Today is the day. As of July 14, 2015, Microsoft is ending its extended support for its very popular Windows Server 2003.

That means that Microsoft will no longer issue security updates for any version of this platform. The company warns on its website:

"If you are still running Windows Server 2003 in your datacenter, you need to take steps now to plan and execute a migration strategy to protect your infrastructure."

The hope, of course, is that these companies will migrate to Windows Server 2012 R2, Microsoft Azure or Office 365. Indeed there are several helpful migration links alongside Microsoft's warning.

And of course, tech media has examined the issue in depth.

As have tech industry analysts.

Change is Hard

To be sure, Windows Server 2012 R2 et al. are all very fine products  -- but Windows Server 2003 was popular. 

And migration, for any IT solution, can be tricky and involved. Windows Server 2003 appears to be no exception based on some of the issues discussed on the user forum dedicated to questions about Windows Server 2008 migration issues.

The upshot is that if you haven't made the jump for any of the above issues, you are not alone.

Some 21 percent of servers scanned in the first half 2015 are still running on Windows Server 2003 — down just 11 percent from the same period in 2014, according to Softchoice's TechCheck analysis of nearly 90,000 servers at more than 200 organizations.

The analysis also found just 7 percent of those organizations have fully migrated to newer operating systems and have no instances of the old server operating system in their environments, up from 3 percent in 2014.

Cyber Attacks Poised to Happen

This is a very dangerous state of affairs, according to Softchoice. Failing to upgrade will, among other things,  "result in serious business risk after July 14th when Microsoft is no longer providing support or security updates," said David Brisbois, Softchoice's senior manager of assessment and technology deployment services consulting.

Even the Department of Homeland Security has taken note, issuing an alert about the Microsoft ending security support for Windows Server 2003.

Besides the higher vulnerability to cyber attacks, DHS pointed out that users may have problems with software and hardware compatibility and any companies that must meet regulator obligations "may find they are no longer able to satisfy compliance requirements while running Windows Server 2003."

With even the DHS weighing in it is worthwhile asking, why on earth are so relatively few companies making the switch?

Costs of Migration vs. Better Performance

There are actually viable reasons, starting with the migration costs, Charles King, principal with Pund-IT told CMSWire.

"A sizeable number of upgrades will require hardware upgrades as well.  And depending on the IT use, a company might decide that the costs associated with the upgrade is not worth the better performance or better support for applications than what they are getting now."

It also may be that other IT projects are taking priority, he added.

As for the security issue that everyone is up in arms about … it is riskier not to migrate, he said — but Microsoft has gone to a great deal of trouble in general to increase its security overall.

"Businesses understand the dangers of unsecured systems and they typically install and manage multiple layers of security around data center assets," King noted.

The Virtualized Environment

There are other trends to consider as well in a virtualized environment, writes Krishna Raj Raja, a VMware expert on CloudPhysics' product development team, in a blog post.

He wondered: "Is Windows Server 2003's support end of life really that significant or is Microsoft just leveraging this event to persuade their users to migrate to the Microsoft cloud?"

It is a question, incidentally, that he never answers directly. But his big data-based analysis of the situation does school readers on the advantages of vSphere environments.

He writes:

"Why do people continue to run legacy OSes on vSphere environments? The short answer is: because they can.

"For example: Before virtualization, a server refresh generally required an OS refresh. Newer hardware platforms typically have limited or no support for legacy OSes so upgrading the OS became a necessity. With virtualization however the hardware and the OS is decoupled and therefore OS upgrades are not a necessity.

"VMware announced support for 64-bit OSes in 2004 and the vSphere platform supports running both 32-bit and 64-bit OSes simultaneously. There is no need to choose one over the other, legacy 32-bit OS (and even 16-bit OS) can continue to coexist with newer 64-bit OSes.

"VMware’s support for legacy OSes is excellent. It is possible to run a legacy OS like Windows NT on modern processors that Windows NT natively wouldn’t even recognize. Also the virtual devices in VMs provide encapsulation and prevent device driver compatibility issues."