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Windows Server 2003 End of Support Is Coming – Are you Ready?

Microsoft | Posted on November 20, 2014 by Tim Mckellips

On July 14th 2015, a full twelve plus years after it’s initial release, Microsoft will sunset their support for Windows Server 2003 and all of its offspring like R2, Small Business Server, etc. So, what does the Windows Server 2003 End of Support marker represent? And why does it matter?

Security patches won’t be released. Bugs will go un-debugged. Compliance is no longer met and support agreements get voided, etc. No doubt you have read about all of that. It is important.

Windows Server 2003 was the last 32-bit first Operating System (OS). The last pre-virtualization OS (think market trend not invention). The first ‘trustworthy computing’ OS. While these are all standards now, that wasn’t always the case. While it is interesting to think about where we have been, it’s even more interesting to discuss where we should go. Stop. Hold that thought. We have some work to do before we can imagine the future.

First, why are you running Windows Server 2003?

Softchoice’s recent well-publicized analysis found businesses were unprepared for Windows Server 2003 End of Life.

You need to find out what you have that is running 2003 but, more importantly, address and answer why? What function does Windows Server 2003 provide? It’s answering that question where you have some work to do.

We run servers for a lot of reasons. We install some to run OS integrated services like DHCP, File and Print services, Active Directory, DNS, etc. These are fairly simple to migrate to new servers and typically require strong planning and execution, but are not terribly complex.

Second, what software are you running on Windows Server 2003?

We install others with compatibility flexible software like SQL, Exchange, and SharePoint. Exchange 2007, for example, is able to run on Windows Server 2003 or Windows server 2008. Migrating the application layer through compatible means may be a way of alleviating exposure.

Third, which custom applications are on Windows Server 2003?

Last, you may be running Line of Business (LOB) or custom applications that require tight integration with a specific OS and require an environmental change (dare I say rewrite) in order to work in a modern environment. If you have an app that is tied to an OS, one of two things must happen:

  1. The application needs to be tricked in to thinking is living in a compatible environment.
  2. The application must be remediated, or altered to accommodate a new host OS.

Next Steps and New Options for Windows Server 2003 EOS

The standard next step used to be to upgrade. Pretty simple. The classic questions are: Do I skip a version altogether? Do I upgrade to the next version? Do I wait until the first Service Pack? While an upgrade is still an option for some workloads, the upgrade choices have increased exponentially.

Since 2003, a lot has changed. With solutions like cloud, private cloud and the ‘As-A-Service’ moniker for services like Platform As-A-Service (PaaS), Infrastrcuture-As-A-Service (IaaS), and Software-As-A-Service (SaaS), there are lists of choices for your Windows Server 2003 upgrade path.

Parts 2-5 of this post series will address some of the larger categories of options in the Microsoft space that IT organizations will choose from. We’ll also take a look at the positives, the negatives, upside and downside of each. Stay tuned!

In the meantime, visit our Windows Server 2003 web page where you can browse our services and read our report with Gartner called Make Migration From Windows Server 2003 a Priority, Before Support Ends in July 2015.

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