not required, and his comment gives another method for how to do it. The fake modem setup is how I did it, and it worked for me, but sounds like there may be a better way – but I never tried this method.

After you have installed IE6, start Internet Explorer.

Unfortunately, you won’t be directly connected to your network connection here. You will get a screen that says Welcome to MSN Internet Access. I found that if you just go through these screens and tell it to install a modem, even though there is no modem there, you will be able to get to the internet with IE later on. Here are the steps that I went through in order to get this to work:

  1. Welcome to MSN Internet Access” screen: click “Next>”.
  2. Install New Modem window: Check the “Don’t detect my modem, I will select it from a list”, and click “Next>”.
  3. In the next window, you need to pick any random modem. I happened to choose the Manufacturer: 3com, Model: U.S. Robotics 33.6K FAX EXT. After choosing this modem, click “Next>”.
  4. In the window asking you to select a port: Choose “LPT1:”, and click “Next>”.
  5. Using your modem to connect” screen, click on “Lan/Manual”
  6. Setup your Internet Connection screen: Select “Connect using my local area network”, and click “Next>”.
  7. Local area network internet configuration screen: uncheck all boxes and click “Next>”.
  8. Set Up Your Internet Mail Account window: Select “No”, and click “Next>”.
  9. Complete Configuration window: click “Finish”

Now, test that when you run Internet Explorer, you will get to the internet. If you are getting to the internet now, you are ready to run Windows Update.

To run Windows Update, do Start->Windows Update. Follow the screens from there to perform the updates. Note that even after you install some updates, you should keep checking after each reboot for new updates because some of the updates are dependent on other updates to be there first. You may need to reboot and recheck for updates many times. You’re done installing updates when you check for new updates and no new critical ones are listed anymore.

Install Printer

The Parallels User Guide states that no matter what printer you really have on the Mac, you can install either an “HP Color LaserJet 8500 PS” or “Apple Color LW 12/660 PS” printer driver in the virtual machine, and you will be able to print.

The HP printer is not available in Windows 98, but the Apple printer is. I installed that and tried to print. It appeared that the print job got onto the queue in the Mac when I did that, but nothing came out of my printer. In my situation though, my printer is not actually connected to my Mac, but is accessed over my local network via another machine (running XP) that is directly connected to the printer. Maybe this has something to do with why the printing didn’t work, I don’t know.

In order to get printing to work for me then, I just installed a network printer on Windows 98. I am able to print from it now, but initial access over the network is slow.

Sharing the filesystem

Parallels Shared Folders isn’t supported for Windows 98. Therefore, you need to use standard Windows network file sharing techniques in order to share your files between W98 and the host OS.

RealUnimportant was kind enough to post his notes in his comment for some of the aspects of sharing the folders from Win98 with your Mac. I paste his notes below, thanks so much RealUnimportant!

Lastly, for explicitness for those who don’t see their Parallels machines whein they try to browse their mac’s Network folder: after using the Win98 File and Printer Sharing dialogues to enable file sharing and activate sharing on a folder/drive, go to Finder and select Go – Connect Server (cmd-K). Input the server address as smb://{vmname} and then authenticate using your guestOS username and password and there you have it, fileswapping capability. I’ve found that sometimes it doesn’t like me drag/dropping into this folder, if that happens to you try copy/pasting instead.


Windows 98 Thread on Parallels Support Forum

Parallels Desktop User Guide


1 The text for the sound driver steps has been copied and adapted from the Parallels User Guide, dated Oct 2, 2007.


June 1, 2008: Updated to take into account the excellent comment of RealUnimportant


  1. jbhon 05 Nov 2007 at 3:01 pm

    Not too different from mine, but I’ve been waiting to upgrade to Leopard before I check to see if any revision are needed.

    Also, when trying to install from an upgrade CD of Windows 98, many users had significant problems getting the CD to boot under Parallels. Here is a work-around for that.

    The screen shots are very helpful. Unfortunately the Parallels Forum restricts images to 4 per post, and each post must be less than 10,000 characters long. This forced me to economize on some of the details in my posts.

  2. jbhon 05 Nov 2007 at 3:20 pm

    For the adventurous, here is a hack to access a Parallels Shared Folder from a Windows 98 virtual machine. Personally, I get along just fine using the standard Windows file sharing mentioned above.

  3. formosaon 09 Nov 2007 at 12:48 pm

    I had huge problems with Parallels despite the great tutorial here, it would disable the cd so not be able to install drivers.

    I just tried Fusion and not only is it much much faster, it installed Win 98 no problem.

  4. Robon 09 Nov 2007 at 1:37 pm

    Formosa: I never had that type of issue with the CD that you had. Maybe the later versions of Parallels fixed the problem? Maybe using a CD image would have worked better than the actual CD. I haven’t tried VMWare Fusion, so I don’t have any opinion about it.

  5. danielon 03 Dec 2007 at 2:04 am

    Excellent write up very useful. I would appreciate more information on setting up windows file sharing with Windows 98. It is a cake with Windows 2000/XP & Vista but for some reason I can’t get it working with 98. It doesn’t provide me with a user name option so I created a new user in 98 that has the same user name as on my Mac. I still can’t connect. It always just says that the password is invalid.

