Triple-booting Windows 98, NT 4, and 2000

With my Dell Dimension XPS T450 ready hardware-wise, I needed to get some operating systems installed. My ideal setup is triple-booting Windows 98, NT Workstation 4, and 2000 Professional. This isn’t as straight forward as you’d imagine and it took me more than one total reformat to get it working. This is a tale of many, many failures finally leading to some success.

Start from scratch

To start, I did a low level format of my SCSI hard drive from within the Adaptec SCSI controller BIOS. This took a long time to do a 73 GB drive, but it ensured I was starting from scratch. I had tried re-initialising the disk with fdisk in a Linux live CD, but I ran into some issues with that.

My earlier attempts to get this setup working started with Linux where I partitioned the whole drive to get it ready for Windows installations. But Windows had various problems with this. I assume something wasn’t quite right with what Linux did, or it had set some FAT32 or NTFS attributes that didn’t exist back in the 90s. I don’t know.

Partitioning strategy

There are a few things to keep in mind when considering the partition setup and the order of setup operations needed for booting all of these operating systems:

Windows 98

Windows NT 4

Windows 2000

The common thread here is that all three operating systems understand FAT16. All of the operating systems need a partition to store the key files needed to initiate the system boot process. Some of the key files are:

The cleanest way to achieve this will be to make our C: drive a small FAT16 partition. I also like using this partition to store basic drivers like Ethernet to make the setup process easier. So the final partition table:

Drive FS Size Purpose
C: FAT16 512 MB Boot/Util
D: FAT32 12 GB Windows 98
E: NTFS 4 GB Windows NT
F: NTFS 12 GB Windows 2000

Windows 2000 actually assigned itself drive H:, after the CD-RW and DVD drives. Don’t know why, but didn’t want to fight it…

FreeDOS

After the Linux fdisk fails, I tried with the Windows 98 fdisk. I’m using a 73 GB hard drive and fdisk included with Windows 98 doesn’t properly support a drive this large. Every time I started fdisk it reported a different drive size. Also, every time you made any change it would run “checks” on the disk that took absolutely forever.

I tried a different and ultimately more successful route: FreeDOS. I tried the normal version and it failed to boot. Turns out I needed the “Legacy” version.

Here’s what you do in FreeDOS:

Now we’re ready to create a couple more partitions:

Sidenote: At this point I actually booted off a Linux Live CD and used rsync to copy Ethernet drivers off of my NAS to the C: drive for Windows 98 and NT.

Windows 98 setup

Boot from your Windows 98 CD now. We’ll use its native format for the D: drive. Remember, C: is just for booting.

I like to copy all the installation files to the disk so I’ll never be asked for the CD again.

Important: Windows 98 setup defaults to C:\WINDOWS as the installation directory. This isn’t what we want! Change this to D:\WINDOWS. The rest of setup goes on as usual.

Windows NT 4 Setup

Once Windows 98 is done setting-up you’re ready for Windows NT. Boot off the CD and start the installer.

Even though NTFS supports large partitions, the partition on which you install Windows NT is limited to 4 GB. There’s no way around this. So create a 4 GB NTFS partition.

The rest of installation will continue as usual. When the system reboots you’ll get a boot loader screen that includes “Microsoft Windows” and “Windows NT Workstation 4.00”. The former is the detected Windows 98 installation. You can change the labels later by editing C:\boot.ini.

After installation is complete, you must install at least Service Pack 4 before installing Windows 2000. If you don’t, your NT installation will be unbootable after installing Windows 2000. Windows 2000 uses NTFS 3.0 which Windows NT doesn’t understand until Service Pack 4. Since Windows 2000 replaces the NT-related boot files on C:, an incompatibility arises.

A note about Zip drives

I installed an ATAPI Zip drive in the system since they’re great. However, I found that after service-packing NT, the Zip drive and OS drive letters got swapped. I repeated this twice. This renders the system totally broken since the system drive letter is stored in many places in the registry and configuration files. It’s pretty much unfixable. So to avoid this problem I just kept the Zip drive unplugged until NT was up to date on service packs.

Windows 2000 Setup

You already updated NT4 with service packs, right? Right?! If not, read above before you brick your NT 4 install!

This is the easiest of the lot. You have your choice of file systems (but of course you’ll use NTFS, right?), no partition size limit, and minimal fuss in general. When you’re done you should see a boot screen similar to the one at the top of this page!

Posted 28 Aug 2018