Upgrading to Windows XP from Windows 9x/Me

The vast majority of people who upgrade to Windows XP will take an existing Windows 98, 98 SE, or Millennium Edition (Me) installation and ...

Paul Thurrott

October 6, 2010

12 Min Read
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The vast majority of people who upgrade to Windows XP will take an existing Windows 98, 98 SE, or Millennium Edition (Me) installation and upgrade it in-place. However, this upgrade isn't without pitfalls. Windows 9x/Me and XP may look similar, but they're built on two completely different technology platforms, and it's actually sort of amazing that an upgrade between them can take place at all. Windows 9x/Me is based on DOS, a 16-bit command line OS that debuted in 1983. XP, however, is based on the stable and reliable 32-bit NT platform, which first debuted in 1993. It is the technological successor to Windows 2000, not Windows 9x/Me.

So why is such an upgrade even possible? Well, Microsoft has been working for almost a decade at melding its consumer-oriented 9x line with NT. The first step occurred before NT was even released, when Microsoft decided to give NT the Windows 3.x user interface, making it easier for users to move from one platform to the next. However, in the early days of NT, compatibility was a nightmare: NT could run some DOS and Windows applications (albeit slowly), but it could work with only a small subset of the hardware that was available to DOS/Windows users.

In 1995, Windows 95 became the first DOS/Windows release to feature NT technologies, in the form of the Win32 API, which programmers use to create 32-bit Windows programs. The version of Win32 in Windows 95 was actually a bit different than that used by NT, but it was a start. Future NT releases, such as NT 4.0 and 2000, closed the gap, and 2000 added a lot of important 9x features like Plug-and-Play support, hardware-accelerated DirectX support, and the like. And later 9x releases, especially Windows Me, incorporated some reliability and stability technologies, though the inherent instability of the underlying platform undermined much of that work.

But over the past five years or so, the 9x and NT lines have been converging. In Windows 2000, Microsoft finally made it possible to upgrade 98 machines to an NT-based product, though the company only supported business oriented applications and hardware. Finally, in XP, it's possible to take Windows 98 (or newer) and upgrade it to a modern, reliable OS, one that can stay running day after day. And most of your applications, games, and hardware will actually work too. It's sort of amazing.

How they did it
Upgrading Windows 9x/Me to Windows XP is actually a bit of a misnomer. When you upgrade such a system, Microsoft actually examines your installation, moves your documents and personalized settings to a backup location, and then performs a clean install of XP. Then, it goes back and applies those personalized settings to the new OS and moves your documents into the correct location (My Documents, which is located in a different place in XP than it was in 9x/Me). This is why it requires so much free space for the upgrade, by the way.

Also, by default, XP Setup will backup your existing 9x system so you can uninstall XP and go back if you have problems. I strongly recommend allowing it to do so (you'd have to go out of your way to prevent it), because this gives you an out if anything goes wrong. And trust me, with a move between two very different technologies, something very well could go wrong.

However, there are other safeguards. During the upgrade, XP Setup will examine your current system and create a report explaining what types of problems you might have with hardware and software. A hardware device might not be supported under XP, for example, and require a new driver from the manufacturer. You might have to reinstall certain software, or may find that some software--especially virus scanners, disk utilities, and the like--will not work at all under XP. If you want to run this test before installing (or even purchasing) XP, please read part two of this Installation Super Guide, Using the Upgrade Advisor, first. This tool will provide you with the same information as XP Setup, giving you time to collect the necessary updates ahead of time.

Also, there is tremendous application compatibility software running behind the scenes in XP. Described in my showcase titled Windows XP Hardware and Software Compatibility, this software can actually fake out thousands of popular DOS and Windows games and applications, and make them think they're running on Windows 95, 98, NT 4.0 or 2000. Using such software shims, XP makes it possible to seamlessly run older programs in a way that was impossible with Windows 2000. And if that still doesn't work, you can manually fake out recalcitrant apps by applying OS templates to shortcuts on the fly.

OK, you've been warned, but honestly, most people will experience a successful upgrade. I just wanted you to be aware of the work that was done behind the scenes to make it possible.

Pre-installation checklist
Before you install XP, there are just a couple of things to do.

1. Think before changing your file system - Windows XP supports the old FAT and FAT32 file systems from Windows 9x/Me, but it also supports the newer NTFS file system from NT/2000, which adds better security, support for encryption (Pro only) and some journaling features. If you are ever prompted to upgrade your file system to NTFS during Setup, remember that NTFS is incompatible with Windows 9x/Me. So if you need to dual boot with another Windows 9x install, you shouldn't use NTFS. And if you think there's any chance you're going to be uninstalling XP and going back to your previous OS, you will lose this option if you upgrade the file system. My advice, then, is to not upgrade the file system to NTFS during Setup.

You can always convert the file system to NTFS later, however. Windows XP includes a command line utility, convert.exe, that will convert a FAT or FAT32 drive to NTFS. Open a command line window and type convert /? for details.

2. Run scan disk and the disk defragmenter before upgrading. Upgrading to XP is going to cause a lot of damage to the structure of files on your system, so you might as well clean it first. You're going to want to defrag the disk after installation too, however, but you might as well get the hard disk off on the right foot.

3. Run the Upgrade Advisor and see whether you're going to need any updated drivers or software updates. If so, download them now and have them on the hard drive so you can install them after XP is installed.

