Quadboot: DOS 6.2/Win 3.11/Windows 95/Windows 7/Linux Mint 8...

… and how the hell do I make this work? I need to do this for the following reasons:

  1. Prove to a buddy that it can be done (thus scoring case of swill Coor’s Light)
  2. Run my old legacy programs that I just can’t get to work with the Virtual Machine

I know I am going to need to partition my disk probably into four pieces (two for Linux and one for the 16 bit DOS and Windows 95, the other for Windows 7).

Or maybe I am totally wrong. Its Friday though, and I want me some beer. How do I pull this off?

Some sort of boot partition manager/launcher is the only way I see of doing this. You will need separate partitions.

Honestly this is kind of a stupid bet. Even if possible the cost of a case of beer does not begin to approach the amount of wasted time you will invest is this pointless exercise.

For the curious, what’s the difficulty/why the bet?

Not sure, but I’m thinking you may need actual separate HDDs for this. I seem to recall DOS and maybe even Windows 3.11 having “C:” kind of hardwired. Separate partitions would not allow you to rename the partitions around (easily). But I think the BIOSs will allow you to rename separate drives a little more readily.

First, I would see if Win7 supports DOS/WfW in its multi-boot scheme. From what I recall from doing XP dual-boot systems, the old MS boot loader sucks – and if Win7, even with its boot-loader improvements, won’t handle the other (well, multiple others) Microsoft products, then things just became much more difficult, if not impossible.

At some point not too long ago, I used the “copy the first 512 bytes of an Ubuntu partition to the Windows bootloader” technique to have an XP laptop dual-boot. Well, triple-boot, actually – the reason for doing it in the first place was to preserve Lenovo’s hard-wired recovery bootup functionality, which was just an additional, small, bootable partition. This probably won’t be helpful at all, but the fact that it can be done is not a bad thing to know – although the following article is old and not the howto I used, this looks similar enough and is likely a good starting point to do it.

Furthermore, I’d take a look at the grub manual – the chapter on booting looks like it’d be helpful (check the DOS/Windows section near the bottom, particularly the bits about hiding/unhiding partitions).

Besides that stuff, I’d worry about hardware limitations screwing things up – things like DOS not being able to read large disks or the bootloader having to be in the first…what was it…512 sectors? of the primary disk.

Urgh…not something I’d want to pursue. But an accomplishment if you get it working. Good luck with it…

Well so far I have GRUB2 working Windows 7, My Vista recovery option, and Linux Mint working. The problem I am running into (which I think is the way to pull this crap off) is trying to figure out how to get Windows 95 to install on a USB 2.0 drive. See, I figure I can win this bet because Windows 95 will actually exit into DOS completely. So there, all of them on there. Then I could run 3.1 from the win.exe command (I guess.) But my distribution of DOS 6.2 in on floppy, which I don’t have. I downloaded a copy of the images of the floppies, but I can’t get it to burn to CD. The floppy images are .img and I am looking to convert the .img’s to .iso’s for the CD burner. The burning packages I have downloaded seem to think they can do this, then they take a dump somewhere in the process. Does anyone know of a way to get legit DOS 6.2 loaded on a thumb drive? My TouchSmart can boot from USB, but I just need to con DOS into loading on there. I can load 3.1 from there, and then load up 95.

Astro, I am not one to back away from a crazy bet… so thats why! I was planning on drinking the beer with my neighbors anyway.

If I had any need to boot all of these, I’d use dosbox/qemu/virtualbox to boot everything under Debian/Ubuntu.

Why the USB 2.0 drive? Isn’t that the problem right there? Win 95 predates USB2.0, unlikely to support it at all. How will it read the disk (=thumb drive). Same and more for Win3.1, Dos.

This is not really complicated. Haven’t done it in a while, I am sure google is full of instructions. IIRC, the basic startegy is start with Linux, let it’s boot manager handle everything. During Linux installation, make a fresh partition for each OS, of the right type (FAT for Dos, etc.). Install Linux. Then, install each of the othrs one at a time.

Some Windows, IIRC might overwrite a boot sector, again, google is your friend on how to handle that.

All this should be no problem if you can find the instructions and follow them. The functionality has been in Linux for ages.

What about using Virtual Box as an intermediary? You could install it onto a virtual hard drive from your floppy images, and then take an image of the virtual hard drive, which you then write onto your thumb drive.

The DOS booting to Win 3.1 partition has a 2G limit and the partition needs to be the first part of the drive. No sticking the partition after another partition 40G in size. The partition must also be formatted using FAT not FAT32. Windows 95 also has a 2G size limit and it’s partition needs to be in the first 8G of the drive. It also needs to be formatted using FAT. Dos and Windows 95 will both need a primary partition to work and the boot loader will need to make the correct primary partition boot.

