Windows Server 2008, like Windows Vista and Windows XP SP3, has free-look evaluation period, which more commonly known as “activation grace” period. However, Microsoft is more generous on Windows Server 2008 than Windows Vista, where it allows activation-free evaluation period of 30 days after installation. And, as with Windows Vista, user can ‘rearm’ to extend or reset the activation grace period for another fresh 60 days trial usage for up to 3 times.

So Windows Server 2008 system can run for up to 240 days without requires to activate online or offline via phone. 240 days is almost equal to 8 months of free usage without restriction and limitation, and any edition of Windows Server 2008 may be installed without activation for the maximum evaluation period of 240 days. Note that if you’re using Windows Server 2008 Evaluation DVD package, after installation it’s immediately a 120-day initial evaluation period, which the activation grace period can only be extended or rearmed once in this case.

To enjoy the free activation period in Windows Server 2008, users need to install Windows Server 2008 without activating it. To do so, run the Windows Server 2008 Setup program, but do no enter any product key when prompted to enter a product key for activation. Then, click “No” when asked to confirm your selection. The initial 60-day evaluation period which do not require activation be done starts after installation finished.

How to manually extend the activation grade period on expiring

When the 60-day activation grace period is about to expire and end, run the slmgr.vbs script to reset and extend the evaluation period for another new 60-day trial evaluation period, with everything including programs installed and data intact.

  1. Open an elevated privilege command prompt.
  2. Type the slmgr.vbs -rearm, and then press Enter to reset the activation grace period to 60 days.
  3. Restart the computer.

To check the status or time that is left on current activation grace period or evaluation period, run slmgr.vbs -dli command to display the number of days that are left in the current 60-day evaluation period.

User can also use Task Scheduler to automatically rearm activation grace period on expiry.