Going from 2.4 to 2.6 kernel has always been pretty problematic because of other changes that are necessary in the system.
The system changes out initrd-tools for initramfs
http://wiki.debian.org/InitrdReplacementOptions
And I remember having to install yaird when attempting to switch..
Also in later 2.6 Kernels (I think it was >= 2.6.12 ) udev replaces devfs.. yet another issue that could leave you with a non-bootable system..
http://www.debian-administration.org/articles/291
how-to get from 2.6.8 to 2.6.14 + kernel..
http://www.dominik-epple.de/Sarge-Li...ird/index.html
Beyond those two items there are several other packages that need to be at certain minimum versions, and several new packages you will need to have installed before trying to migrate..
Needless to say I don't think I ever switched from 2.4 to 2.6 successfully on Debian 3.1 I usually opted for a re-install using the linux26 at boot time of the Debian Sarge CD..
I don't think that is an upgrade I would attempt remotely, since a simple slip up will cause your server to be non-bootable with the new kernel..
Other resources you may find useful:
http://kernel-handbook.alioth.debian...initramfs.html
So basically I'd again like to discourage you from attempting this upgrade remotely.. Maybe install Debian on a local machine with the 2.4 kernel, then work out HOW you can accomplish the upgrade successfully over an SSH connection. before even attempting it remotely.
Go to your remote server and export the package list, import the list into your test system and make the package set match..
you know the old :
dpkg --get-selections > selections.txt
dpkg --set-selections < selections.txt
Is there some reason your Production server needs to be on 2.6 ? if not best bet is to leave it alone and just keep applying the 2.4 kernel security updates..