Upgrading Windows Server 2003: The procrastinator's guide

Considerations for getting started.

lifebuoy on wooden wall rescue overboard preserver saver

Windows Server 2003 support ends on July 15, as you may have heard. For some organizations -- mostly smaller or newer businesses -- this does not have any significance: They are most likely backing up to the cloud, using cloud-based apps and have a cloud-ready NAS on site.

But if you're part of a medium-sized company, especially with custom line-of-business applications, or a larger company with extensive investments in IT infrastructure, you probably have Windows Server 2003 machines all over the place. Although there were around 10 million Windows Server 2003 machines deployed at the beginning of 2015, best guesses from Gartner and Microsoft peg the number that will still run the old OS post-support deadline at between 2 million and 3 million.

Some of you may not be entirely sure what workloads those Windows Server 2003 machines are running, much less how you are going to forklift those applications and services over to a platform that is supported. If that applies to you, how will you cope with the end of support for Windows Server 2003? What are your most realistic options? We will discuss all of that.

Is this important?

Let us tackle the first issue up front: Is the end of support something to care about? From a pure technical-support standpoint, probably not. If you have been invested in Windows Server 2003 for this long, chances are you have institutional memory enough to solve Windows Server 2003 usage and troubleshooting problems, and failing that, the World Wide Web has plenty of historical information on problems and solutions for this platform.

Why you should care: Patches and updates for flaws and security holes will stop coming as of July 15. This means that there could be huge holes in Internet Explorer, or in the TCP/IP stack built into Windows Server 2003, or in the DLLs that Internet Information Services loads -- but none of those features and services will be protected against hackers looking to take advantage of flaws they find.

To continue reading this article register now

7 inconvenient truths about the hybrid work trend
Shop Tech Products at Amazon