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The Procrastinator's Guide to Windows Server 2003 Migration

If you're running Windows Server 2003 on production systems, you need to etch the date July 14, 2015 into your brain, because that's when Microsoft will terminate extended support for the venerable OS. That date is rapidly approaching, so it's time to get moving on your migration plans. The more complex your operation is and the more heavily you rely on Windows Server 2003 to run production systems, the more time and effort you're going to have to put into migration. It's possible that your operation will require three or more months to make the switch, which means that you'd better get on this now.

Migrating from Windows Server 2003 is critically important as extended support for Standard, Enterprise and Data Center (32-bit and 64-bit) will end. This means that there will be no more patches of security vulnerabilities or non-security defects or operational issues. Moreover, third-party products such as business applications will not be supported on Windows Server 2003. No third party could guarantee that their software would continue to run on unsupported systems, because defects might arise in the underlying OS that can't be addressed.

Microsoft has quite a bit of information devoted to figuring out what you need to do. Of course, their suggestions are to migrate to Windows Server 2012 R2, Microsoft Azure, or Office 365. There are a number of alternatives, such as moving to another operating system (Linux) or using cloud-based services. I'll explore these options in a future article. Right now, I'll help you decide how to begin assess the current state of your server software and developing a migration plan.

Getting Started
A good place to start is Microsoft's Windows Server 2003 Migration Planning Assistant, which will guide you through four major steps: Discover, Assess, Target, and Migrate. There's also the Microsoft Assessment and Planning Toolkit for Windows Server 2003 and SQL Server 2005 migration (the latter reaches end of support on April 12, 2016).

Discover is essentially an educational phase to help you learn what to expect and how to do something about it. The fact that you're reading this article means that you're already in the Discover phase. The Windows Server 2003 page includes links to webinars and white papers that explain what you need to do.

One thing that I strongly suggest, depending on the size of your company, is that you put together a short document for the business people (especially the person who will have to approve the budget) explaining why migrating from Windows Server 2003 is important. Explain that the end of security patching could expose business data to attack and that your vulnerable system could be used to attack someone else, thereby creating a liability for your organization. Explain that the risks outweigh any cost savings that might result from simply doing nothing as applications and servers themselves could go down with no clear way to repair them, causing a loss of availability that would affect the business. Finally, relying on an unsupported server operating system for production could place your company in non-compliance with one of business regulation frameworks (such as PCI) to which you must adhere. This last one is a potential gotcha for small businesses who could lose large businesses as customers if they fall into non-compliance. The overall goal of this document is to explain the business impact and to emphasize that the end of life of Windows Server 2003 has serious implications to IT operations.

The next step is to Assess the role that Windows Server 2003 plays in your IT environment. In some ways, you'll be adding detail to the business document that I describe above. In other ways, you're taking an inventory so you can start planning. Begin by simply listing each Windows Server 2003 license in use, the hardware it runs on, the users and groups that rely on it, and the applications that run on it. You'll want to focus on the IT ramifications of all this, which applications might be disrupted, and who will be affected. It might be helpful to take this one step further and assign a business value to each application in order to help prioritize systems for replacement.

As part of your assessment, dig deeper and start making a migration plan by understanding each server's role. The server's role will dictate your migration path. A Windows 2003 Server can be a file server, a Web server, a terminal-services server, or an application server. Know what Microsoft software you're running, whether it's SQL Server, Exchange Server, and/or SharePoint Server. It's also important to know where this server fits into your Active Directory and how you're going to recreate your Active Directory upon migration. Finally, you should catalog third-party and custom applications.

Next you'll want to Target, or plan where you'll migrate your Windows Server 2003 applications. Your options include migrating them to Windows Server 2012 R2 either on new server hardware or virtualized, relocating them to the cloud (for example Azure and/or Office 365), decommissioning them because they are no longer active or can't be supported after migration, or, if feasible, rewriting and moving them to a different platform entirely. Migrating to a new server, either physical or virtual, is probably the most straightforward choice. Relocating to the cloud is likely to require some architectural modifications. Decommissioning or rewriting are probably only options if you have already assessed your applications and made those decisions because otherwise you're going to be severely pressed for time.

Your next step is to Migrate. This is where you'll be replacing Windows Server 2003 with some other option like those mentioned above in the Target phase. Hopefully, you've already done all of the requisite nitty-gritty planning up front. Depending on how complex your existing Windows Server 2003 infrastructure is, this could get pretty hairy. Having been through projects like this before, I cannot emphasize how critical the up-front planning is—you can't simply wing your way through replacing a server infrastructure.

Parting Words of Wisdom
You're not going to want to be responsible for supporting production applications on servers that are beyond end of life, and end of life for Windows Server 2003 is rapidly approaching. In my experience, there is no such thing as an easy and straightforward server migration, so the best thing you can do is start developing a detailed plan as soon as possible. Also, be aware that no matter how much up-front planning you've done, something is going to go wrong somehow so plan for downtime (at night or on the weekend) and consider a contingency plan for complex migrations.

Time is of the essence. Prioritize Windows Server 2003 migration within your organization today.

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