Windows 2000's successor has been through three names—Windows 2002, Windows .NET (Win.NET) Server, and the current Windows Server 2003. Amid the confusion of changing nomenclature and last-minute feature additions and subtractions, you might be wondering whether an upgrade to Windows 2003 is worth the effort. Some experts call Windows 2003 merely an "incremental step" forward; others call it "the next generation." How do you know what to believe?

If you're about to begin a Win2K rollout, should you forge ahead or should you regroup and take a look at Windows 2003? In an ideal world, you would be able to determine the suitability of Windows 2003 in your environment with minimal effort. Sure, Windows 2003 is full of great features, such as support for 1 billion Active Directory (AD) objects, tighter security, and many new command-line utilities. But what about the improvements to the OS's main features, such as Microsoft IIS, clustering support, and Terminal Services? Considering how you run your network today, will you actually use these improved features?

Know Your Score

To help you determine whether you should upgrade, I'm going to walk you through my Windows Decision Point quiz. You're going to need a pen, some paper, and a calculator or spreadsheet. To find an answer that's specific to your environment, let's start with three essential questions:

  • What's the size of your business?
  • Which Win2K features are you using today?
  • Which Windows 2003 features can you imagine using in the near future?

After you assemble this basic information about your business, you'll have the foundation for taking this quiz, the goal of which is to determine whether you'll use enough Windows 2003 features to take a much closer look at the new OS.

The impact of Windows 2003 will be different depending on the size of your organization. So, the most important preliminary step is to examine your organization's size by placing it into one of three categories:

  • small—fewer than 100 clients, with 1 to 4 servers
  • midsized—100 to 599 clients, with 5 to 14 servers
  • large—600 or more clients, with 15 or more servers

The Quiz

About 1000 representatives of large and small organizations have taken this quiz. I've presented it at Windows & .NET Magazine Connections and other industry conferences, and many people tell me that it has at least opened the doors for discussion. The quiz assigns point values to each major Windows 2003 feature or scenario. You simply add or subtract points based on your company's size and your use of the technology, then make a judgment based on your final score. Remember, this quiz is simply a guideline to help further discussions inside your organization—don't use it as a rigid gauge for whether you should upgrade.

You'll see that some questions ask whether your organization experiences light, medium, or heavy use of a specific technology. These rules certainly aren't hard and fast; you'll have to use your judgment in each scenario.

Start by giving your organization 10 points.

Question 1: Is Your Business Mostly NT or Mostly Win2K?

This first question might be the quiz's most important question. As you know, Microsoft is retiring Windows NT, and support for the OS is already waning. If you're using mostly NT, you might be aware that you can no longer get boxed NT products, NT-specific Client Access Licenses (CALs), or NT through Microsoft's OEM System Builder channel. Additionally, you'll have to contend with two hard drop-dead dates that Microsoft has set on the horizon (no nonsecurity hotfixes after January 1, 2004, and no paid or online support after January 1, 2005).

If your organization is mostly NT and you have a

  • large business, add 12 points
  • midsized business, add 8 points
  • small business, add 4 points

The scoring for this first scenario is vastly different for large businesses versus small businesses that run NT because small businesses typically require less Microsoft support than larger businesses do. Most small businesses can simply "set it up and forget about it." Although businesses of all sizes will need to contend with Microsoft's forthcoming NT-support deadlines, large organizations will feel more of a support ache if they don't migrate off NT in time.

If you're a mostly Win2K environment, the news is better. Win2K support is officially available for many years to come (at least through 2007). Your Win2K rollout probably resulted in quite a stable platform, and you're likely already happy with the fruits of your labor. However, Windows 2003 brings some compelling new features to the table (as you'll see), and an upgrade from Win2K to Windows 2003 is relatively painless. With these factors in mind, here's my scoring for your scenario:

If your organization is mostly Win2K and you have a

  • small business, add 2 points
  • midsized business, add 3 points
  • large business, add 5 points

Question 2: How Much Do You Leverage IIS?

Windows 2003's new Internet Information Services (IIS) 6.0 is vastly improved over its predecessor. Some of the features IIS 6.0 brings to the table are kernel-mode operation, a built-in IIS Lockdown Wizard, effective bandwidth throttling, and a default-logon change from Interactive to Network. Also, IIS 6.0 is simply much faster and more secure. (For more information about IIS 6.0, see "IIS 6.0 Features," May 2003, http://www.winnetmag.com, InstantDoc ID 38496.) If your organization uses IIS in any capacity, you'll want to take a look at the upgrade. But for the purposes of this quiz, consider how often you use IIS.

If your current use of IIS 5.0 is

  • heavy, add 8 points
  • medium, add 4 points
  • light, add 2 points
  • nonexistent, add 0 points

Additionally, if you currently use IIS 5.0 in front of a firewall in the public address space, give yourself an additional 2 points. IIS 6.0's stronger security features are alone a worthy investment.

