Planning the Migration to Windows Server 2008

There are very critical business considerations prior to launching a migration process. As with everything involving software, there are important factors to consider. The costs must be analyzed, compared with the ROI, and see whether the investment is worth it. This article strongly suggests that these steps be taken and completed by a professional in the field. Our focus lies, rather, on the technical side.

First of all, the IT manager needs to know what's new in Windows Server 2008. The foundation is built on the same architecture and core as Windows Vista. This also means that it brings with it the new features, improvements, and security upgrades as Vista. Aside from these, currently there's a SP2 rolled out for  Windows Server 2008. It's great because it fixes most of the incompatibilities and bugs that its ancestor brought.

Here let's mention a few of these new and major features: Server Core, PowerShell scripting, self-healing NTFS, BitLocker drive encryption, expanded AD roles, new protocol to the Terminal Services (RDP 6.0), Hyper-V virtualization, IIS 7.0, NAP, WSRM (Windows System Resource Manager), and a fully functional Server Manager tool that brings a GUI to most server roles -- not to mention lots of security improvements.

Windows Server 2008 comes in the following versions: Standard Edition, Enterprise Edition, Datacenter Edition, Web Server, Storage Server, HPC Server, Small Business Server, Essential Business Server, and Server for Itanium-based systems. Each of these, excluding the latter three, come in both 32-bit (x86) and 64-bit (x64) variations. And the first three should be considered if all we want is to get the most out of Windows Server 2008 and really benefit from its functionalities. 

As a final step before moving on, please check the system requirements for Windows Server 2008 directly from the official sourceby Microsoft. As far as whether that list really applies, you should definitely think about it. They aren't being misleading. Surely, 2GB of RAM might seem to be enough, and that's how it appears on the list, but to put it simply, chances are that you will struggle with the bare minimum. I recommend that 2-4GB be taken to mean 2+.

On the next page we are going to discuss migration considerations. 

Importance of Migration

Scheduling the migration of a server operating system is important. The best approach would be upgrading as soon as possible after the new OS is rolled out, but this usually is not a wise decision at all. Rushing into something new without proper testing of hardware and software compatibilities is a foolish decision. What about bugs? New software just comes with them. But now that Windows Server 2008 comes with SP2, things have changed.

If your business did not require the new features of Windows Server 2008 up to this point, and if you could wait until now, this is great. A lot of IT managers all over the world were not-so-pleasantly surprised; the same goes for system administrators working hard to get everything to work happily together. However, at this time there is plenty of information available; best practices are to be found everywhere, and the entire process is pretty well documented from A to Z, as well as possible problems.

Furthermore, this means that the timing couldn't be better for you to replace your five-plus-year-old server operating system with something new that will increase the overall productivity of your business. Yes, that's certainly true; but more information regarding migration does not necessarily minimize the risks. Risk management should be considered just as important as if nothing is certain.

Every organization runs on a specific customized infrastructure that's unique. Thus, no matter how many guides and manuals are read and followed, each organization's migration steps are going to differ from one step to another. The major steps certainly will not, but still, unique cases can happen everywhere which must be handled carefully. Therefore, please understand that the migration should be deployed carefully. 

The necessary precautions cannot be neglected. Undoubtedly the best and optimal scenario would be where all of the data is backed up and there's a backup server that is able to take over the required server roles -- for example, a backup domain controller. But before doing the migration live, generally it is advocated that the entire process be rolled out in a virtual environment. This is called the staging process of the migration.

Staging the migration may seem to be a waste of time (thus, resources), but that isn't necessarily true. If the system administrators have plenty of experience with the migration of this exact version of Windows Server 2008, then maybe-but only maybe- staging can be skipped because their skill-set is diversified and they have probably already run into numerous issues and can handle everything smoothly. But this isn't advised!

If this is the first time your IT personnel are handling a migration to Windows Server 2008, then it is really critical to research its compatibilities with existing software. Let me just tell you one of the most common situations which should be handled accordingly. Exchange 2007 is not compatible with Windows Server 2008. Neither is Exchange 2007 with SP1. This means that if you migrate, it just won't work!

