HoofedEar wrote on 2023-02-27, 21:46:

I am able to mount the HDD and see all the files. Is it a matter of just formatting my CF card to FAT16 and copying over the files? Or is there some special partitioning that I need to do before that?

To boot DOS you need a valid MBR (doesn't have to be specific), an appropriate executable PBR, and io.sys at the start of the directory; this is not practical with a plain file copy, so it would be easier to copy the disk sector by sector then expand the partition (not sure the latter is practical for MBR+FAT16 on ordinary OS X but the various aftermarket package managers like MacPorts will probably have appropriate tools)

You could also use a VM program that can map a whole real disk and a Win95 "startup" floppy image to install DOS (fdisk /mbr, fdisk to create partition, reboot, sys c:) and then copy all other files...

...but in any case you're almost certainly working in LBA mode, which may be a problem if the PC uses - for that disk size! - a non-linear CHS mapping ("Large" translation as opposed to "LBA") and/or a nondefault geometry...

HoofedEar wrote on 2023-02-27, 21:46:

Any help is appreciated, thanks!

Think different.

Edit: Just kidding. 😜

I'm also half a mac user, so I can see the difference in approaching the situation here.

As Ryccardo said, DOS uses FAT/MBR. You have to take care of different drive geometry systems (CHS, Large, LBA 28,LBA 48 etc).

What Ryccardo says surely is right, but you can also try another approach.

You can make an 1:1 image copy of your old HDD and then write it onto your CF card.

Later on, you can use utilities to change size or add a second partition (recommend).
That way, you can make use of the extra capacity.

a) To make an 1:1 copy, you can use "Win32 Disk Imager" on any 32-Bit Windows.

Just save the device (drive letter) to an image file (say backup.img or backup.dmg).
Then, use that image as a source for your CF card. You can use same program or WinImage or macOS' Disk Utility.

The advantage is, that macOS has image file support since the 1980s.
You can easily mount the backup on macOS like and ordinary drive.

macOS can even read/write 1,44MB floppy disk images, once renamed from *.ima to *.dmg. 🙂👍

b) To make an 1:1 duplicate, you can use Disk Utility.
Simply use the original drive as source for restoration of the CF card.

I don't know the exact steps right now, but I used this method to copy the Mac OS X Leopard install CD to an USB pen drive.

That way, I could install Leopard on a Power Mac G4 without an DVD drive.

Yeah, it's been older Mac systems I did work with, hah. 😅

Edit: Speaking of maximum CF sizes.. Your worries are right.
The classic maximum of both Large (aka E-CHS) addressing and DOS 6.22/Windows 3.1 HDD drivers are 8 GB.

So if you can, please stay within the 8 GB limit. Windows 9x can handle more than this (see LBA-28 limits), but it causes unnecessary confusion between BIOS and Windows.

That's something to keep in mind, by the way.
Windows 95 and the underlying DOS 7 are two separate entities.

DOS asks mama BIOS about the HDD, while Windows uses its own HDD driver.
In some situations, however, the BIOS may be limited or just plainly outdated.

In such a situation DOS/BIOS and Windows will see the very same HDD with different capacity, cylinder numbers, etc.

In short, Windows gets a bit confused. If you then use that extra capacity, data corruption may occur.
Windows will write into areas of the HDD that the DOS part won't see/can't reach during boot.

Then, once ScanDisk runs during boot-up (still in DOS), it will try to correct what it thinks are errors.

That means that the file allocation table gets cleaned from all those entries that ate beyond the borders of what DOS/BIOS can see.

One thing to keep in mind is that the Libretto's BIOS "steals" a bit of HDD space for the end of the disk for itself to do suspend-to-disk with, so that needs to be taken into account when partitioning. I don't recall how it's doing that exactly, but I remember running into enough issues that I ended up installing Windows "properly", setting up everything directly on the actual device.

As for 95 vs 98 - the 50ct is weak enough to already have issues running many 95 era titles so I didn't see a reason to go for 98 on mine.

Wow thank you all for the responses, you guys are quick!

What I ended up doing was following the short guide from this site: https://libretto.rocks/welcome-and-getting-st … -with-libretto/

So from my Mac, I used Parallels and Windows 11 Arm to run Rufus, and install FreeDOS on my 32 GB CF card.
Then I moved the Windows 98SE install files (win98 folder) onto the CF card.
Put the CF card inside and it booted! So I followed the install, everything installed without a hitch.

I then ran into another weird issue. During the Windows install, it had prompted to do something with my PCMICA slot (something about replacing the driver with 32 bit ones? idk I just hit next) but it ended up saying it didn't find anything it needed to replace, and so it carried on. So when I tried to use my PCMCIA CF card reader in my Libretto to read my 2 GB card, it wasn't being detected as a proper drive (it installed the generic IDE drivers, but it wasn't being assigned a drive letter)
So I had to go into Control Panel -> System -> Device Manager and select "View Devices by Connection" and found the drive in "Plug and Play BIOS -> PCMCIA controller" and went into the Properties to give it a drive letter.
I removed the drive, put it back in, and it showed up in My Computer, but it needed me to format it first. And so I did, and now it works! So I'm attempting to install the Libretto 50CT drivers suggested by the above site, I will edit if it works out okay

EDIT: Drivers worked excellently! Except for maybe the audio drivers? When I rebooted after installing the audio drivers, it prompted me for some driver files that I didn't have (like they didn't come with the installer) so I just skipped them and it seems to still work fine!