Generally it is not secure to allow remote root login. Additionally, using Password Authentication is also insecure. So… after setting up my server at RackSpace, the next step was to setup basic SSH login security.
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It seems as if by default a VirtualBox VM (Virtual Machine) will start with a network connection set to NAT. This makes it a little difficult to connect to server services running on the VM (such as SSH, Apache, etc). An easy solution is to use the Host Interface directly as described here.