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Virtualization, Windows 98, and Java - Oh My! 
Lots of folks just LOVE those old Microsoft Operating Systems. Be we looking to play a classic game, run a licensed application, or simply enjoy the ability to use Windows 98 and / or Windows 2000 much like we would any activation-free operating system, having the ability to "just boot it" is a refreshing experience.

Indeed, in as much as most folks with any tenure in the industry at-all have 8 to 10 classic Windows 98 / Windows 2000 licenses with keys, the fact that we are not even able to re-activate Win98 or Win2K over and over again ... is a real bonus!

So while doing a little testing for a book I have been researching, I decided to pop-in a '98 next to the '2K, 'XP and '7 in Oracle's Virtual Box.

Installing Windows 98

With something as old as Windows 98 (almost 15 years at the time of this writing!), one might expect a few "gotchas" along the way.

When creating your Windows 98 VM using Virtual Box, be sure to:

(1) Don't be afraid to use a lot of resources: Windows 98 can address 1.5GB of RAM, as well as a few gigs of disk - feel free to chew-up a little over 135GB on that virtual hard drive. Most folks find that 2GB is usually more than enough.

(2) Like any old software, do NOT let that hard-drive expand virtually! When creating the virtual drive therefore, be sure all disk is formatted & ready for use - just like we have to do when installing SQL Server!

(3) Be sure to enable linear, real-mode addressing!

To enable the supported "flat-mode addressing" in the VM, while creating the VM simply click on "Settings" then (a) select the "Processor" tab under "System" to "Enable PAE/NX", then (b) under the "Acceleration" tab, be sure to DISABLE VT-x/AMD-V (and yes, I was using an AMD chipset - the downgrade works fine.)

(4) While installing Windows 98SE (the recommended release -- available on eBay for about $10), feel free to click "Y"es on the two blue-screen message you may get if they are complaining about missing DLL's. This is a soft problem. Works fine afterward.

Installing Java

Java 5 is officially the last release to support Windows 95, Windows 98, Windows ME. If we can endure a single install-time warning however, Java 6 Update 7 ( was the last demonstrably working version. Use jre-6u1-windows-i586-p.exe after installing '95, '98, or 'ME.

Before installing Java however, note that unlike my EzInstall (which includes the installer & un-installer as part of the program itself), that in order to install anything created with Microsoft Installers, you need to first install ... uh ... the installer. For Win98, we will also need to download Microsoft Installer Version 2.0.

Browser Caveats

There are two:

Of course the browser is ancient. In modern terms (CSS, XML, HTML 5) Windows Explorer will not do a lot for you.

Indeed, when I first started the '98 browser, by default it would not allow me to browse anywhere without selecting a modem.

We can easily get around that problem by setting up a LAN to connect to the Internet before opening the browser the next time.

The second browser problem is the default home page. Since Windows 98 is no longer supported, the junk loaded at the default Microsoft site actually crashed the bowser!

To fix the problem, simply cancel the browser-fetch when you first start Internet Explorer, then set up the "use blank page" default under "Internet Options."

Virtual Box Caveats

Note that Oracle's Host Extensions will not work. The last of the 16 bit MS Operating Systems, one must get used to not being able to run 32 bit code. In as much as Win98 can boot MSDOS in real-mode however, folks with an interest in that DOS legacy can easily learn to live with the limitation.

Unfortunately, when we loose the ability to install Oracle's Host Extensions, we also loose the ability to share host-folders with a virtual machine. So while things like FTP, USB (if you can find a driver), ISO images, email, and CD-ROMS are viable data interchange options, note that the browser will allow us to pull things down just fine.

Support & Security

'95, '98, and 'ME are no longer supported. Don't even bother checking for updates (another bonus?) -After installing everything you need, consider disconnecting the VM from the Internet.

Why drop the 'Net? Because even if the VM is behind a firewall, there simply were TONS of back-doors and exploits (see the 'Bottom-line Benefits' section (below) for recovery information.)

By way of clarification, we should note that a down-to-earth (pun intended), home-spun, external-net-disabled LAN is great for game-play. Just remember: Less Internet, less attack surface.

(In a like manner, unless one lives well out-of-range, then be sure to button-down that wifi, too!)

Bottom-line Benefits

From an end-user point of view, certainly the greatest benefit of using virtualization is the ability to take snapshots, and export appliances. A snap-shot allows us to save an image before a potentially dangerous operation. If things go bump-in-the-core, we can quickly set the entire machine back to a last-stable snapshot. When restoring a snapshot, since the delta (restored change) comes from outside of the VM, even a newly-installed virus doesn't stand a chance of being a problem. (I use the snapshot feature a lot when installing, layering, and cross-upgrading software on Microsoft Servers!)

Exporting an appliance is also one great way to back things up. Unlike when using snap-shots, routinely exporting appliances will allow us to take our work with us (by importing the appliance to a laptop (etc.) "just like a book"), or recovering the entire (operating system + installed applications + our data) as part of an extremely robust disaster-recovery plan. --No safe deposit box should be without one.


After reviewing the above tome, I must admit that it all LOOKS a lot more involved than it is. Rather than being intimidated, just give it a try.

Enjoy the freedom!


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