The thumb drive is FAT, so it should read, but I hadn’t thought of the whole 2.0 issue.

I have been googling around but I can’t figure out how to mount the floppy images as drives, and then how would you have it to where you could tell it to go from drive g: to e: to f: to finish the install of DOS on c: or where ever it sits?

I tried using DOSBox to install the Windows 3.1 and 95. DOSBox plays along well with 3.1. but the 95 installer hoses on CHKDSK. :-\

If you mean 95 dies on SCANDISK then use the /is flag when running setup. See 5 of the Best PC Games Right Now - Free PC Tech (bottom has 95 only switches)

Honestly, actually booting anything up to Win 3.11, and probably Win 95, from scratch is just not useful. You can get as much as they’re capable of from virtualization on a modern system. This is probably doable - but in the real world, I can’t imagine a dos app other than fdisk, bios updates, or DBAN that you might need it for. And for those, you’d just boot off a USB stick.

You may find that your DOS programs still won’t run correctly on any machine capable of running Windows 7. Why? Can’t say, but it’s been my experience as far back as the Pentium III days. I think it has something to do with system resources expecting to be allocated by a plug-and-play system that DOS doesn’t have, but I’m just a tinkerer.

Winimage will let you read floppy images. The last version I used (6.1, I think) included a freeware version called “Standard mode”, which would work past the 30 day limit. Copy all the files to the thumbdrive, and make it bootable, and that should be enough to get a bootable DOS thumbdrive.

You could also just copy the floppy image directly to the thumb drive with dd. Instructions are included in that link above. Also, that site has its own copies of DOS 6.22 that come with a utility to copy to a floppy. If it doesn’t check to make sure the destination is a floppy, you might be able to just use that. (If your drive needs to be A: or B:, use subst. It may not be in Win7, but I know it’s there in Win95.)

I’m glad you seem to know what you are doing (you’ve got all the others working, right?). I was thinking when I first saw this that it was something I could do much easier than I could tell someone else how to do, with all the bootloader stuff. (My old hint: Using the grub map and hide commands can be very useful for stubborn old OSes that want to use the first drive only.)

BTW, I hope your computer isn’t like mine which is not compatible with DOS/Win9x. It has something to do with not being able to enable legacy mode on my processor, as my BIOS is locked. Even after installing properly, Win98 would never boot. (I’ve considered using FreeDOS, but that isn’t DOS 6.22, which is what you have to use, right?)

I used to do something very similar back when I was running Windows 95, OS/2, Linux, Netware, and Windows NT, all on the same machine.

You need a boot manager, but you’ll likely need two hard drives. Note that a drive can have up to four partitions, of which one can be an Extended partition. The Extended partition can have other partitions within it.

Don’t worry about getting DOS running from a thumb drive: you can but USB floppy drives, and modern BIOSes will recognise them.

Try this:

Your boot manager may consume a partition.
DOS 6 + Windows 3 needs to go on a Primary partition on the first HDD.
Windows 95 needs to go on a Primary partition on the first HDD. But not the same partition as DOS 6, because Windows 95 runs on DOS 7.
I’m not sure if it’s still a constraint, but for safety’s sake, both the above should be wholly within the first 512 MB of the drive.
Put Linux on the rest of the HDD
Put Windows 7 on the second HDD.

I know I used to have partitions for DOS, Win3.1 and Win95 using the IBM OS/2 BootManager.

I used to resize and manipulate them using PowerQuest’s Partitian Magic and DriveImage - sadly Powerquest was taken over by Symanquest (the dreaded Norton)

I’m not sure about later versions of Windows
DOS certainly needed/needs to boot from what it thinks is a C: drive

If you get this to work with enough time before your friend shows up you should add OSXto the mix. :eek:

I knew I forgot something: if your computer can boot from USB, it does so at the BIOS level, so OS support is irrelevant, as long as you don’t try to hot-swap. And, of course, only the USB drive used for booting will work.

Oh, and remember USB2.0 is fully backwards compatible with USB1.1. You just can’t use HighSpeed mode.

If you have problems getting Grub to boot the way you want it to, you might want to try PLoP Boot manager - I’ve used it on very old hardware that was tricky to set up (and it also adds boot from USB and CD options to older hardware that doesn’t natively support it).

IIRC, installing DOS was just a matter of copying files into the right place and setting up autoexec.bat and config.sys.

Windows 3.11 can be thought of as a DOS application - so that ought to be fairly simple to install once you get DOS in place.

Not sure about the others…