As organizations plan a migration from Microsoft Windows NT to Windows 2000, they must decide what to upgrade first: the servers or the workstations. The consensus seems to be that it’s better to upgrade servers first, for a number of technical reasons, but some admins—such as TechRepublic member Iazzdevil—would rather start with the workstations. Lazzdevil posted a question in our Technical Q&A asking what issues might arise from a workstation-first approach:

“I have seen that many people recommend upgrading the servers to Win2K before upgrading the workstations. What are the ramifications of doing the reverse—upgrading the workstations before the servers?”

Several TechRepublic members responded with the general recommendation that the servers be upgraded first, and they offered some suggestions on how to approach the process. The information they offered could be helpful for anyone preparing for a WinNT to Win2K migration.

Issues and recommendations
Tim Walsh, a network admin with Sparta, Inc., pointed out that upgrading workstations before servers would prevent the use of Win2K Server’s Remote Installation Services (RIS). RIS can make the upgrade easier by letting you set up the clients remotely without having to physically access each one. If you upgrade your workstations first, you may subject yourself to a lot of unnecessary manual work.

But he added that this might be a moot point if you’re not performing a clean install.

“If you plan on upgrading workstation OSes versus doing a clean install, RIS cannot be used (neither can Sysprep). If this is the case, it really comes down to a matter of preference.”

Greybeard770 outlined some other advantages of starting with the servers.

“Upgrade the servers first so they will be ready for the workstations. In fact, it’s best if you can add a new server to be your first W2K domain controller. That way, if there is a problem, you can get back to where you started much easier.”

Greybeard770 also pointed out that upgrading the servers first enables you to set up Active Directory (AD) for the workstations.

“After you get a Win2K server running, you will have the AD structure with dynamic DNS, WINS, DHCP, sites, group policies, and organization units in place to support the workstations rather than going back and doing that later.”

Greybeard770’s approach essentially establishes the foundation of the network before upgrading the individual hosts that use it. This lets you take care of more complicated issues before tackling the repetitive tasks involved in upgrading the clients. And, as Walsh pointed out, WinNT workstations can still function in a Win2K domain.

Member wwwacny said that upgrading the servers first gives you a chance to become familiar with the Win2K server environment before upgrading the workstations.

“The servers are the most important, so you want to put a lot of effort into getting their services up in Win2K before you start the tedious task of upgrading the workstations.”

Wwwacny offered an example from personal experience to illustrate the need for addressing server issues first. Once, he upgraded the primary domain controller (PDC) to Win2K after upgrading workstations on the network to Win2K Pro. Later that day, he was forced to roll the PDC back to WinNT 4.0. Because the Win2K Pro machines thought they were on a Win2K domain, he had to remove them and add them back so that they could authenticate.

Other than issues such as this, however, wwwacny said that it doesn’t matter whether you upgrade the servers or the workstations first. In fact, he’s consulted for companies that have taken both approaches to migrating from WinNT to Win2K.

“What does matter,” said wwwacny, “is that the first domain controller you upgrade is the PDC.”

Wwwacny added that you should verify that your third-party applications are compatible or that upgrades to support Win2K are available for the applications you use. He also advised against upgrading from Win98 because of settings and files that you might not want to carry over.

“For those machines, you can use Win2K RIS to push [clean] installations.”

Although one member pointed out that upgrading the workstations first is a viable option, everyone who responded to lazzdevil’s question offered good reasons for starting with the servers. Upgrading the servers first allows you to take advantage of RIS if you’re doing a clean install on the workstations, configure ADS and prepare it for the clients, and avoid reconfiguration of the workstations after upgrading the servers.