Can you still boot to the command prompt by hitting F8 during boot, because in that case it's easiest to just do that. If you can't access your cd drive you could copy the win98 install files to the hard drive and run setup from there.

Otherwise you'll need to make the hd bootable but I don't think that's easy from a modern system.

Using a VM to copy Windows installation files to an HDD image file, making the HDD image file bootable using a bootable floppy image and finally imaging that to the HDD while it's in the USB enclosure could be an option .

The only potential issue I see is if the HDD is old enough to not support LBA, it likely won't work at all in a USB enclosure .

That said, getting a USB floppy drive to make working boot disks on a modern machine is probably simpler .

I would partition and format the drive in the 486, then put it in the enclosure and use a modern PC to copy the contents of the setup CD, drivers, etc to it. You can then put the drive back into the 486, boot a win95 floppy and launch the installer from the hard drive. I do this all the time with my systems. I'll note that I use Linux on my modern computers, so I don't know if there are any quirks to writing to older filesystems from Windows 10. I assume it's fine, especially if the drive is formatted FAT32.

johnnycontrario wrote on 2020-08-13, 18:11:

I would partition and format the drive in the 486, then put it in the enclosure and use a modern PC to copy the contents of the setup CD, drivers, etc to it. You can then put the drive back into the 486, boot a win95 floppy and launch the installer from the hard drive. I do this all the time with my systems. I'll note that I use Linux on my modern computers, so I don't know if there are any quirks to writing to older filesystems from Windows 10. I assume it's fine, especially if the drive is formatted FAT32.

+1 For using using Linux for partitioning and formatting .

+1 Three Linux guys in a row, how often does that happen ?

Akuma wrote on 2020-08-13, 19:25:

+1 Three Linux guys in a row, how often does that happen ?

Happy to be a Linux aficionado, but in this case, it's because there aren't that many functional alternatives .

IMHO, Windows 9x Fdisk has issues with big drives and does not allow the creation of more than one primary partition . The FreeDOS versions exhibit some strange issues as well (Corruption issue when using rloew's TRIM.EXE (TRIM utility for DOS) with FreeDOS FDISK 1.2.1/1.3.1 partitioned DISK ) though, admittedly, these will not be an issue for everyone .

chublord wrote on 2020-08-13, 15:54:

The Windows 98 installation on my 486 got corrupted and it will no longer boot.

I have a USB HDD enclosure. Can I somehow pre-install Windows from a different computer on this HDD using the USB enclosure?

The 486 won't boot from a CD directly, and I don't have any boot disks that work.

I overlooked not having boot disks when I replied the first time around. Doing all the work in a VM and writing the resulting disk image to your HDD is a great way to go, but if you're not familiar with that sort of thing, I had an idea...

Maybe you could use a bootable Win98 CD on a modern computer. I have not done this before, but I know you can still boot to DOS on modern computers and, if I'm not mistaken, newer BIOSes will present USB HDDs to DOS as traditional IDE drives. Connect the 486's HDD via USB to your modern computer and boot the Win98 CD. From a DOS prompt, use fdisk to find the HDD and partition it. Reboot and run format /s to install DOS to the HDD, then boot back into your modern OS to copy the Win98 CD to a folder in the HDD. This hopefully results in an HDD that boots to DOS so that you can run the Win98 installer.

BTW, according to WinWorld, only the OEM versions are bootable:

Edit by Dominus: that page offers illegal downloads

Thanks everyone. I forgot about the "boot from command prompt" option, which worked! I was able to run the Win98 installer from that and make a working boot disk. Windows was still messed up but now I can use the boot disk and format the drives.