Something like this may be occurring: It may be that the BIOS cannot boot sda2 because Grub gets installed to the boot sector on sda1. A hard drive can only have one bootable partition
and if Grub is in sda1, since that partition is not marked to be booted, it can boot neither Debian nor Windows. Having 2 partitions is like having 2 hard drives. The BIOS looks for Grub or Windows on sda2 and can't find it because it is located in the other, unbootable partition and then you get the error message. So the solution would be to flag sda1 as bootable.
For example, on my system, you can see that /dev/sda1 is marked with as asterisk as the bootable device. If I were to flag another partition, for example, /dev/sda7 as bootable, then I would get the same error because my my Grub bootloader is on the boot sector in /dev/sda1.
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[size=85]# fdisk -l
Device Boot Start End Blocks Id System
/dev/sda1 * 1 1836 14745600 83 Linux
/dev/sda2 1836 60802 473636865 5 Extended
/dev/sda5 1836 2821 7909376 82 Linux swap / Solaris
/dev/sda6 2821 26013 186290039+ 83 Linux
/dev/sda7 26013 27849 14745600 83 Linux
/dev/sda8 27849 28822 7811072 82 Linux swap / Solaris
/dev/sda9 28822 60802 256877568 83 Linux[/size]
Did you install grub to sda1 or sda2?
Grub needs to be in the bootable partition.