There are may reasons why would might like to run a headless Debian server on your home network. I have mine primarily as as file-store, serving video, music and pictures to my Windows MCE PC (you see I'm not one of these Windows hating Linux nerds, use the right tool for the right job I say!). Being headless and tucked away in a dark corner it's important to be able to manage the system with little fuss, and I use ssh to login and administer the system remotely. The question here though is 'When do I know that I need login and do something?'. I ideally want to know asap if there are some important security updates ( apticron ), or that the raid ( mdadm ) has run into some trouble or if some important cron job has spewed some helpful output. Lucky for me is was fairly straightforward to configure the server to email my google mail (gmail) account whenever it has something important to say, and here's how I did it! I have this working on both Lenny and Squeeze.