Installing Ubuntu Server through SSH

Does anyone know if it is possible to install Ubuntu server headless?

I do know of the ability to output a terminal to a COM port, BUT, I was wondering if there was a way to drop a prompt, install SSH, and relaunch the setup through SSH.

I used this tutorial https://help.ubuntu.com/community/Installation/NetworkConsole to setup a network console.

Yes, it is possible.

One way to do it would be to setup a debian/ubuntu livecd that boots up with an SSH server running. Then you can ssh in manually partition and create file systems, and then run debootstrap. This method of installation is pretty advanced, you will have to have a pretty good understanding of how to build filesystems, how to setup boot loaders and so on.

You could even skip the livecd step and netboot a linux environment that starts up an SSH server.

Another method might be to completely automate the installation by remastering alternate installer cd with a preseed file.