What to do if you’re still on Windows Server 2003

Microsoft’s official retirement of Windows XP last year was mainstream news. The end of support for Windows Server 2003 in July has been much quieter, but it’s just as important to think how this might affect your organisation. Like XP, Server 2003 was a successful and well-liked operating system, and many businesses are still using it, having seen little reason to upgrade to later versions. There are probably many setups where this OS is still running on the original hardware, now 12 years old or more! In scenarios such as that, even if the OS weren’t coming to the end of its life, it would make sense to consider upgrading just to refresh the hardware before it starts to fail.

What to do if you're still on Windows Server 2003

If your business is reliant on Windows Server 2003, you may be tempted to stick with it. After all, just because the manufacturer decides that the operating system has reached the end of its supported life, this doesn’t mean it will suddenly stop working. But running a production server without security patches is asking for trouble, and now that the OS itself is officially unsupported, you may hit problems when trying to update the applications and services running on it.

Windows Server 2003 - Lego Servers and obsolete servers

Who’s still using Server 2003?

Businesses are gradually moving away from Server 2003 – but the old OS is far from extinct. According to a recent survey by Vanson Bourne on behalf of the Cloud Industry Forum, Server 2003 usage among organisations of fewer than 20 employees has fallen from last year’s 58%, but remains at a worrying 44%.

The picture is worse for larger organisations with up to 200 employees. Here, 51% are still invested in the obsolete server platform. And when it comes to big enterprise, things look grim indeed: thanks to the complexity of large-scale infrastructure upgrades, 72% of organisations with more than 200 staff are still reliant to some extent on the discontinued operating system.

With so many unpatched systems out there – in many cases running high-profile business services – it’s almost certain that hackers already have Server 2003 in their sights. The sooner you can move to a more secure operating system, the better.

The best upgrade method

So what’s the best way to upgrade the operating system? Don’t even consider attempting an in-place upgrade over the top of the existing Server 2003. For a start, you can’t migrate directly to the latest release: you’d need to upgrade from 2003 to 2008 before moving up to 2012 R2. Even if this process went smoothly, which is far from guaranteed, the amount of downtime involved would cause a lot of disruption to your organisation.

Don’t even consider attempting an in-place upgrade over the top of the existing Server 2003. For a start, you can’t migrate directly

And what will you do if, after the upgrade, you find that some legacy system won’t work with the newer OS? Windows Server has evolved and changed over the years, and several older technologies have been dropped. For example, the multitude of ways in which a program can communicate to a data source has been rationalised: if you have a program that talks to your database via a technology such as RDO, then after the upgrade you’ll find that nothing will work and you need to rewrite the program to work with ADO.NET (although, to be fair, it’s probably time you did this anyway).

Another area that might give you problems is the XML parser, which has changed significantly. Other problems can stem from the level of security set by default in the OS, and while you can disable many of the newer security features and open things up, you need to ask yourself if you really should: if you were starting afresh, wouldn’t there be a better and more secure way of configuring your new server?

Because of problems like these, I’d suggest starting with a clean install of 2012 R2 on a new machine and working from there. At the very least, if your hardware is as old as the OS, upgrade it – although of course by now it may have been virtualised onto a newer box.

Windows Server 2003 - upgrading Image Leonardo Rizzi – Flickr

Your second decision is which version of Server 2012 to use. There are nine in all, the main four being Datacenter, Standard, Essentials and Foundation. There are also two versions of Storage Server, two versions of MultiPoint Server and a Hyper-V version, but these are unlikely to be used to upgrade an existing box as they are specialised for virtualisation, storage, or multiple- user access. If you’re currently using Server 2003 for any of these tasks it might be worth sitting down and rethinking your network structure.

So, going back to the more standard versions of Server 2012 R2, which should you choose? Datacenter is designed for large servers on which you intend to virtualise more than a couple of machines. Not surprisingly, the price reflects this. Standard will allow the virtualisation of a couple of machines and you may well find it’s the best version for your needs, partially because it’s very flexible in its configuration: unlike Essentials, Standard doesn’t have to install as an Active Directory (AD) server. As a consequence of Essentials being an AD server, the installation of a SQL Server database on the same machine is also discouraged, for reasons of security and performance.

if you decide to join a 2012 server to your existing domain, then the whole domain will have to be migrated to the new format

Be aware that if you decide to join a 2012 server to your existing domain, then the whole domain will have to be migrated to the new format, as the schema of the 2012 AD is different. This process is relatively painless, but you must give some thought to any issues that may arise when you upgrade all the domain controllers on your network, and allow time for all the synchronisation to take place between the various domain servers.

Foundation is the most limited version, and normally only available when bought with new hardware. It’s suited to businesses with fewer than 15 users; think of it like the old Small Business Server.

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