Be Prepared to Close the Book on Windows Server 2003

There’s something big coming on July 14, and your small business may need to prepare for it. We’re not talking about Bastille Day. Rather, July 14th 2015 is the day Microsoft finally ends support for Windows Server 2003, which means the company will stop issuing security patches or providing technical assistance for any version of Windows Server 2003 (W2K3), which we should note includes Small Business Server (SBS) 2003.

We’ve been down a similar road recently, as Microsoft pulled the plug on the aged Windows XP operating system just under a year ago. But there’s more at stake with Windows Server 2003 than just some desktop or laptop PCs, because servers can house data, applications, and services that are critical to running your entire business.

Unfortunately, getting a W2K3 server up-to-date isn’t as nearly as simple as inserting the latest version of the operating system and clicking an “Upgrade” button. In many cases it will require a migration process of variable—but often considerable—length and complexity to find your affected servers, identify what software components (a.k.a “workloads”) they contain, determine where they can be relocated, and then do the actual transfer.

Microsoft dubs this four-step process Discover, Assess, Target, and Migrate, and with barely five months to go before the deadline (which Microsoft announced more than two years ago) there’s not much time left to get it all done.

Prepare for the end of Windows Server 2003

The End (of Windows Server 2003) is Nigh

Of course, W2K3 isn’t going to suddenly stop working come mid-July, and given the potential time and effort a migration may require, you may be tempted to succumb to inertia and ride things out with the status quo. (Case in point: nearly a year after its sunset date, Windows XP still has nearly 20 percent of the desktop operating system market according to NetMarketShare).

But sticking with W2K3 would be a mistake. Here are three reasons why you should show it the door as soon as possible.

1. Security and Compliance

Once the security patches stop coming, any known or yet-to-be-discovered security flaws in W2K3 will remain vulnerabilities indefinitely.  Even if your W2K3 servers don’t directly touch the Internet (e.g. such as Web or remote access servers), they can still put your network at risk.

If you think there’s nothing left to patch in such an old OS, think again—Microsoft issued 37 critical updates for W2K3 in 2013. Moreover, if your business is governed by regulations such as PCI DSS or HIPAA) use of obsolete server software almost certainly means you’re no longer compliant with their requirements.

2. Third-party Support

Got any third-party hardware or software currently running on W2K3 servers, or planning to get anything new? Once Microsoft stops supporting W2K3, you can bet most other hardware and software vendors will as well—assuming they haven’t already.

3. Performance and Productivity

W2K3 is nearly a dozen years old, and technology has come a very long way since if first debuted. For example, the most common Standard and Small Business flavors of Windows Server 2003 allow only a mere 4 GB of RAM, which is less than you’ll find in most modern desktops or laptops. By comparison, the current Windows Server 2012 R2 supports 32 GB to 4 TB depending on version, and this opens the door to better performance and more sophisticated capabilities.

The W2K3 Migration: A Four-step Program

1. Discover—What do you have?

If you’re a one-server business, this question shouldn’t be tough to answer. But if you run several servers, it pays to check out the Microsoft Assessment and Planning Toolkit. It will inventory and analyze the server hardware and software it finds on your network. And it produces a Legacy Windows Server Inventory Report telling you what services and applications are running on W2K3 systems.

2. Assess—What does it do?

Broadly speaking, your discovery process will uncover items that fall into one of four categories—server roles (such as an Active Directory domain controller, remote access server, DNS, DHCP, etc.), Microsoft applications (Exchange mail server, SQL databases), third-party applications, and in some cases, custom applications (e.g., those developed specifically for your organization).

From here, the next step is to categorize what you’ve discovered according to how significant each item is to your business operations—is an item mission-critical (your business ceases without it) or merely important? You may also find items that are candidates for retirement, either because they’re redundant or just not used enough to justify the migration effort.

Part of this assessment includes determining how complicated the migration for a given application or service will likely be and how much (if any) downtime your business can tolerate during the process. If the answers are “very” and “not much,” respectively, then prioritize them since they’ll demand more time and resources.

3. Target—Where can it go?

Once you’ve categorized and prioritized, it’s time to determine the best destination for each one of your applications and services. Windows Server 2012 R2 (the current version, as the next one isn’t due for release until 2016) is a logical place to start, and beginning fresh with new server software (and hardware—don’t even attempt running new software on old hardware) is a relatively straightforward route.

But this is also an opportunity to consider transitioning into new technologies that can be more efficient and cost effective, such running your server(s) on virtual machines rather than directly on physical hardware. For example, Microsoft’s Hyper-V virtualization platform is built into Windows Server 2012 R2 (VMWare and Citrix also offer virtualization technology). You might even consider virtualizing existing WK23 servers as a stopgap to help smooth the transition; the excellent (and free) Windows Sysinternals Disk2VHD tool is one way to accomplish this.

Migrating away from W2K3 is also a chance to go (at least partially) from having all of your computing resources on-premises to hosting them in the cloud. Options here include Microsoft’s own Azure platform, Amazon, and countless others. Cloud options can also include Office 365 for things like email, calendar, and online meetings, and lest we be too Microsoft-centric here, don’t forget Google Apps.

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4. Migrate—The Hard(est) Part

After you complete all the research legwork, it’s time to start the heavy lifting that migration entails. But you need not go it alone. Assuming you don’t have an internal IT staff or external support provider to turn to, other resources are available to assist.

For its part, Microsoft’s offers extensive online resources that delve into each aspect of the migration process in considerable detail. One useful tool in particular is the company’s Windows Server 2003 Migration Planning Assistant, a wizard that walks you through possible migration options based on information you provide about your company and its W2K3 resources. Another is this detailed overview of the migration process (PDF link).

But Microsoft isn’t the only game in town; various third-party vendors, including AppZero and Nutanix offer products and services to help ease the migration of servers and applications. Information about other migration tools and method (both free and paid) is available courtesy of SpiceWorks. In fact, SpiceWorks maintains an extensive Windows Server 2003 End of Life forum with links to discussions, guides, videos, etc.

Finally, depending on how many “bodies” you uncover, the migration could take many weeks, months, or quarters, and you may not make the July 14th deadline. That’s not ideal, but it’s OK, provided you get the ball rolling now.

Joseph Moran is a veteran technology writer and co-author of Getting StartED with Windows 7, from Friends of ED.

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