Very unusual approach. Partitioning, formatting and Win98 install should take place on the target machine directly.

I had a Win98SE tower a long time ago with a ~20GB hard drive but could only get 2.1GB if it to work. 🙁 If you're getting read errors, try partitioning and formatting only 2.1GB and, if it works, using a flash drive to augment the hard drive.

olliethebassett wrote on 2025-09-07, 03:46:

Hello! I am trying to do something that I’m not 100% sure if it would work but I definitely can’t get it to work. I have an 8G […]
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Hello! I am trying to do something that I’m not 100% sure if it would work but I definitely can’t get it to work. I have an 8GB cf card and I want to create an 8GB windows 98 HDD to use with my ide/cf adapter. At some point I got a 4gb to work but can’t get this 8GB to work even though I formatted at fat32.

So I have been using a mixture of WinImage, Virtualbox, images and boot disk to try to get this thing to work.

First I used winimage to create a virtual HD based on the cf card. Then I set the partitions on my modern machine and formatted in fat32.

I then booted the image in virtualbox and installed win98 using a win98 iso. Worked like a dream in virtualbox. Then I used winimage to convert the virtualbox image to an .ima and wrote that to my cf card using windiskimagst. And it won’t boot on my legacy machine (Gateway Essentials 500). Not sure what I’m doing wrong but I have spent many hours with this darn project. Any ideas?

better to install windows in the machine, but first check bios hdd limits

Harry Potter wrote on 2025-09-07, 11:59:

I had a Win98SE tower a long time ago with a ~20GB hard drive but could only get 2.1GB if it to work. 🙁 If you're getting read errors, try partitioning and formatting only 2.1GB and, if it works, using a flash drive to augment the hard drive.

This was your bios limits, first you neesd to check for bios updates, if any, use a overlay before install windows, for example EZ-Drive 9.06 will give you up to 128gb, and is transparent to windows

That system broke, so I no longer need your advice. Sorry! 🙁