With the recent release of Windows Server 2003 (WS2K3), Windows administrators are officially beginning to examine the benefits of upgrading to the new network operating system (NOS). Of course, many administrators are still knee-deep in upgrading to Windows 2000 and Active Directory and are wary of considering Windows Server 2003 yet. Others are quite happy in their state of NT 4.0 bliss and have no plans to upgrade until NT 4.0 drivers are unavailable and Microsoft quits supporting that platform. Whatever your current scenario, this article will present the reasons you would want to consider an upgrade to Windows Server 2003, as well as some of the pitfalls to watch out for when planning your upgrade.

Why upgrade?
To help simplify this issue, let’s break things down into the categories of server features and explore the benefits of each:

  • Web servers: If you currently have a system that is running Internet Information Services (IIS) under Windows 2000 Advanced Server, you should consider upgrading to WS2K3 for the following reasons. First, with the introduction of Windows Server 2003, Microsoft rewrote the way HTTP pages are served. They moved this functionality into the kernel, which fixed numerous problems in previous versions of Windows’ core IIS product. In addition, IIS 6.0 (included as part of WS2K3) has undergone extensive development to make it more reliable, stable, and secure since Microsoft incorporated it as part of the Trustworthy Computing initiative. Second, this release also prepares your network for the introduction of the .NET Framework products. This is Microsoft’s first release in which it incorporates support for the .NET Framework. This framework includes the common runtime library you can use to run code in multiple programming languages. Examples include asp.net and vb.net. Third, if you want to run stand-alone Web servers, Windows Server 2003 Web Edition can save you money on licensing fees because it costs less than the standard Windows Server 2003 version. Finally, my favorite feature of IIS 6.0 is that the default installation of IIS 6.0 is locked down (see this article for information). This is a feature that administrators have wanted for a long time.
  • Domain controllers: There are many new Active Directory features that are part of Windows Server 2003. If you have a large organization that currently runs Windows 2000 Advanced Server, you might want to consider an upgrade. Some new features include a Domain Controller Upgrade Wizard. This new feature allows you to back up your Active Directory database to removable media (including CD or DVD) and restore it to a new machine if necessary. In the past, you had to configure an entire domain controller before shipping it off to a remote location where you wanted to locate a backup domain controller. With the new wizard, you only need to ship the removable media, which will save time and money. Furthermore, Active Directory will now support cross-forest trusts, which is a great feature for companies that merge with other companies and need to incorporate two directory structures.
  • Terminal Services: Terminal Services has made improvements to its Remote Desktop Protocol (RDP) client. One such improvement is the Terminal Server Session Directory. This feature allows you to reconnect to a disconnected session in a load-balanced Terminal Server Farm. Furthermore, the new RDP 5.2 client includes drive redirection, printer redirection, and 24-bit color.
  • File servers: There are vast improvements in the file server realm. WS2K3 offers context indexing, Fat32 on DVD RAM, folder redirection of My Documents, shadow copy restore, and Volume Shadow Copy technology. Volume Shadow Copy is very much like a database that stores changes to files or documents in a shadowed volume. Whenever a user makes changes to a document, they are stored in the database. What does this mean? It means that if the user makes a mistake and then saves the mistake over the original file, you can go to the Previous Version tab in Windows Explorer and restore the file.
  • Clustering: Windows Server 2003 Enterprise Edition and Datacenter Edition now support 8-node failover. If you’re currently running a cluster and need the additional failover support, upgrading would be a good choice. Configuring a cluster in WS2K3 provides a completely new interface, and it’s very intuitive.
  • Group Policy: The upgrade will introduce the new Group Policy management console, which allows better management of your group policies. It will provide a single point of administration for all your group policy needs. With this management console, you’ll have the ability to determine which users and computers have group policies as well as which group policies have been created. In addition, 160 new Group Policy settings have been added to make group policies even more robust.
  • Command line management: With an upgrade to Windows Server 2003, you’ll be able to perform even more administrative tasks via the Windows command line. This will also help you when writing scripts to perform administrative tasks.
  • Server roles: You now have the ability to add server roles to your environment. After you upgrade your server, you can pick a server role from the Manage My Server Wizard, and the wizard will configure your server to be specifically tailored to that role. This gives you the flexibility of not having to keep unwanted services running.

