On Windows Server 2008/2012 it's possible to enable automatic login if the server is NOT a domain controller.
Simply run:
netplwiz.exe
Found under WIN_INSTALL_DIR\System32, and uncheck "Users must enter a username [...]". You'll have to insert you username and password and at the next reboot you'll brought directly to your desktop.
If your server is a Domain Controller (DC) too, then you cannot use this tool, but will have to uncheck the same setting from the "Active Directory Users and Computers" snap-in
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