  6. anonymouson 06 Dec 2007 at 12:14 pm

    It doesn’t appear that the video driver is working properly for win98. I don’t get any mouse synchronization (I can’t move my mouse out of windows back onto my mac desktop without hitting ctrl-alt). Also, I can’t resize the vm window and have win98’s resolution changed to fit that window.

  7. Robon 06 Dec 2007 at 12:49 pm

    Unfortunately, Parallels doesn’t have mouse synchronization for Windows 98. You must press ctrl-alt to get the mouse out of the VM window, that’s just the way it is. It also doesn’t support just resizing the VM window and changing win98’s resolution – that doesn’t mean your video driver isn’t working. To change Win98’s resolution, you need to right click on the Win98 Desktop and click “Settings”. If when you click the Settings you are able to move the slider to get different screen resolutions, then the video driver is indeed working correctly.

  8. billyon 21 Dec 2007 at 11:37 pm

    Thank you!! I was lost trying to get this to install windows 98. After hours of trying and reading the official forum, I came across your site. The second startup, boot order was the ticket. I wish parallels would simply add that step somewhere on their FAQ section. Again thank you and cheers!!!

  9. Jon Don 03 Feb 2008 at 1:12 pm

    I’ve tried to set up a shared network printer in 98SE VM and all of my settings on my Leopard OS seems to be correct. The 98 VM sees the Mac computer but not the printer. This is my first ever attempt to set up a shared network and I’m sure its probably improper settings issue in the 98 VM. Sure could use some help!

  10. Damien Buckleyon 03 Feb 2008 at 8:38 pm

    Thanks for this hugely helpful (and comprehensive) guide Rob- I’m a first time Parallels user and was pulling my hair out with win98 – I want to keep IE6 running in 98′ and IE7+ in XP (rather than mess too much with multi-IE etc)and this guide is an absolute godsend. Thankyou

  11. steveon 15 Feb 2008 at 5:09 pm

    Sorry to ask questions here, but any idea why, after following all your steps, I cannot access internet in Win98? When MSN setup asks me to select a port, there are none where the list should be…

  12. Steveon 18 Feb 2008 at 12:51 pm

    Well, it seems to be something to do with Leopard. Works fine on OS X 10.4

  13. Richard Wardon 05 Mar 2008 at 10:27 pm

    I love how no matter how fast your Mac is, fdisk, the installer, etc. still take forever to run just like it did a decade ago when we all ran the latest version of Microsoft’s OS: Windows 98 SE.

    What a flashback.

  14. arielon 19 Apr 2008 at 12:27 pm

    perfect guide!
    very good!

  15. Willon 13 May 2008 at 3:20 am

    Many thanks for preparing this excellent guide. I’ve just got a new 3Ghz iMac and purchased Parallels as part of the MacUpdate bundle. But the only OS install disk I could find was for Windows 98. So this and Ubuntu is what I’ve started with so far until I can get an XP disk for running Parallels properly.

  16. yoinkon 21 May 2008 at 6:36 pm

    Works perfectly in Leopard on my BlackBook 2.4 GHz. I couldn’t figure out how to install the sound driver, so thank you very much for preparing me for countless hours of retrogaming ahead 🙂 Excellent work!

  17. RealUnimportanton 01 Jun 2008 at 4:45 am

    A couple of amendments I’ve thought of while working through this otherwise sterling guide:

    Firstly, while my Win98.iso file was connected to the VM, Install Parallel Tools was greyed out. The Parallel Tools .iso is located in /Library/Parallels/Tools, connect it manually and it’ll ungrey in the menu. This still didn’t let me install it however, clicking the menu option did nothing, so I just opened the CD in the guestOS manually and it autoplayed and installed perfectly.

    Also, you don’t need to go into the Control Panel when looking for the Device Manager; just right (ctrl) click the My Computer icon and select Properties, and this takes you sraight to the System Properties screen.

    You don’t need to go through the fake modem selection process if you follow the instructions given in the official 98SE guide for going online – just click the Connect to the Internet icon instead of IE, and tell it straight away that you’re trying to connect through a LAN.

    Lastly, for explicitness for those who don’t see their Parallels machines whein they try to browse their mac’s Network folder: after using the Win98 File and Printer Sharing dialogues to enable file sharing and activate sharing on a folder/drive, go to Finder and select Go – Connect Server (cmd-K). Input the server address as smb://{vmname} and then authenticate using your guestOS username and password and there you have it, fileswapping capability. I’ve found that sometimes it doesn’t like me drag/dropping into this folder, if that happens to you try copy/pasting instead.

    Regardless of this nitpicking, I found this guide to be much easier to follow than the official one, and I now have a working Win98 machine for the first time in 6 years 😀 Oh, and while you may consider it “unstable”, I once had it running on a live machine for up to 6 weeks between reboots, and it was in daily use as a gaming/surfing machine… I put this success down to never installing any other MS retail software 😉

  18. Robon 01 Jun 2008 at 7:05 pm

    Thanks for your detailed comment RealUnimportant.

