Many corporations have fully deployed Windows 2000 across their enterprise, both at the client and server levels. Even if your company sees itself as conservative from a technology perspective, it is likely that you have considered a migration to Windows 2000 in the past several months.

If the clients in your shop are mostly Windows 95, then a motivating factor to migrate may be that the support for Windows 95 will be ending. A move to Windows 98 or Millennium Edition (Me) would be the minimum configuration change required to maintain support. If you are running NT, the only real choice is to move towards Windows 2000 Professional or Server platforms.

Big picture planning
If you plan to deploy Windows 2000 by the end of 2001, what part of the installation will you tackle first? Here are two options:

  • Servers first: If you have a new venture or a minimal infrastructure, then building or upgrading the servers first would give you the advantage of using some of the more advanced migration tools to load the clients in the most automated way.
  • Workstations first: If your environment is already fully developed with many servers and clients, and possibly multiple domains, then upgrading the client workstations first may be the way to go. This method would give the client systems the benefits of Windows 2000 without having to deal with the complexity of moving to Active Directory Services and the associated changes in the domain model.

Most corporations with a fairly well developed server infrastructure will probably opt for the latter approach and get the benefits out to the users as soon as possible, while simultaneously planning the meticulous details of server administration such as name services, routing, domain architecture, etc.

The benefits for the clients are numerous:

  • Improved reliability and robustness
  • The same easy-to-use interface as Windows 9x
  • Full plug and play capability
  • USB support
  • Device manager
  • More control over the desktop and taskbar options

In addition to the immediate functional advances, the client base will be better enabled to take advantage of new technologies such as XML, SOAP, and the newer Web services-oriented applications. New security technology trends, such as Kerberos and Ipsec, are dependent on this version of Windows as a platform base.

The major initial advantage is the stability of the OS over the previous versions. Windows 2000 Professional has proven itself to be more reliable out of the box. Win2K Pro also has several protective features that prevent removal or corruption of critical system files and allow the system to heal or update itself when necessary.

Prepare for the installation
Just like any migration to a new OS, planning and testing are two key components when migrating to Windows 2000.

Planning should answer most of the logical process decisions that you need to make. Testing will ensure that the deployment will go as planned with the targeted client base.

You should take an initial hardware inventory of the target workstations and apply that inventory towards the base minimum configuration that is stated in the Hardware Compatibility List (HCL). Generally any of the newer technology systems available in the past several years are acceptable, but they may need a memory upgrade to get to the base level required for Windows 2000 Professional. Having a utility such as System Management Server can greatly facilitate the collection of this data.

Special consideration may need to be given to the hardware that does not meet the minimum standard. You’ll need to decide whether to upgrade or retire the system. If there is any doubt about the success of the migration, it is better to lean towards the retirement of the older system.

Another tool that can assist in the ascertainment of the compatibility of the target system is using the /checkupgradeonly switch on the Winnt32.exe installation program, or the stand-alone equivalent: Checkupgrade_1.exe. Both will provide you with a list of potential problems with the migration.

A pilot test system
In addition to the cursory HCL and compatibility tests, the applications must be checked for functionality and checked to see if the new operating system causes any inconsistencies. Select one representative system from each major type of target user type. Upgrade this pilot system and test it for verification of the application suite. With adequate planning time, pilot test systems can be installed and given to key users from each target user type. The goal is to fully test the system before mass deployment to that user group.

This is also a very good way to find problems that the workstation support team didn’t catch during cursory functional testing. Windows 2000 has extensive group policy facilities that allow customization of security rights. It also has customization privileges that also can lower TCO by preventing users from making system changes that can corrupt the system. Pilot users should test these restrictive measures to ensure that they do not inhibit work processes.

Select how you will migrate
Finally, consider the various ways that the migration can be performed. One option—the migration can be done on a new system by creating a system image from a pilot machine and then cloning the image for mass deployment. This may be a preferred option for new systems or for systems in which a new disk is being installed. In the latter case, a backup of pertinent data needs to occur to restore the user to a functional system.

The other options include creating an upgrade scenario that can be either distributed via a network share or distributed via a CD-ROM. Consideration should be given to the proximity of a viable network server for use of a shared point of distribution or whether the saturation of the network from large downloads would have an impact on normal work traffic.

Some helpful tools in the creation of automated installation are Sysprep.exe and Setupmgr.exe. The first utility makes a complete copy of system files on the source system and then allows modifications to that image for customization purposes. Sysprep also forces a complete plug and play test to determine if all the hardware components are compatible. Setup Manager is a wizard-driven tool that gives the administrator the ability to modify the installation process from completely customized to completely unattended.

Two valuable tools for the automation and maintenance of a Windows 2000 migration are Remote Installation Service (RIS) and the Intellimirror utility. Both of them require the presence of a Windows 2000 host server. RIS allows a remote boot of a mini kernel, which then starts the actual installation process. This obviates the need for a boot diskette; however, it will work only with newer types of hardware. The Intellimirror utility is a tool that keeps track of user configuration and data so that the target system can be rebuilt from the network even after it has been wiped clean.
Have you completed a migration to Win2K Pro? What advice would you add to this list? What was the biggest problem you faced? Post a comment below or send us an e-mail.