Shoutbox

Your Windows Messenger version is outdated, download the latest version here.

By the way, Windows Messenger is a corporate, more business oriented version of MSN Messenger. Perhaps you should get MSN Messenger instead. It includes more features and its integration with Hotmail is better. More information on differences between Windows and MSN Messenger here.

If you want Messenger to log in automatically, go to Tools > Options > General tab, and make sure "Allow automatic sign in when connected to the Internet" is checked.