Extend The Windows Server 2008 Evaluation Period
Windows Server 2008 may be installed and evaluated for a period of 60 days. This evaluation period can be extended or re-armed a further three times giving a total evaluation period of 240 days!
To begin with install Windows 2008 without activating it by running the setup and when prompted for an activation key do not enter anything and then click No to the message that appears. The 60 day trial period begins when the setup process has finished. Microsoft provide a script that can tell you how long you have left before your activation period expires to run the script open a command prompt and type the following slmgr.vbs –dli you might have to wait a moment while the script runs.
You will then see a dialog box showing you the time remaining until activation is required.
To extend your activation period for a further 60 days you can use the same script but with the –rearm switch as shown below (only do this when your first 6-0 day activation period is nearly finished though!)
Microsoft has an XML code example on their site available here http://support.microsoft.com/default.aspx/kb/948472 that can be used with task scheduler to make this process happen automatically.
