Earlier this year, Microsoft released Windows Server Essential 2008, one product in their nascent midmarket arsenal.  For my next few postings here, I’m going to provide you with an overview of the installation process for this new suite of products.

The whole installation of Windows Essential Business Server 2008starts with running the Preparation and Planning Wizard that is included with the product.  Install these tools from the first Windows EBS disc onto a workstation in your organization and then run them.  You can’t skip this step; the server installations require that you provide the results of these wizards to them in order to complete.

Before you begin, insert the first disc of the Windows Essential Business Server 2008 package and install the tools necessary to complete your task.  Specifically, from the root of the first disc, execute TOOLSLAUNCH.EXE.

Windows Essential Business Server Preparation Wizard

The first stage of the installation process consists of running the Server Preparation Wizard.  Once you install the Windows Essential Server Business Preparation wizard, run it by going to Start > All Programs > Windows Essential Business Server > Windows Essential Business Server Preparation Wizard.  Once you start the wizard, you’ll see a screen like the one below.  Click Next to continue.

Install updates

As you probably know, keeping servers current with the latest patches from Microsoft and other software vendors is a critical tool in your security arsenal.  During this phase of the wizard, decide whether or not you want to update the wizard with the latest version available from Microsoft.  It’s highly recommend that you allow updates to install.  Click the Update button to continue.  The download and update process can take a bit of time.

Choose a domain

The Windows Server Essential management and messaging servers also act as domain controllers in your new infrastructure.  The new servers can be joined to an existing forest or you can choose to create a new forest and domain for your new infrastructure.  In this example, I’ll be creating a new forest and domain named example3.com.  In this step of the preparation wizard, decide how you plan to handle the domain aspect of your installation.

Add firewall address

For the next step of the wizard, provide the internal IP address and subnet mask of your internal firewall.  In my lab scenario shown here, the address is

Add subnets

If your overall network consists of multiple networks and subnets, provide a list of them on this page of the wizard.  When you click the Add subnet button, you’re asked for the network’s router address and subnet mask as well as for the type of connection and speed.

You can edit the first discovered subnet by clicking the Edit Subnet button at the bottom of the window.

I have only a single network in my lab, so the only entry necessary is the one shown in the screen below.

Start health scan

The health scan portion of the wizard examines your network to determine its suitability for the new services you plan to add.  The scan looks for issues that could prevent Windows EBS from running properly.  Click the Scan button on this page to begin the scan.

The progress of your scan will show up on the Progress of health scan page in the wizard.  Once the health scan is complete, you’re able to view the scan results on the View health scan results wizard page.  Green check marks indicate success.

Click the Finish button to complete the preparation portion of the wizard.

Windows Essential Business Server Planning Wizard

The next stage of the installation process involves running the Server Planning Wizard, which was installed along with the other tools from the first disc of the Windows Essential Business Server 2008 package.  Go to Start > All Programs > Windows Essential Business Server > Windows Essential Business Server Planning Wizard.  Once you start the wizard, you’ll see a screen like the one below.  Click Next to continue.

Install updates

As is the case with the preparation wizard, the planning wizard provides you with an option to install updates before you continue.  Updates can contain new security patches and other items critical to your new server infrastructure.

Confirm network topology

The wizard’s next step is to make sure that everything is in order with regard to your network.  Earlier in this process, you provided a wizard with information about what networks and subnets are available in your environment.  Now, that information is verified.  In my example, you’ll note that I’m running a single-subnet network, but this may not be the case for your infrastructure.

About your firewall

The wizard asks you a number of relatively self-explanatory questions regarding the configuration of your firewall.  Do you manage it yourself or does someone else do it for you?  How does the firewall’s external interface get an IP address and does the firewall double as a DHCP server for your internal network?

Plan network firewall

Windows Essential Business Server installs  the Forefront Threat Management Gateway on the Security Server to act as a firewall. You can choose to replace your existing firewall with this software, or you can deploy the Security Server behind your existing firewall.  In my example, I’ll install the Security Server behind my existing firewall.

Plan firewall addresses

Now, you get to plan the addressing for your new infrastructure?  The wizard will configure a setup file that creates an additional subnet between your existing firewall and your security server.  Provide the new IP address that you will assign to the inside interface on your firewall.

Record firewall rules

You may have created a number of rules on your firewall that you want to carry over to the new security server.  If you’d like, you can specify those rules here so that you don’t have to worry about them later on.

Plan RWW and SAN

Windows Essential Business Server 2008 includes a feature called Remote Web Workplace (RWW) that allows web-based access to resources in your new environment.  For security, you can configure RWW to use an SSL certificate, but this has to be done separately.  I won’t be going over this step in this article.

Further, you can configure RWW to use a SAN if you like.  Again, I won’t be covering this step in this article.

Plan network settings

Almost done!  Every server in your new infrastructure needs both a name and IP address.  On the Plan network settings page, provide this information for the three servers that will make up your Windows Essential Business Server environment.  Note that the security server already has an IP address.

Save planning data

Finally, save the settings information that you’ve gathered as a part of the wizard.  You’ll need to provide this file to the installation process for each of your servers as you perform their installations.

Here’s a look at the report generated in my example.


This completes the preparation and planning portion of the Windows Essential Business Server installation.  In my next posting, I’ll go over the installation of the management server.