Question 3: How Much Do You Leverage Clustering?

Both Windows 2003, Datacenter Edition and Windows 2003, Enterprise Edition support more nodes than their Win2K counterparts do. Windows 2003 Datacenter supports eight-node clusters (increased from four), and Windows 2003 Enterprise supports eight-node clusters (increased from two). Windows 2003, Standard Edition doesn't support clustering but now includes the Network Load Balancing (NLB) feature—a welcome addition. With these improvements in mind, here's how to score:

If your business's current use of clustering/NLB is

  • heavy, add 4 points
  • medium, add 2 points
  • light, add 1 point

You can use Windows 2003 NLB to perform front-end routing for Windows 2003 Terminal Services. This feature is a great way to implement inexpensive load-balanced terminal server farms. If you plan to use NLB this way, add another 2 points.

Question 4: How Much Do You Leverage Exchange?

If you have Win2K, you might also have Microsoft Exchange 2000 Server or Exchange Server 5.5. If you do, your outlook for upgrading to Windows 2003 isn't so rosy. Windows 2003's IIS 6.0 is incompatible with Exchange 2000 and Exchange 5.5. Therefore, if you plan to keep or install new Exchange 2000 or Exchange 5.5 servers within your forthcoming Windows 2003 AD implementation, you'll need to continue to put the Exchange software on Win2K or NT Server.

If you choose to upgrade to Windows 2003 in other areas of your network, you'll simply be supporting two (or perhaps more) server platforms. Ideally, you would want to support just one server platform. However, if you have Exchange 2000 or Exchange 5.5, you'll necessarily have to support more than one. For that reason, if you have Exchange 2000 or Exchange 5.5, you'll have to subtract points for the headache that you'll doubtlessly experience while maintaining multiple server infrastructures.

Windows 2003 offers improved domain controller (DC) and Global Catalog (GC) performance, including the ability to refrain from resyncing all the partial attributes. However, you'll need all Windows 2003 DCs to take advantage of this functionality.

If your business's current use of Exchange 2000 or Exchange 5.5 is

  • heavy, subtract 5 points
  • medium, subtract 4 points
  • light, subtract 2 points

To read about the combinations of Windows and Exchange that Microsoft supports, see the white paper "Microsoft Exchange Server Compatibility with Microsoft Windows Server Operating Systems"(http://www.microsoft.com/exchange/evaluation/ti/tiwin2003.doc).

Question 5: Do You Have Branch Offices?

Windows 2003 introduces many goodies for organizations that have branch offices. The Knowledge Consistency Checker (KCC) can now gracefully handle more (many, many more) than 200 branch-office sites. Also, you can now instruct bridgehead servers not to compress data over WAN links. And you can use the new Install From Media feature to populate DCs from tape or other media, rather than over the network. This feature is quite beneficial in large domains spread across WAN links. Note that all the features (except Install From Media) listed in this category require that every DC in every domain run Windows 2003.

You'll gain the most benefit from these features if you have many branch offices. If you have no branch offices, these features won't do anything for you.

If you have

  • a large number of branch offices (e.g., 50 or more), add 6 points
  • a moderate number of branch offices (e.g., 30 to 49), add 3 points
  • a small number of branch offices (e.g., 1 to 30), add 2 points
  • no branch offices, add 0 points

Question 6: Will You Use Cross-Forest Trusts?

Windows 2003 doesn't bring the nirvana of AD "pruning and grafting" that many systems administrators have hoped for. You can't take another company's Windows 2003 or Win2K domain and "glue" it to your AD forest. However, Windows 2003 does offer one compelling feature for intracompany sharing: cross-forest trusts.

With a cross-forest trust in place, two Windows 2003 forests can more effectively share data and resources between their domains. (For more information about cross-forest trusts, see "Multiple-Forest Trusts," April 2003, http://www.winnetmag.com, InstantDoc ID 38280.) This improvement can be especially helpful should your company acquire another company and want to perform a quick integration. However, all the DCs of both companies must be running Windows 2003 and the domains and forests must be switched into Windows 2003 functional levels.

Windows 2003 also adds the ability to easily rename DCs, as well as the ability to rename domains. However, the procedure for renaming domains is exceedingly painful, and you should resort to it only if absolutely necessary. Still, the capability is nice to have.

If you already have

  • more than two domains and two forests, add 5 points
  • two domains or two forests, add 4 points
  • one domain, add 1 point

If you're planning an acquisition in 3 to 12 months, add another 3 points. Also, if you're planning to rename your company in the same time period, add another 3 points.

Question 7: How Much Do You Leverage Terminal Services?

Both Windows 2003 and Windows XP contain a mechanism for providing inbound connections through Terminal Services. The OSs share a new version of the RDP 5.2 Terminal Services server-side protocol. In general, the RDP 5.2 protocol is more forgiving than earlier versions if you're connecting from a computer over the Internet. Earlier versions of RDP tend to drop the session if even one packet has been lost in transit.

