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.
SnapOverflow
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.
You want to use the same way that you can install Debian on NASes and other small systems that don't have graphics hardware -- you just have to have the network-console udeb installed into your installer environment. This then starts up an SSH daemon that you can connect into and do what you want to do. That appears to be what the Ubuntu wiki article you linked to does, although it does remind me why I don't use install CDs any more -- PXE booting all the way.
Also, think very carefully whether you want to stick with manual installs, or just do fully preseeded installations -- by the time you're faffing around rebuilding ISOs, you may as well just go the whole hog and preseed the entire install. That saves you time and hassle all round.