Windows Server 2008 R2 Deployment Considerations

Before you start

Objectives: Familiarize yourself with the things you need to keep in mind when deploying Windows Server 2008 R2.

Prerequisites: no prerequisites.

Key terms: Windows, Server, installation, Core, R2, Datacenter, Enterprise, Standard, activation, edition, upgrade, key

Installation Method

Once we decide which edition of Windows Server 2008 R2 we want to install, we have to determine the method of the installation itself. The thing is, Windows Server R2 can be installed in different ways. We can perform the installation form the DVD, over network using PXE boot, or Windows Deployment Services (WDS). Also, if we don’t have PXE or WDS, we can use WindowsPE (Windows Pre-installation Environment) disk and install the system from the network share.

The installation process is pretty simple. It is image-based. Compared to a file-based installation, which prior versions of Windows Server had, in image-based installations we don’t copy each and every file to the disk. Instead, the whole image is deployed to the computer, which makes installation faster. Also, the number of steps in the installation process is pretty small compared to the installations in previous versions of Windows Server.

Note that during the installation we can install any edition of Windows Server R2 without entering a product key. This enables us to test the operating system in our environment and then activate it when everything seems right. However, we have to be careful to ensure that we choose the right edition during installation (taking into account proper roles and features), since we will need to enter the licence key for the particular edition that we are using once we decide to activate our OS.

Partitioning Disks

How should we partition our disks on the server depends on what kind of roles and features we are going to use. Also, we are going to use BitLocker on the server, we must create a separate partition for BitLocker prior to installation of Windows Server 2008 R2.

Upgrading to Server 2008 R2

We can only perform an upgrade by booting into the current version of Windows and then starting the installation of Server 2008 R2. We can’t upgrade from desktop version of Windows like Windows XP, Windows Vista or Windows 7. Also, keep in mind that we can only upgrade to the equivalent edition of Server operating system, or higher. For example, if we want to upgrade from Windows Server 2003 (SP2, R2), the following scenarios are supported:

  • Datacenter to Datacenter
  • Enterprise to Enterprise or Datacenter
  • Standard to Standard or Enterprise

If we want to upgrade form Windows Server 2008 to Windows Server 2008 R2, the following scenarios are supported:

  • Datacenter to Datacenter
  • Datacenter Core to Datacenter Core
  • Enterprise to Enterprise or Datacenter
  • Enterprise Core to Enterprise Core or Datacenter Core
  • Foundation (SP2 only) to Standard
  • Standard to Standard or Enterprise
  • Standard Core to Standard Core or Enterprise Core
  • Web to Standard or Web
  • Web Core to Standard Core or Web Core

Upgrading between platforms is not supported. This means that we can’t upgrade the 32-bit edition of Windows Server to the 64-bit edition of Windows Server 2008 R2. Also, cross-language upgrades (for example, en-us to de-de) are not supported.

Before upgrading we should always perform full backup of the current installation. This way we will be able to roll back to the previous installation if something goes wrong. We can restore to the previous installation by using the Windows Automated System Recovery (ASR) which comes freely with Windows. Also, keep in mind that upgrading required more free space than regular installation, so we should ensure that we have enough free space on our disks. Implementing BitLocker features in upgrade scenarios can be difficult, so if we plan to use BitLocker we should consider doing the clean installation. Upgrading is great because all the configuration from the previous installation is preserved.

Licencing and Activation

Product activation is the process of validation the authenticity of our software and confirmation that the product key has not been compromised. When it comes to licencing, it is easier to acquire Volume Activation licencing. This way we don’t have to deal with multiple product keys and serial numbers which are related to different purchases, and which are used on different installations. When Microsoft introduced Windows Server 2008, it also introduced two new Volume Activation methods. Those two activation methods are MAK (Multiple Activation Key) and KMS (Key Management Services). When we use MAK, we actually use a pre-defined pool of activations that are located on Microsoft’s own activation servers. Our clients will contact those servers and make sure that they are licenced. This way we don’t have any type of local management structure for our licences. When we use KMS, we actually use local licencing server which contacts the Microsoft server and downloads the available keys and activations. Which method to use depends on the on the size, network infrastructure, connectivity, and security requirements of the organization. MAK is typically used in smaller environments that have a constant connection to the Internet. KMS is typically used in larger environments that have a constant Internet connection and want to manage their own licence keys. Note that activation is not done during the installation, but later. By default, we have 60 days of grace period. After that we have to activate our installation.