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If you are running a Trial version of Windows server 2008,you can extend the 60 days evaluation period by 3 times.

Follow the steps below to extend the 60-day evaluation period up to 180 days:

1. Click Start -> Command Prompt.

2. In command prompt type

slmgr.vbs -dli 

and press ENTER if you need to check the current status of your evaluation period.

3. To reset the evaluation period, type

slmgr.vbs –rearm 

and press ENTER.

4. Restart the computer.

This resets the evaluation period to 60 days.

For more info browse to: http://support.microsoft.com/kb/948472