I recently decided to upgrade my Exchange 5.5 servers to Exchange 2000. I thought the process was going to be simply a matter of running a Setup program and answering a few questions. Was I ever wrong. Upgrading to Exchange 2000 is a tedious process, requiring extensive preparation work. In this article, I’ll walk you through a real-life upgrade. I’ll also discuss the necessary preparation work.

Before you begin
Before you perform any of the techniques that I describe in this article, I strongly recommend making a full backup of every Exchange server in your organization. I also recommend trying out Exchange 2000 on a test network that’s isolated from the production network before implementing Exchange 2000 into a production environment.

Microsoft reports that, in many cases, the upgrade process is disastrous. Therefore, I recommend thoroughly testing the process before you implement it on your production network. I also recommend making sure that you’ve got a good backup so that you can revert to Exchange 5.5 should the entire process go belly up. In case the process doesn’t work for you, I’ll share some alternative methods at the end of the article. With that said, let’s get started.

Unfortunately, upgrading an Exchange 5.5 server to Exchange 2000 requires a little bit of advance work. Check the Daily Feature entitled “Preparing to install Exchange 2000 into an Exchange 5.5 environment” for a detailed discussion of some of the things you should do before running Setup.

Installing Exchange Server 2000 (Finally!)
On the splash screen, click on the Exchange Server Setup icon. The server will launch the Microsoft Exchange 2000 Installation Wizard. Click the Next button to get past the wizard’s introduction screen. At this point, you’ll see the end user license agreement. Select the I Agree radio button and click Next to continue. You’ll be prompted to enter your CD key. Enter the key number found on the back of the Exchange Server 2000 CD jewel case and click Next.

After the installation wizard confirms the CD key’s validity (this can take a few minutes), you’ll see the main Setup screen, as shown in Figure A. I’ve seen this process take as long as 10 minutes. The reason for the delay is that the Setup program is analyzing your server to determine which components are already installed, along with their version and location. Therefore, if Setup appears to disappear or stop responding, wait it out instead of rebooting or rerunning Setup.

Figure A
Select which Exchange components you want to install.

As you can see in the figure, this portion of the Setup process is quite a bit different from what you’ve encountered when installing other Microsoft products. You’ll notice that the first line in the Action column contains a dotted line and a down arrow. The down arrow means that an action is required. If you click the down arrow, a menu will appear. Select the Upgrade command from the menu and you’ll probably see an error similar to the one shown in Figure B. This error is only one of a variety of errors you may encounter if you haven’t properly prepared your server.

Figure B
You may encounter this error or a similar one if you haven’t properly prepared your server.

So why did I show you an error like this? Two reasons: First, I wanted to show you that there’s no getting around the preparation work. Second, the process of clicking the down arrow and making a selection is the process you’ll use whenever you add Exchange components.

If you’ve done all of the preparation work correctly, the screen you’ll see will look more like the one shown in Figure C. Notice that all of the upgrade fields are already filled in for you and everything else is grayed out. The reason is that you can’t install additional components during an upgrade. Additional components can only be installed after the upgrade is complete. This screen is simply a summary of the components that will be upgraded.

Figure C
This is what a correct upgrade may look like.

After you’ve looked at the summary screen, click Next. The following screen will prompt you for the password for the Exchange 5.5 service account. Enter the password and click Next.

At this point, you’ll see one more summary screen. As you can see in Figure D, this screen displays the components that will be upgraded without all of the clutter. It also displays the disk space requirements. Once you’ve looked at this screen, click Next to begin the upgrade process. The setup process will begin copying files and upgrading your databases. This process can take a very long time. When the process completes, click the Finish button. Exchange 2000 is now installed.

Figure D
The Setup program displays a summary screen of the components that will be installed.

After the upgrade process completes, you may be tempted to use the Exchange Administrator to go in and look at Exchange 2000. However, although the installation process leaves the Exchange Administrator installed, it doesn’t work in Exchange 2000. Instead, you’ll have to use a variety of Windows 2000 components to look at Exchange 2000. For example, you can use the Active Directory Users And Computers console to set up or reconfigure mailboxes. Likewise, you can use the Services console to check up on the actual Exchange services. Finally, you can use a new tool called the Exchange System Manager to take care of most of the other Exchange-related tasks. You can see a sample of the Exchange System Manager in Figure E.

Figure E
The Exchange System Manager can be used for many Exchange-related configuration tasks.

What if the upgrade didn’t work?
As I mentioned earlier, Microsoft has suggested that sometimes the upgrade process may be disastrous. If this is the case for you, you still have other options. I suggest that, rather than upgrading an existing server, you use either the move mailboxes method or the leapfrog method. Here’s how the process works.

You start by bringing an Exchange 2000 server online as a part of the existing Exchange 5.5 site. Of course, this means that you’ll need some extra hardware to get the job done. Once you’ve brought the new server online, you can use the Active Directory Users And Computers tool to move the mailboxes from the Exchange 5.5 server to the Exchange 2000 server. From here, you have a choice to make. You can either use the Exchange 2000 server as a replacement for the Exchange 5.5 server or you can use it as a temporary server for a leapfrog upgrade.

A leapfrog upgrade involves reformatting the server that you wanted to upgrade in the first place and installing Exchange 2000 on it. You can then move the mailboxes from the temporary server back to the original server. The advantage that the leapfrog method has over the move mailbox method is that if you simply move the mailboxes to a new server and leave them there, you’ll have to reconfigure all of the clients to look for their mailboxes in the new location. This can be a very time-consuming process. However, if you use the leapfrog method, all of the clients are already pointing to the correct server.

Whichever method you use, you should know that the process is very time-consuming. Large servers could take days or even weeks to migrate. You should also know that the migration process generates a considerable amount of network traffic. Therefore, you should plan your upgrade method very carefully.

In this Daily Feature, I’ve walked you through the process of upgrading from Exchange 5.5 to Exchange 2000. I’ve also provided you with screen shots and notes from my own upgrade process.
The authors and editors have taken care in preparation of the content contained herein but make no expressed or implied warranty of any kind and assume no responsibility for errors or omissions. No liability is assumed for any damages. Always have a verified backup before making any changes.