Failed to upgrade from 2.4 to 2.6 several times

[Cojones]

Hello,

I have a Debian machine with an outdated 2.4.27-2-386 kernel and tried several times to update it to 2.6. I tried apt-get, using old .config, using completely new config, some packages and many howtos.
It never worked and I have no idea why. The problem is, that this is a server in some data center and I can only access it via SSH. So whenever a kernel update fails I have no idea why cause I can't see the error.

Might be a stupid question but is there a possibilty to install/compile/update a kernel that definitely gonna work?
I did it successfully a couple of times on other machines but I have no idea what's wrong with this machine...

Any help highly appreciated!

[Cojones]

There's no safe way to upgrade the kernel? Need more info?