Additionally, Windows 2003 and XP offer a new version of the RDP client-side protocol. The RDP 5.1 protocol adds some whiz-bang features (e.g., 24-bit color, native clipboard redirection, native client printer and driver redirection, bandwidth throttling when connected through LAN versus dial-up connections, time-zone redirection, and Console Session '0') to your Terminal Services experience. You can benefit from these new features only if you use the combination of RDP 5.2 on the server and RDP 5.1 on the client. These features definitely improve the Terminal Services experience so that users feel as if they're using the same system.

If your business's current use of Terminal Services is

  • heavy, add 4 points
  • moderate, add 3 points
  • light, add 2 points
  • nonexistent, add 0 points

Question 8: Do You Plan to Pair Windows 2003 with XP?

XP brings a lot to the table when you pair it with Windows 2003. First, you can perform Universal Group caching, which lets XP clients log on to the network without a GC available. XP also permits secure wireless connections through 802.1x and supports the use of Windows 2003 certificates to validate that connection. Finally, as I stated earlier, XP features the RDP 5.1 client, which—in conjunction with the RDP 5.2 server on a Windows 2003 server (or XP client for use with Remote Desktop)—greatly enhances the Terminal Services experience.

If you'll have

  • XP fully rolled out in 1 year, add 4 points
  • XP rolled out to half your users in 1 year, add 2 points
  • XP rolled out to fewer than half your users in 1 year, subtract 2 points

Question 9: How Much Do You Leverage Group Policy?

I'm a Group Policy junkie. I can't live without Group Policy settings, and I'm betting many of you can't live without them either. With its new Group Policy features, Windows 2003 increases my enthusiasm. First, the OS offers many simple Group Policy improvements, such as the ability to roll back to original default Group Policy objects; about 200 new Group Policy settings for XP, including software-restriction and wireless-networking policies; Group Policy setting support for DNS and Terminal Services; and the ability to perform Resultant Set of Policy (RSoP) calculations.

However, the biggest improvement is Group Policy Management Console (GPMC), a free downloadable tool to help you with Group Policy management. GPMC is a great tool because it adds a Group Policy—centric view to your network. Additionally, the tool permits Group Policy object backup and restore, and offers a gaggle of other great features.

However, to use the GPMC tool, you must commit to licensing at least one Windows 2003 server. Although GPMC is a free download, the product's FAQ clearly states, "You may install an unlimited number of copies of GPMC in your environment, provided you have at least one valid license for Windows Server 2003." Note that as soon as you license and install just one Windows 2003 server, you might be in for a huge uptick in the purchase of Windows 2003 CALs, so be sure that you understand the legal and cost ramifications of your choices. (For more information about the the GPMC tool, see "Windows Server 2003's Group Policy Management Console," July 2003, http://www.winnetmag.com, InstantDoc ID 39190.)

If you

  • use Group Policy heavily, add 5 points
  • are just starting out with Group Policy, add 2 points
  • have no plans for using Group Policy, subtract 4 points

If you're not using Group Policy, you're missing out on many of the benefits that AD has to offer. An understanding of how to use Group Policy will only become more important as Windows networks mature.

Question 10: How Much Do You Leverage SAN/NAS Technology?

Windows 2003 is designed to work with Storage Area Network (SAN) and Network Attached Storage (NAS) devices. With the right hardware, Windows 2003 should be able to boot off your SAN, and you should be able to use standard Windows tools to configure your LUNs. The "open" nature of Windows 2003's SAN and NAS support will likely replace the functionality of today's proprietary SAN and NAS solutions. The kismet between Windows 2003 and your SAN vendor might not be evident today, but be sure to stay tuned: The future is undeniably bright.

If you

  • have SAN/NAS today, add 4 points
  • will install SAN/NAS within 1 year, add 3 points
  • have no plans for SAN/NAS within 1 year, add 0 points

Your current SAN or NAS implementation might not support the Windows 2003 features that I've mentioned. However, you should check with your hardware vendor to ensure that it's working on compatibility with these new features.

Tally Your Score

How did you do? Using the points that you've accumulated, you can now make a fairly informed decision about whether to take a close look at a Windows 2003 upgrade.

You should seriously consider migrating to Windows 2003 if you are

  • a small organization that has tallied 20 points or more
  • a midsized organization that has tallied 30 points or more
  • a large organization that has tallied 40 points or more

If you're still an NT shop, you might want to consider rolling out new servers to Windows 2003. Over time, locating new hardware with NT driver support will become more and more difficult. Additionally, as I mentioned earlier, some serious Microsoft-sanctioned deadlines are fast approaching, and you don't want to be caught off guard.

If you're a mostly Win2K shop, you could feasibly skip Windows 2003. Win2K support will be available for years to come; however, you'll be missing out on some great features. I hope this quiz has opened your eyes to whether you would find these new features beneficial.