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Whats Your Action Plan?

The Problem

Windows Server 2003 is fast approaching its end-of-life. Microsoft has announced the official date for end-of-life support as July 14th, 2015. While many administrators are well aware of this fact, there are still nearly a million servers across the globe currently running live applications on Windows Server 2003.

It should be cause for alarm that so many businesses are still reliant upon an operating system originally released almost 10 years ago (December, 2005 for Windows 2003 R2). More concerning is that many of these W2k3 servers are running applications originally developed for a 32-bit operating system.

Even if your Windows 2003 server is stable at this time, do you want to risk running your applications on a server that will not ever again be supported starting July 15, 2015?

Consider also that most all hosting service providers will ultimately force their customers to migrate to newer, fully supported platforms so that they can continue to provide the support and security promised in their service level agreements, which will not be possible once the Windows 2003 server OS is officially unsupported.

Unfortunately, WSM has found that the vast majority of businesses neglect to plan their server migration and upgrade with enough lead time, often resulting in a last minute, frantic, stressful and risky forced migration in order to ensure continuity of service, support and security.

This all comes down to the simple matter of maintenance. If youre still running Windows Server 2003, its highly probable that you havent been proactive with maintenance, patching, upgrades, etc.

The problem with a last minute migration approach is when the server/version upgrade results in problems, errors or inconsistencies with security, stability, or functional issues with your applications that require immediate remediation, and most often programmatic revisions.

Needless to say, waiting until the last minute to perform your Windows 2003 server migration is a risky proposition.

Windows Server 2003 End-of-Life Server Options

There exists an understandable (but unwise) reluctance to migrate from a currently stable Windows Server 2003, likely due to fear of the inevitable challenges that administrators and developers may encounter with incompatibilities (especially between 32-bit and 64-bit platforms).

Although some migration tools can aid the migration of some applications/websites, most services still running on Windows 2003 servers are fairly custom and will present unique, specific challenges during migration/version upgrade.

Therefore, best practice to prepare for your migration is to start with a thorough migration and upgrade plan well in advance of the end-of-life date, for the reasons we have stated here.

Your Options

1. Stay Put. In this scenario, you no longer require server support, are prepared for major vulnerabilities, and are perfectly fine to just kick the can down the road.

Assuming you actually rely on your Windows 2003 server applications, this option is only viable if you already are underway with replacing all your applications and servers with a new architecture from the ground up.

In this case, the risk of unsupported servers/applications, security breach, functional errors etc. is outweighed by the benefit of focusing all your resources on the overhaul effort to all-new applications, to replace all the services on your current Windows 2003 server.

2. Upgrade The Server. Performing an upgrade to your existing server, if even an option, in most cases will result in functionality errors with your applications that youll need to resolve in a live environment. Moreover, its likely the server itself is several years old (or more), so youre solving one problem in a potentially reckless, short-sighted manner while leaving the legacy hardware issue for a later date, compounded by having to diagnose and resolve application failures (at an unknown magnitude of time and expense) in your live environment.

This option is extremely high risk, unless you are certain that you wont encounter any significant application errors upon the server upgrade, and your business can withstand a possible services outage of 48 hours (or more), and economy/budget is way more important to your business than longevity, security and support.

3. Migrate and Upgrade. In most all cases this is your best, most logical option. Start with your plan, and start now.

Best practice planning for your Windows 2003 server migration should include phases for project scope (technical and project management), resource allocation, capability (i.e. programmers and testers), and budget. There are more granular components as well, but these are a good place to start.

In summary, the rule of thumb for successful migrations is to plan ahead, be thorough, and dont wait until the last minute if it can be avoided.