    I didn’t know about the method you have for connecting to the internet instead of the fake modem setup that I did. I will add that to the guide.

    I didn’t seem to have the issue that you had with the Install Parallels Tools greyed out, but your notes should be helpful for those who do have that issue so thanks for writing about it. I will also add this to the guide.

  19. Michaelon 27 Aug 2008 at 12:36 am

    Ahhhh, the installation went beautifully well, thanks. However, I have a PCI Bridge and PCI Universal Serial Bus that is not functional – the drivers are missing. Also, APM support is missing. Any ideas as to what to do to correct these last three items. I see that someone else had the same issues on the Parallels Support Forums. No Fix or Solution provided there either. Also, the Virtual 98SE System just went to sleep and crashed. Reset was successful. Now set for No Display Sleep!!! Any input? Thanks!

    So, where does one find the actual specs for the base platform that is actually running under the Parallels VM? A particular Main Board and Chip Set emulation? Anyone?

  20. Wimon 28 Sep 2008 at 7:24 am

    Hi, thanks for this excellent manual. It helped me a lot.
    About sharing this: you can stop VM and then mount the win98 HD (double click on the HD image). From that point you’re able to reach all the directories you want.
    Not a nice, but effective solution for some people.

  21. wad11656on 04 Mar 2009 at 10:45 pm

    Could you make a modified guide for Parallels 4.0? I believe you’d just be able to copy & paste all your instructions for here EXCEPT for all of the drivers. It would be wonderful to know how to get the sound working on my Windows 98 SE.

    Also, the same thing happens to me when trying to set up a printer with a local connection–it only appears in the printer queue, and the printer even warms up and gets ready, but it doesn’t print. How exactly did you set up your Network connection for the printer? It prompts for the “Network Path or Queue name,” but I have no idea what that is. When I click “Browse…” I don’t see anything, so I try to expand “Entire Network,” but it says “Unable to browse the network. The network is inaccessible”…etc.

    So I just need a step-by-step explanation on installing the Sound driver and the printer set-up. Thanks!


  22. wad11656on 04 Mar 2009 at 10:47 pm

    QUOTE by RealUnimportant: “Input the server address as smb://{vmname} and then authenticate using your guestOS username and password and there you have it, fileswapping capability.”

    Um…What do you mean by “{vmname}”? Like i.e. “Windows 98.pvm”, “{Windows 98.pvm}”, “Windows 98”, “{Windows 98}”, or what?

    It’d be nice to be able to file swap, so please enlighten me. Thanks!

  23. peteron 06 Aug 2009 at 6:19 am

    After installing Parallels Tools my windows 98 refuses to shut down properly. I receive a black window and I have to end Windows 98 by pressing the little red block. Starting up again, it takes a long time because it was not finished (it must scan everything) in the correct way.
    Thanks for possible suggestions, and Thanks for all information on this forum!

  24. andron 19 Jan 2010 at 2:43 am

    I spent hours trying to install Windows 98 with Parallels 4: Forget it! It’s no problem with Vmware Fusion. Fusion rocks.

  25. kimon 17 Mar 2010 at 10:01 pm

    ?? ?? ? ?? G3 ??

    ??? 98 ???? ?? ? ?????

  26. Niclas Engströmon 10 Apr 2010 at 5:23 am

    My stupid stupid parallels changes the name of and add (1) => Windows XP…..(1)(1)(1)(1)(1)(1)(1)(1)(1)(1) in the name of the virtual machine????? WHY is that and how do I make it stop.

  27. Nickon 12 May 2010 at 2:19 pm

    I have been trying to install Parallels Tools on my Win 98.
    I got to sent the prl-tools-win.iso by Internet and let it explode in Win.
    Unfortunately I get an error message.
    I can send the image of it.

    Someone can help me?



  28. Kojejeon 17 Jul 2010 at 1:43 am

    Oww, I just found this site 🙂
    Cool…! Keep posting 🙂

  29. Mikeon 15 Feb 2011 at 1:20 pm

    Great tutorial, saved me a lot of grief when trying to install 98. Cheers mate.

  30. Jason Andersonon 12 Apr 2011 at 3:24 pm

    Sadly the Tools won’t work for me. If I connect the ISO manually and try to run the Autorun, it tells me “Needs Windows 2000 or higher”. Where can I get Windows 98 versions of the tools? And would they fix my display problem of only being able to use a slow refreshing 640×480 16 color screen?

  31. Lalit Ramsisariaon 08 May 2011 at 5:04 am

    I too am having many problems post installation. I am unable to install parallel tools. I have tried all the ways provided. And I am also unable to see mac files in the network neighborhood. Is it because I am using Parallels v 6.0 ? Please help. Thanks in advance.

  32. Davidon 23 Sep 2011 at 10:29 am

    @ Jason Anderson Use the “prl-tools-other.iso”.

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