Now that I have your attention, relax, and read on. There is an official word on Microsoft recommending the following solution. If you want to run Exchange 2007 (with or without SP1) on a Windows Server 2008, then this can only be done if you set up a Windows Server 2008 without having Exchange already; you cannot upgrade. Exchange 2007 must be installed on the top of Server 2008. 

Planning the Migration

First of all, for the consistency of this series we are going to assume that you are already running  Windows Server 2000/2003 as a main server. Therefore, what you want to accomplish is to upgrade your existing server to the new server edition. If you need to expand/upgrade your hardware specifications in order to meet the requirements, please do so. In this case, the IP address and hostname won't change.

There is an alternate way where you are building from scratch an installation of Windows Server 2008, and then transferring your server roles and services one-by-one from your existing server until the new one is able to take over the workload entirely. And perhaps you will still want to run your existing server as a BDC (backup domain controller). Windows Server 2008 calls this feature a read-only domain controller.

In this article series we are going to follow the first route, where we are upgrading from an existing Windows Server 2000/2003 installation that runs all of the FSMO roles along with DHCP, DNS, and other services-DFS, Exchange 2003/2007 and SQL Server. Before we begin, it is recommended that you create a full backup. Clone everything as an image.

In a nutshell, what we want to accomplish is to migrate each of the server roles to Windows Server 2008 from your current server(s)-which is/are running Windows Server 2000/2003. It is possible to split the server roles onto more than one server, and even attempt clustering, but we won't go that far. Here we are going to cover one server running Windows Server 2008 and handling all of the FSMO roles.

Prior to installing Windows Server 2008 we need to analyze its possible versions; they were mentioned at the beginning of this article. Also, we should clarify whether we want to install only the Server Core or not. Moreover, do we want to create a RODC (read-only domain controller), which is what BDCs (backup domain controller) are called now under Windows Server 2008? And finally, what about Hyper-V virtualization?

These are factors that should be discussed intensively at an IT meeting after proper business analysis of the requirements has been done. Don't hesitate to think long-term, because reinstalling a server operating system always eats up resources. Failing to visualize a future-proof scenario might hinder performance, or require a total revamping of the infrastructure or re-installation of Windows Server 2008 in the future.

And finally, once again, remind yourself that in order to turn the migration into a cost-effective process and to fully benefit from every new capability and feature that the new server operating system is able to bring to the table, it is preferable that you also deploy Windows Vista, train your personnel, and so forth. All of these come with a fair amount of costs (licensing costs, hardware requirements, training costs, etc.).

Summing these up, migration to Windows Server 2008 is a process that companies should do while fully cognizant of what is involved. It is not a child's play but neither is it tough. It just implies a lot of factors that shouldn't be underestimated. However, if everything is planned accurately, fairly scheduled, and the migration is executed in time and with great results, then you're going to reap amazing benefits in the long run. 

Taking a Break

As you can see, we have reached the end of this article. In this part of the series we have learned what migration is all about, its necessary major steps, why we should we upgrade, the possible choices of editions, and such.

It's time for us to take a break. However, don't forget to check back frequently because you won't want to miss the upcoming segments of this multi-part article series. In our very next part we'll describe the entire migration process, how to transfer server roles, other must-have services (like DNS and DHCP) and how to configure and utilize those services.

Once our Windows Server 2008 is fully functional and configured according to our needs, then this series will be continued with the new WSUS 3.0, Exchange 2007, and SQL Server 2007. WSUS stands for Windows Server Update Services, and you really shouldn't neglect it. Its configuration isn't that much different, but we thought that it deserves an entire article dedicated to its installation and set up. 

And finally, we can't really finish without inviting you to join our helpful forums at DevHardware Forums. We've a strong base of resident professionals, enthusiasts, and tech experts. If you want to hear opinions on some service or ask some clarifications regarding some details just shoot us your questions. We'll do our best to help. And feel free to pay a visit to the forums of our sister-site: DevShed Forums.