I'm trying to install Debian on a POS machine that I swear is cursed. A Compaq Presario (no, not mine--I would have never bought it...). This nightmare of a machine came with a CD-ROM drive that absolutely *refused* to read every single Linux and BSD CD I ever put in it, prompting me to put the drive in the second bay and put a better CD-ROM drive in as the IDE master, which seemed to do the trick. Pretty much every CD I put in back then after the drive switch booted and worked flawlessly. Now, it turns out the machine refuses to load some CDs--the Debian Squeeze Live DVD, for one--making it impossible to see if Debian supports the wireless card (Atheros AR2413 rev 01 IIRC) which my mom later bought for it, without actually installing it. BTW, I have a feeling the BIOS has a problem with hybrid ISO discs, which the latest Debian Live discs are; back when I replaced the drive and all discs worked, hybrid ISOs weren't common.

[Now that I think of it, it's possible that it's not a DVD-capable drive as I originally thought, maybe that's it... but it doesn't explain why a USB made of it with Unetbootin didn't work either, but one of the official Debian netinst CD worked... other than Unetbootin (in)compatibility with the Debian live image. I need to look further into this...]

Anyway, to the point: I did get the official Debian installation CDs to boot, though. Well, it turned out that the Debian Installer recognized the wireless card, but unfortunately only worked with WEP... oh well, I set the router up for WEP for the installation, hoping that when installed the card would still be recognized and that WPA would be available in the installed system. The computer has the OEM version of Windows XP (BSOD upon upgrade to SP3 was fun ), which thoughtfully (ahem...) decides to install Windows on the entire first hard drive, wiping any partitions that might be there (ie., if you shrunk it and put some Linux partitions or a data partition there, expect the Compaq "restore" system on the "recovery" partition to destroy them... man, the irony in that...).

Anyway, knowing that, I decided to just install Debian on the second drive, which is a measly 20GB compared to the 60GB-or-so drive that Windows is hogging up and claiming its own. The installation mostly went smooth--I got a red error screen a couple times trying to get it to read the network mirrors, but it worked after a couple tries, and everything seemed to go smoothly after that. I installed the basic GNOME desktop and only added the SSH server option. Installation seemed to work. At the end it asked me to put CD 1 back in, so I did and hit enter--and was very quickly taken to yet another (much more serious) red screen, one which no amount of retries would fix: GRUB failed to install. I then tried installing LILO with the option in the resulting overview menu... no luck. I even had the installer verify the integrity of the disc... successfully. If I remember right, it was going to try to install GRUB to the second drive for some reason, with no option to just replace the Windows bootloader on drive 1.

Anyone else have this problem, and is there an easy way to fix? Is there any chance that shrinking the Windows partition on the first drive and doing my original preferred layout (below, second layout) would work?

The drives/partitions as they are now (doesn't work):
Drive 1, Partition 1: Compaq "Recovery" partition, ~5GB
Drive 1, Partition 2: Windows partition, rest of drive
Drive 2, Partition 1: Debian /root partition, ext4, bootable, ~8GB
Drive 2, Partition 2: Linux swap partition, 512MB
Drive 2, Partition 3: Debian /home partition, ext4, rest of drive

The drives/partitions I originally planned:
Drive 1, Partition 1: Compaq "Recovery" partition, ~5GB
Drive 1, Partition 2: Windows drive, shrunk down to 20-25GB
Drive 1, Partition 3: Debian /root partition, ext4, bootable, 10-12GB
Drive 1, Partition 4: Debian /home partition, ext4, rest of drive
Drive 2, Partition 1: Windows partition, all but last 512MB of drive, as extra storage and page file (instead of page file being on system partition)
Drive 2, Partition 2: Linux swap partition, last 512MB, similar as above to keep swap off of system/user drive

Maybe it would help to add that I almost never use extended/logical partitions, only primary ones if I can help it--so all Linux partitions I created on the destination drive (the second one) were primary.

Debian has it's own installer you can partition during installation,when you get to partitioning use guided.
Grub2 is the bootloader, it should recognize your windows installation.
Advanced Options>>Expert Mode gives oportunity to enable non-free repos so that on reboot they're available for installation.

I normally like to create my partitions manually, which I do in the installer with distros that support it like Debian (otherwise I prefer cfdisk). I like the extra flexibility over filesystem sizes and types with the manual Debian partitioner. I have installed Debian several times on my own two machines (Etch, Lenny, Squeeze) in the past with no problem (aside from wireless card and, since Squeeze, nVidia drivers), and I'm running Squeeze right now on my machine. The only difference is... normally I install on the first (or only) drive (and not on such bizarre, crappy hardware). This is the first time I recall having a problem installing Grub in a looooong time, and I've installed hundreds of distros over the years (distro-hopping).

Thanks for the tip about enabling non-free repos from the install, though... I didn't know that.

Either way, the problem was actually not in the partitioning; that part, the formatting and system/main package installation worked fine. It was the Grub installation part that failed immediately.

You can manually partition using debians installer also.

Like I said, that's what I did. That's what I always do.

Either way... f*** this. I give up on Debian. It's 5PM the next day, third or fourth try today, different outcomes every single time. First it didn't finish installing all the packages but Grub installed just fine, then it said a file was corrupt, then it went back to installing everything but failing on Grub. Wow. Seriously, I think it's safe to say I have not had such a pain in the ass with Debian when it comes to install since before Etch.

Well, mods, go ahead and lock this. I'm done. A couple more distros I'm going to try, and then just leave Windows on it as the only OS. BW, I think the drive is CD-only, so there go the choices there--most distros these days (and most of the ones I have downloaded) are in DVD format. Oh well.

Seeing that you have 2 hdd's,when asked did you want to install grub boot loader, are you sure that you selected the appropriate drive?
You have to scroll down to the right 1 & select it.

@UZ64
I just installed debian to a no-name ASUS ME99-VM mobo it can handle 512MB ram, but when installing Ihad to remove ram from 2nd slot to install.

It just failed. I don't remember it asking anything, it just went straight to the error. Every time I selected "install Grub" from the menu, I'm pretty sure it didn't have a chance to do anything but go straight to a red error/failure screen.

Bizarre. I don't know why such a bug would exist, or if it would be hardware or software... hopefully hardware, not a Debian bug. Either way, the machine was just upgraded (maxed out) to 2GB RAM (2x1GB). Not sure if removing a stick would have fixed it.

I just installed Trisquel 4.0.1 (after finding out that the drive does not read DVDs, options are limited, and Trisquel is on a CD-ROM). The live CD booted fine; I recall it recognizing my network and connecting with it in the past with WPA; and the installation (never tried it until now) worked.

I did want Debian on the machine, but oh well. Trisquel will do for now. It's my mom's computer, and she just wants to do custom jigsaw puzzles right now (so I installed Palapeli), and she'll have a fit if the system is unusable any longer. And after all that trouble... I give up on it as I said. Next time I format the drives (or if she decides to ditch Windows completely in the future) then I will probably give it another try.

I think the option is only present when you have 2 drives.
Another thing I did was put another cdrom drive in.