Windoze only like one partition on primary HDD set active, so will booger up previously active partitions on a second drive sometimes. So you can boot a linux live CD or USB and run the partition manager to set the partition you want active... and hopefully that works, if they previously had all the boot files in place... alternatively boot a windows install disk to command prompt and fight through the windows process of fdisk or parted or whatever it is now, always have to google it, doesn't stick for some reason.

ISTR that the NT boot loader allowed you to add an entry into an ini file thus creating an additional entry in a boot menu displayed early on in the boot process.

Or put another way - your first objective should be to get Win 2000 booting first, then add ability to boot Win98 via the Win2000 bootloader.

Hi,

Having a single an appropriate active partition would be the first thing to check, but the issue here might be the need to install the bootloaders. On win 2000's it should be relatively straightforward....
https://kb.acronis.com/content/1507
And then you could try adding a boot entry for Win 98 in that boot.ini file.

But if you also need to rebuild win 98's bootloader I don't have much useful info about that...

IIRC, while you get win 2000 to boot to be able to boot 98 from there, that is chainloading both bootloaders so both should exist.

Of course I would take a snapshot of both partitions as a first step.
Macrium Reflect Free edition could be a good choice if you don't have a favorite already.

For an alternative path you could try Linux Boot Recovery CD which would install grub on your drive's MBR with a boot entry for every OS it finds. Use the 32 bit edition as the x64 will bark about not 64 bits OSes.

Any error text the boot process shows will serve as a hint of which stage it is failing at and what piece could be missing.

Edit: On a final note, remove any non-essential hard drives to avoid messing them with tools and commands that deal with your partitions.

You can see if some tips here help:
https://cloakedthargoid.wordpress.com/win9xme-2kxp-dualboot/

I suspect in your case that all the boot files were actually on the primary hard drive, so the process may be a bit trickier than what's described above. As you were told, you may need to completely reinstall the bootloaders.

Normally, it's easier if Win9x is installed first, then Win2K. To fix the boot without reinstalling all of Windows, you may need to do a SYS C: from a Win98 installation floppy/CD, then run a repair procedure from the Win2K installation media.

How are the partitions organized on your current drive, and how were they organized on the old (failed drive)?

BitWrangler wrote on 2021-08-12, 01:00:

Windoze only like one partition on primary HDD set active, so will booger up previously active partitions on a second drive sometimes. So you can boot a linux live CD or USB and run the partition manager to set the partition you want active... and hopefully that works, if they previously had all the boot files in place... alternatively boot a windows install disk to command prompt and fight through the windows process of fdisk or parted or whatever it is now, always have to google it, doesn't stick for some reason.

I used FDISK and set the new drive as 'Active', but still no boot.

You can see if some tips here help: https://cloakedthargoid.wordpress.com/win9xme-2kxp-dualboot/ […]
Show full quote

You can see if some tips here help:
https://cloakedthargoid.wordpress.com/win9xme-2kxp-dualboot/

I suspect in your case that all the boot files were actually on the primary hard drive, so the process may be a bit trickier than what's described above. As you were told, you may need to completely reinstall the bootloaders.

Normally, it's easier if Win9x is installed first, then Win2K. To fix the boot without reinstalling all of Windows, you may need to do a SYS C: from a Win98 installation floppy/CD, then run a repair procedure from the Win2K installation media.

How are the partitions organized on your current drive, and how were they organized on the old (failed drive)?

I think you are right (the boot files were all on the old primary drive) and the bootloaders are gone.

Now there are two partitions -- C: (the FAT32 partition that has Windows 98 on it) and D: (the NTFS partition that has Win2000), both are the same physical drive.

Hi, […]
Show full quote

Hi,

Having a single an appropriate active partition would be the first thing to check, but the issue here might be the need to install the bootloaders. On win 2000's it should be relatively straightforward....
https://kb.acronis.com/content/1507
And then you could try adding a boot entry for Win 98 in that boot.ini file.

But if you also need to rebuild win 98's bootloader I don't have much useful info about that...

IIRC, while you get win 2000 to boot to be able to boot 98 from there, that is chainloading both bootloaders so both should exist.

Of course I would take a snapshot of both partitions as a first step.
Macrium Reflect Free edition could be a good choice if you don't have a favorite already.

For an alternative path you could try Linux Boot Recovery CD which would install grub on your drive's MBR with a boot entry for every OS it finds. Use the 32 bit edition as the x64 will bark about not 64 bits OSes.

Any error text the boot process shows will serve as a hint of which stage it is failing at and what piece could be missing.

Edit: On a final note, remove any non-essential hard drives to avoid messing them with tools and commands that deal with your partitions.

Thanks for the suggestions, I will take a look.

chublord wrote on 2021-08-12, 16:23:

Now there are two partitions -- C: (the FAT32 partition that has Windows 98 on it) and D: (the NTFS partition that has Win2000), both are the same physical drive.

If you start from a Win98 startup disk / CD, you should be able to see your FAT32 partition as C:. Then running SYS C: should reinstall the bootloader. Make sure the FAT32 partition is marked as active, and you can get Windows 98 to boot from your primary hard drive.

You may need to configure the paths in MSDOS.SYS to get it to correctly launch Windows 98. However, the question is - what drive letter did Windows 98 used to see itself on back when it was working? Because if it remembers that it used to be the D: partition, then it may have many things hardcoded to D:\WINDOWS and D:\PROGRAM FILES etc. Then you can have a problem actually running the GUI.