10 Keys To Upgrading Windows Server 2003

Windows Server 2003 To-Do List

In less than four months the clock runs out on support for Windows Server 2003. That's when the end-of-life bogeyman is unleashed and IT admins need to start stressing about security, meeting legal and regulatory requirements, and encountering possible application failures related to running Windows Server 2003 after Microsoft stops supporting it.

The upshot to migrating off Windows Server 2003 is that there is a host of options that didn’t exist 10 years ago that can help bring new efficiencies to today’s modern workloads. Today’s options include more robust server virtualization, hosted cloud options, or a hardware refresh to something far more efficient.

For that reason, migrating can be a healthy kick in the pants to solution provider revenue and provide customers with a fresh approach to solving legacy business problems.

Here are 10 keys to migrating from Windows Server 2003 to Windows Server 2012.

Time Is Not On Your Side

In September 2014 there were roughly 20 million-plus instances of Windows Server 2003 facing an end-of-life support deadline of July 14, 2015, according to Al Gillen, program vice president of servers and system software at research firm IDC. Today that number is down to 7 million, he said. At the time of this writing, companies have just less than 100 days to migrate.

That’s a lot of migrations to complete and a deadline many companies will miss, Gillen said.

One out of three companies will miss the Windows Server 2003 end-of-life deadline, according to a survey of 500 enterprise businesses by security firm Bit9 Carbon Black. "With the critical role servers play at any enterprise, [Windows Server 2003] end-of-life presents an even greater risk than last year’s Windows XP end-of-life,’ the Bit9 Carbon Black report stated.

Taking Inventory

One key to an enterprise's migration path is knowing where it stands today.

That requires taking an inventory of exactly how many Windows Server 2003 systems an enterprise has on its network -- physical and virtual. That applies equally to software and the type of workloads that run on servers. Equally important is taking into consideration things such as dependencies on Active Directory, file content, settings and permissions.

Along with the hardware checklist enterprises need to catalog what other technologies are connected to the servers, such as storage and networking. Getting a handle on where a data center is today is an important first step in assessing where an enterprise needs to go tomorrow.

Hard Look At Hardware

Because hardware is central to migrating off Windows Server 2003, it's important to take a hard look at server profiles such as processors, memory specifications and excess storage space. It’s also important not to underplay the role hardware plays in migration even as IT moves toward a software-defined model.

"Unfortunately, some data center managers make the mistake of assuming that the enhanced intelligence of today’s platforms and operating systems (including Windows Server 2012 R2) somehow offsets the role of the hardware," according to a report by consultant Frost & Sullivan’s research arm Stratecast.

When it comes to upgrading hardware, low-cost commodity hardware isn’t always up to the task when it comes to running today’s workloads, according to Stratecast. "Even in a software-defined world, hardware is an essential component to computing and storage environments. ... Sophisticated infrastructure (servers, storage, and networks) is required to support optimal workload performance and efficient data center operations."

Does The Best Migration Option Include Migrating At All?

Once the hardware and software inventory is complete, then it’s time for the ultimate migration question:

Is the best migration option not migrating at all? Maybe Software-as-a-Service is the right fit for a customer.

Will a virtualized instance of Server 2012 R2 be robust enough for a customer’s workloads, such as analytics and collaboration tools that use high levels of processing power?

Migrating server applications to a virtual environment requires a full accounting of applications. First, consider what apps can be retired and replaced and then categorize them from critical to less critical.

What To Do About Mission-Critical Apps

Some vendors of mission-critical apps have either gone out of business or their apps are 32-bit and don't support Windows Server 2012.

Customers with mission-critical applications that are unsupported by Windows Server 2012 have options. Windows Server 2012 R2 offers a compatibility mode to run such applications, but it's not foolproof. The other option is reaching out to third-party app makers such as AppZero that will take applications, package them up, and make them a virtualized instance that can run on Windows Server 2012. Similarly, a firm called DH2i specializes in a container technology that enables workload portability for any Windows Server 2003 application or service.

But, as IDC’s Gillen points out, some applications unsupported by Windows Server 2012 are close to 10 years old and face their own end-of-life issues.

Putting Old Servers Out To Pasture

A Windows Server 2003 migration is liable to turn up some dead wood in the form of hardware that needs to be decommissioned. Take the opportunity to securely wipe local drives and take any unused and retired hardware off the books.

For borderline hardware, migration is the fork in the road for considering moving servers to the cloud. A thorough inventory of applications and hardware will help determine how many Windows Server 2012 instances might be transitioned to Microsoft Azure or Amazon Web Services.

Building A Better Network Architecture

At the heart of Windows Server 2012 R2 is Microsoft’s delivery of new features and enhancements in cloud, virtualization, management, storage, networking, virtual desktop infrastructure, access and information protection and a Web and application platform.

That said, any enterprise transitioning off Windows Server 2003 needs to be sure legacy storage and network infrastructures are ready to take advantage of Windows Server 2012’s streamlined management features designed to reduce total cost of ownership. The goal is to design the right infrastructure that allows reduced complexity, simplified management, lower costs, and speedier delivery of IT services for clients.

Keep The Trains Running

Making sure that any migration will have minimal impact on end users during consolidation is critical. That means factoring in things such as peak workload periods and performance demands for specific applications.

A recommended checklist includes:

-- Making sure stakeholders are aware the upgrade is taking place.

-- Identifying legacy software apps, discovering incompatibilities and being prepared to replace or fix line-of-business applications, middleware, database products and management tools.

-- Determining whether a staged migration is best.

-- Picking a date for migration that will least impact a business, including holidays, Memorial Day weekend and, worst-case scenario, the July 4th long weekend.

Software Tools

There are a number of key software tools that can help ease the pain of migrating Windows Server 2003 to Windows Server 2012.

AppZero offers what it calls "one-step" automation to Windows Server 2012.

Microsoft has a downloadable Assessment and Planning Toolkit.

Intel can help with coming up with the hard numbers argument for upgrading to Windows Server 2012 with a return on investment calculator available online.

Microsoft has released the Windows Server 2003 End of Service site, which contains a wealth of resources to help plan a migration.

Cost Of Doing Nothing

For the laggards, Microsoft sells after-retirement support contracts, called "Custom Support," with the caveat that those businesses must have a plan to totally eradicate the unsupported product.

The estimated cost of those extended support options start at $600 per server, per year, with costs escalating each year thereafter. Custom support is also limited to security patches rated by Microsoft at its highest level of "critical."

Postponing a Windows Server 2003 migration is just delaying the inevitable, and missing the deadline could have crippling consequences.

This is the first in a series of articles around Windows 2003 end-of-life issues.