Windows Server 2008 — strong password and reboots required
HowTo upgrade Windows Server 2003
Lab Notes January 30th, 2008
By Roger Howorth

The first thing we noticed about Windows Server 2008 is that installation is generally much simpler than with previous versions.

As the forthcoming WS2008 is not yet supported by VMware, we created a Windows Server 2003 Enterprise Edition virtual machine (VM) using VMware Workstation 5.5.5. Having done this, we booted the new VM with our WS2008 RC1 DVD and waited a few moments for the installation utility to load. This asked us about our location and language setting, which we changed from the default value of “English (American)” to “English (United Kingdom)”. We were also asked for a license number and if we wanted a GUI or not. Had we run the DVD in an existing Windows Server system we’d also have been given the option to upgrade or do a clean install. With these three simple questions answered, the installer ran from there till the end without stopping.

With our new system installed and booted we ran into the first surprise. We were immediately asked to set a strong password for the administrator, and could not proceed to the Windows GUI without completing this step.

In the new world of Windows Server 2008, a strong password must contain numbers and non-alphanumeric characters as well as ordinary letters. It seems the days of setting the admin password to a family member’s name or even to “password” are long gone.

After installation, there was 1.41GB of free space left on the 8GB C:\ drive, which is about the same amount of space that’s needed for Windows Server 2003 Enterprise Edition.

With our system up and running, we added VMware Tools utility software, which went on without a hitch. However, we needed to reboot the server to complete this installation.

Next we looked at the Initial Configuration Tasks wizard and tried adding some server roles. But the first thing this wizard did was to ask us to check for updates, so we went back and did this. It also asked us to check that we had a strong admin password and static IP address, which of course, we did.

It turned out that two updates were available, so we tried to add them. After adding these we were told we needed to reboot the server before we could continue.

It seems the requirement to reboot the system after adding patches or even seemingly inconsequential software, such as VMware Tools, will be with us for some time to come.