With the impending death of Windows XP this month and Windows Server 2003 next year, it begs the question: When is it time to start planning the retirement of any remaining x86 hardware, as well as any virtual machines still running 32-bit Windows?

No doubt, by now many organizations have completely converted all of their server installations to x64 instances, but there are some who have not. For some organizations, access to even legacy x86 hardware can mean the difference between having another server instance in production or not, and virtualization also requires investment in additional 64-bit hardware. But now is the time to start developing a plan for retiring these systems.

To understand why, let’s first take a look at some of the considerations by operating system, and then by the roles that may be in use on those systems.

By Operating System

Windows Server 2003

Let’s start with the obvious consideration: Windows Server 2003 (WS2003) is slated for the end of Extended Support in July 2015, which is 15 months from now. In most cases, whatever you still have running on WS2003 will likely be functional on Windows Server 2008 (WS2008), but clearly it would be better to run that on Windows Server 2008 R2 (WS2008R2).

Either way, now is the time to start planning for migrating off of WS2003 systems, including the rare existence of a WS2003 x64 system. In July 2015, Microsoft will quit publishing security updates for WS2003, and as bad as a vulnerable desktop system can be (read: Windows XP next month), a vulnerable server is exponentially worse.

Windows 2000 Server

As much as it pains me to even say this, there are some organizations still using Windows 2000 Server in production environments as application servers for legacy applications. Hopefully, they’re at least running in virtual machines. If not, and you’re stuck with a legacy application that can’t run on a 64-bit operating system, maybe it’s time to seriously consider migrating the application instead.

Windows Server 2008

This version of Windows is the one that perhaps offers the most ambiguous perspective on the question. On one hand, WS2008 x86 systems are still in Mainstream Support (until January 2015), and will have security updates provided until January 2020, which may discourage a number of server administrators from lobbying for upgrades. But there are significant performance advantages in moving these systems to Windows Server 2008 R2 or Windows Server 2012. If it’s a question of server licensing costs, at a minimum consider moving these systems to WS2008 x64. Migrating to the 64-bit version can also facilitate getting off of 32-bit hardware as well.

By Role

Web Servers

Web applications running on IIS6 (WS2003) can generally be migrated to IIS7.5 (WS2008R2) as there’s full IIS6 emulation available on that platform. If you’re running web applications on WS2008 x86, give serious consideration to the performance advantages of moving that web environment to a 64-bit platform. Most notably, of course, will be the additional memory that can be provided to the Web applications.

File Servers

For file servers, you might want to go direct to Windows Server 2012 to get the benefits of SMB v3, particularly if those file transfers are occurring among other Windows 8 or Windows Server 2012 systems, or you’re interested in enhanced capabilities for file services clustering. But even if WS2012 is not in your immediate future, there are known performance advantages for file services on WS2008R2 over those on WS2003 or WS2008.

Active Directory

Active Directory is another reason for migration. If you still have any WS 2003 DCs, moving to a newer operating system will give you the opportunity to upgrade your domain and forest operational level, which provides additional features. Arguably, the most beneficial reason for killing off those WS2003 DCs is access to fine-grained password policies, which allow you to customize password policies for security groups or individual users. In a domain with a WS2003 DC, there is only one password policy and it applies to all users. In addition, if any of these WS2003 DCs are running in remote sites, there may be advantages by converting them to a read-only domain controller.

Whatever your particular situation, now is definitely the time to start planning for the safe retirement of 32-bit Windows systems, before the panic sets in a year from now.