Ah 2003. George W. Bush was president, 50 Cent was topping the charts and Microsoft rolled out Windows Server 2003.

On July 14, though, the product’s long run will end as Microsoft yanks support.

Many people will be surprised it took this long. The install base for the product, however, is 11.9 million, according to Microsoft. “The numbers are absolutely astounding, especially when one considers the fact that businesses and CIOs are well aware of the imminent end of support,” the company wrote in a blog post in February. The post noted that despite alerts from the U.S. Department of Homeland Security “organizations are simply not moving off the platform quickly enough.”

For some, this will sound very familiar. Microsoft ended Windows XP extended support in April 2014 even though many people were still using the product.

Microsoft’s rationale for ending support for Windows 2003 Server is logical enough: The product is more than a decade old. A lot has changed in the business world in that time. You wouldn’t expect a company to support, say, a smartphone that was so long in the tooth, would you?

Nevertheless, not all IT managers sympathize with Microsoft’s plight. On this Reddit thread several complain about the fact that their management has been resistant to spending money on an upgrade and the switchover will now be a mini mid-summer crisis, even though there’s been a lot of time to prepare for it.

Even when management is on board, it’s still a headache. As one noted, “I’m not sure if I’m blessed or cursed, our management cares very much about getting everything off 2003, they just don’t care enough to understand legacy – certain legacy apps don’t run on 2008, the originating business that made the software is no longer in business, or refuse to pay for support contracts on some of these legacy applications.”

To help smooth over the inevitable bumps, Microsoft has set up this website with live chat. The site links to a Migration Planning Assistant page that is designed to guide IT workers through the process.

In short, the first step is to discover what’s actually running Windows Server 2003 on your data center. Then you have to assess which apps are “critical, complicated, depreciated and risky.” After that, you need to target where you’ll move, migrate or “reinvent” those workloads. Finally, you can migrate them and “enjoy the benefits.”

Benefits? Yes, Microsoft promises lots of benefits. An IDC report (sponsored by Microsoft and available as a PDF on the Migration Planning Assistant site, so make of it what you will) makes a case that Windows Server 2012 R2, the suggested upgrade, “offers relatively good application compatibility with Windows Server 2003.”

Windows Server 2012 also offers a “lengthy list of improvements compared with Windows Server 2003” that includes better security, extensive scalability, new operational roles and script execution capabilities.

To help convince the top brass, Microsoft also offers a Gartner-penned report (free with registration) with advice about how to make your case. (For example: Write a position paper that lays out your case for migration.)

Of course, with the changeover now about a month away, a position paper might not be feasible. For those who are still struggling to convey the urgency of the matter, the most compelling argument won’t be done via PowerPoint, but instead on Outlook’s calendar feature.