6 Simple Steps To Surviving Windows Server 2003 End-of-life

For many years, the reliable Windows Server 2003 and Windows Server 2003 R2 OSes were the workhorses of IT, used on millions of servers worldwide. However, all good things must come to an end.

With Microsoft ending support for Windows Server 2003 on July 14, 2015, IT departments need to take action now before it is too late. With the deadline fast approaching… what can IT pros do to stave off disaster next summer? TechWeek has teamed up with IT analyst Peter Tsai, of Spiceworks, a professional network for the IT community, to help make as simple and painless as possible.

Step 1 – Identify systems currently running Windows Server 2003

The first obvious step is to see if the OS is on your network. This is a simple task if you have a small server environment, but if you’ve got a bunch of servers to keep track of, it’s best to take stock with a network inventory tool.

Step 2 – Are you actually in a position to migrate and what are the consequences of inaction?

With your existing WS2003 systems, you should evaluate if you really can upgrade. Reasons why some companies might choose not to move away from Windows Server 2003 include: required legacy hardware that doesn’t work with newer OSes, incompatible applications, or if you simply want to live dangerously on a machine running in an environment that will never connect to the Internet (not recommended for security reasons).

If you’re braving the odds for any reason at all, consider the risks and remember that in IT it’s best to err on the side of “better safe than sorry”. You need to lock down those boxes as much as possible if you’re going to keep them around.

Step 3 – Find out which active roles or applications you need to migrate

Once you’ve identified which systems on your network are running Windows Server 2003, you need to check which active roles or applications you need to migrate. Once you understand which WS2003 servers are acting as domain controllers or DHCP, file, email, or database servers (or anything else), you can plan out the next best course of action. There are many step-by-step guides online in Spiceworks and on the Microsoft site that can help you out.

Step 4 – What are the migration options?

When identifying an OS to migrate to, you have lots of choices. If you’re staying with Microsoft, Microsoft Server 2008, 2008 R2, 2012, and 2012 R2 are all good options. There’s a direct upgrade path from Windows Server 2003 R2 to 2008, so you can also upgrade in place on the same machine to get 5 more years of extended support (Windows 2008 Server EOL is in January of 2020).

However, for most of the IT pros we talk to, it makes more sense to jump to the latest and greatest, assuming the apps you’re migrating work with the newest server OSes, and that the server you’re installing the new OS on meets minimum hardware requirements.

As a best practice, it’s good to install a clean copy of a new operating system like Windows Server 2012 R2 (either on a physical box or VM), then migrate the roles, files, permissions, or applications over to the new server so you can test the new box thoroughly before retiring your old hardware.

If you’re purchasing a brand new server (as many might choose to do), you’ll get the benefits of better performance and reducing the risk of failure, since any physical server running Windows 2003 these days is probably getting on in age. Newer Microsoft server OSes also include virtualisation options in the form of Hyper-V, which allows you to better utilise resources, increase server density and save money in the long run.

Step 5 – When should you start your migration?

It’s never too early to start planning. Depending on how many systems you have, the migration process might take many months. Remember that after the Windows Server 2003 EOL date, support and security updates for the OS are gone forever… so it’s never too early to plan.

Don’t get caught out in the open with a vulnerable, unpatchable OS. If you absolutely know that you won’t be able to upgrade on time, take steps to mitigate risk before an eventual upgrade further down the road.

Step 6 – Where to look for help

Microsoft has a full range of guides for many common server roles or services you’ll want to move off of Windows Server 2003, as well as the Windows Server Migration Tool (WSMT), which should help speed things along.

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