Upgrading Windows Server 2003: The procrastinator's guide

Considerations for getting started.

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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.

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