Upgrade requirements
When considering an upgrade, one of the things to examine is whether your current server hardware can handle the new NOS or whether you’ll need to purchase new equipment. The minimum requirements for WS2K3 are not very hefty and do not differ that much from Win2K. Figure A lists the minimum requirements for the four versions of WS2K3; for Enterprise Edition and Datacenter Edition, it also shows the minimum requirements when you’re installing WS2K3 on an Itanium server.
Figure A


Standard Edition


Datacenter Edition

Web Edition
133 MHz 133 MHz (x86)
733 MHz (Itanium)
400 MHz (x86)
733 MHz (Itanium)
133 MHz
550 MHz 733 MHz 733 MHz 550 MHz
Minimum RAM 128 MB 128 MB 512 GB 128 MB
256 MB 256 MB 1 GB 256 MB
4 GB 32 GB (x86)
64 GB (Itanium)
64 GB (x86)
512 GB (Itanium)
2 GB
Multiprocessor support 4 maximum 8 maximum 8 maximum
64 maximum
Disk space 1.5 GB 1.5 GB (x86)
2 GB (Itanium)
1.5 GB (x86)
2 GB (Itanium)
1.5 GB

Security improvements
As you decide on whether to upgrade, it’s important to realize that this release was focused primarily on security. This is the first release in which Microsoft has put the Trustworthy Computing initiative to the test. With security becoming a top concern for administrators these days, upgrading to Windows Server 2003 would be a logical move for the most security-sensitive environments. Some of the security improvements include new features such as 802.1X wireless security, Public Key Infrastructure (PKI), and locked-down IIS installations.

Upgrade preparation
Your first step in preparing to upgrade a server is to introduce Windows Server 2003 into your network or test network. You can do this by either installing a brand new machine or upgrading an older member server that has been retired or isn’t being used for anything. In most organizations, a technical rollout will occur and a test network will be created with a WS2K3 upgrade team. The team would be responsible for all the unit testing that should occur prior to upgrading your production environment.

Once you’re ready to upgrade, you need to have a plan. In the process of planning your upgrade, decide what scenario fits your situation. Are you upgrading from NT 4.0 domains or are you upgrading from Windows 2000 Active Directory domains? When deciding to upgrade, you have to remember to prepare your domain with the Checkupgradeonly tool and the Adprep.exe tool prior to the upgrade process. The Checkupgradeonly option is available via the installation splash screen; the Adprep.exe domain preparation software is available via the I386 directory on the Windows Server 2003 CD.

Test environment
I recommend that you configure a test environment with a NT 4.0 domain controller, Windows 2000 domain controller, Windows 2000 Web server, and two or three workstations (Windows XP and Windows 2000 Professional) for testing connectivity, group policies, and other Windows server features that are critical to your environment. If you don’t have enough systems for this testing, you can download a third-party tool that allows you to run multiple operating systems as different virtual machines. For a tutorial on how to set this up with VMware, take a look at this article.

Once you have these systems configured, you can test the following upgrade scenarios. First, you can upgrade a Web server from Windows 2000 to Windows Server 2003. Next, you can test upgrading a Windows 2000 Advanced Server domain controller (DC) and DNS server. Third, you can move on to testing an upgrade of a Windows NT 4 DC.

Since the product is still in the release candidate stages, you can post messages to the message boards if you get stuck, and play around with all of the new features until you’re comfortable with the upgrade process. Once you feel comfortable upgrading your test network, and you’ve done it multiple times, you can move on to introducing a WS2K3 server into your production network.

Warren’s take
Initially, I don’t see many companies upgrading their DC right away. In my experience, most companies will usually wait until the first service pack to upgrade to a new NOS. Also, several organizations are still planning or are in the midst of implementing Active Directory with Windows 2000 Server. To expect these clients to jump on the Windows 2003 train would not be reasonable.

What I do see happening is many companies taking advantage of introducing Windows 2003 member servers into their network. For example, companies will probably want to update their Web servers to Windows Server 2003 Web Edition to take advantage of the security and reliability enhancements of IIS 6.0, as well as the cost savings in terms of licensing additional Web servers in the future.

Another anticipated development is the 64-bit version of Windows Server 2003 Datacenter Edition. This product supports 128 GB of RAM, a maximum of 32 processors, and 8-node clusters. This is four more than its predecessor. Sitting on top of this 64-bit version will be the 64-bit version of SQL Server that will be able to handle memory-intensive applications and a massive number of transactions. The 64-bit versions of Microsoft’s SQL Server will scale to 512 GB of RAM and support up to 64 CPUs. Its predecessor, SQL Server 2000 Enterprise Edition, only scaled to 64 GB of RAM (with up to 64 CPUs as well). Hold on to your seatbelts when this gets released, because it will finally allow Microsoft to compete with UNIX in the scalable database market.

With the release of WS2K3, you should look for many third-party vendors to discontinue support for Windows NT 4.0. For companies with NT 4 networks, many admins will choose to upgrade from NT 4 to Windows Server 2003 and skip past the Windows 2000 track.