OK, let's take the plunge and upgrade to XP.

Step-by-Step: Upgrading Windows 9x/Me to Windows XP
Upgrading Windows 9x/Me to Windows XP is a straightforward process. In the following example, a heavily used Windows 98 system is upgraded to Windows XP Professional, but the steps are identical for any 9x-based OS.

1. Insert the Windows XP CD-ROMWhen you insert the Windows XP CD-ROM, you will be confronted by the front-end application shown here. Select Install Windows XP to continue.

2. Close all applicationsIf Setup detects any applications running that will hinder the installation of XP, you'll see this warning now. Anti-virus utilities and other system-level applications are the most obvious problems.

3. Choose an installation typeWhen the Setup wizard begins, it will prompt you to choose between an upgrade and a clean install. An upgrade will take your existing operating system and upgrade it to Windows XP, and this is the option we will select here. You can choose clean install if you'd like to overwrite the existing OS or install XP in a dual-boot situation.

4. License agreement and product key Next, you'll have to agree to Microsoft's complex licensing agreement. Among the highlights: You don't actually own Windows XP and you can only install it on one PC. In the next step, you enter your product key, which is found on an orange sticker attached to the XP CD's jewel case.

5. Upgrade reportThis step duplicates the functionality of the Upgrade Advisor, which we discuss in part two of the XP Installation and Upgrade Super Guide. You should make note of any software or hardware issues that are found during this step.

6. Get updated Setup filesIf you're connected to the Internet, Setup will next ask you whether it can update itself over the Internet using the new Dynamic Updates technology. I strongly recommend you do this, as Microsoft will be updating XP Setup with new critical updates and driver additions over time, and this will ensure that your copy of XP is as up-to-date as possible when first installed.

7. Updating SetupAt this point, Setup is updated and some boot files are copied to the PC. Setup will then automatically reboot the computer. If you see a message about pressing any key to boot from the CD-ROM at this point, do not do so: Your PC has been configured to boot Setup off the hard drive.

8. Preparing SetupIn this phase of Setup, more files are copied to your computer in preparation for installation. Then, it will reboot again. As before, be sure to not hit any key if your PC prompts you to do so to boot off the CD-ROM.

9. Installing Windows In this Setup phase, Windows XP installs devices and the network, then copies and configures the other files needed to install XP. The Start Menu items are installed, and then components are registered.

10. Finalizing installation In the final phase of Setup, program and system settings are upgraded, settings are saved, and, finally, temporary files are removed. Then the system reboots again.

Post-upgrade tasks
Once Windows XP is installed, it's time to perform a few post-installation tasks:

1. Test installed software. Check to see that your software programs all work as before. If any do not, attempt to reinstall them using the original setup disks, or check the Web sites for the specific applications to see whether there are any updates. If any are still not working, open up Help and Support and navigate to the Fixing a problem link under Pick a Help Topic. There, you will find help about solving application and software problems.

2. Test installed hardware. Make sure all of your hardware works. Open up Device Manager (Open the Start menu, right-click My Computer, choose Properties, then go to the Hardware Tab and click Device Manager) and make sure all of your hardware was detected and has working drivers. If any do not--as evidenced by a yellow bang next to the hardware device's name, right-click and choose Update Driver. This will launch the Hardware Update Wizard. The first time around, ensure the XP CD-ROM is still in the drive, and try the option titled Install the software automatically (Recommended). If this doesn't work, visit the hardware maker's site and see if there is an updated XP-compatible driver. If this fails, open up Help and Support and navigate to the Fixing a problem link under Pick a Help Topic. There, you will find further help about solving hardware and system device problems.

3. Run Windows Update to make sure your system is up-to-date. Starting October 25, 2001, there will be many, many updates for Windows XP on this site, so you should visit Windows Update right away. You may need to reboot after certain updates, and some updates will require you to install them individually. Keep installing and rebooting until you've got them all.

4. Defrag your system drive. During an upgrade, your system drive is going to become heavily fragmented. To defragment this drive, open My Computer, right-click the drive (typically C:) and choose Properties. Navigate to the Tools tab and select Defragment Now.

5. Customize the system further. At this point, you might want to configure the wallpaper, screensaver, and other features, especially if these features weren't carried over from your previous Windows version for some reason. Windows XP configuration occurs in a number of places, but some hot-spots include:

Display Properties - Right-click an empty area of the background and choose Properties.

Performance options - Right-click My Computer, choose Properties, and navigate to the Advanced tab. Click the Settings button under Performance.

Control Panel - configure hardware, networking, installed applications, and other XP features.

Finally, use Windows XP for a few days and make sure that everything works properly. Once you're positive that all is well, you can go into Control Panel and then Add or Remove Programs and remove the option to revert to your old operating system. This could save a lot of disk space, but don't do this until you're sure you won't want to go back.

Where to go from here...
Hopefully, everything went well and you're all set. But remember that a 9x/Me to XP upgrade isn't the optimal way to move to XP, and if it's possible, I recommend going the clean install route. I'll explore that in a future showcase, but next up is the Windows NT/2000 upgrade to XP.

About the Author(s)

Paul Thurrott

Paul Thurrott is senior technical analyst for Windows IT Pro. He writes the SuperSite for Windows, a weekly editorial for Windows IT Pro UPDATE, and a daily Windows news and information newsletter called WinInfo Daily UPDATE.

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