Preparing for your Windows Server upgrade

It's time to say goodbye to Windows Server 2003. Getting through the migration requires not just Windows expertise, but discrete knowledge of a company's business applications

This vendor-written tech primer has been edited by Network World to eliminate product promotion, but readers should note it will likely favor the submitter's approach.

f you've been clinging to Windows Server 2003 trying to ignore the fact that Microsoft will officially end support July 14, 2015, you're playing with fire. One the updates stop, you'll be exposed to troubling security and compliance risks. Take note that in 2013 alone, 37 updates were issued by Microsoft for Windows Server 2003/R2.

Yet upgrading servers is a resource challenge as well as a mindset issue. The top barrier for migration, according to a survey, is the belief that existing systems are working just fine, and many users worry about software incompatibility.

The actual migration process to Windows Server 2008 or 2012 (the likely choices) is straightforward and well-documented, and most Windows engineers can easily learn how to work in a new OS. The complexity lies in determining if and how business applications will successfully transition to the new platform, and which ones will need to be replaced or shuttered.

Some IT shops will find they simply don't have time to undergo this rigorous process. External service providers can help. Even if you have a sizable IT staff, you'll need to consider whether it's a worthwhile use of a senior engineer's time to work on server migrations, compared with other high-priority projects. Regardless of your approach internally or externally managed here are some steps for working through a successful move away from Windows Server 2003.

1. It is often surprising what midsize and large companies don't know about their internal IT systems. It's critical to identify how many servers you have, where they're located, and what OS and applications they're running. That gives insight into how many servers and which applications are at risk. Asset management software can help by updating this information continually, saving crucial time in the analysis. Don't forget to document what security systems are in place on servers, networks and applications.

2. It's important to work closely with business unit heads to communicate why and when the migration is happening and any expected changes to their applications. Determine what IT specialists you need (including database and application managers) and if you can free them up for the migration or if you'll need outside help.

3. Most companies will likely opt for Windows Server 2012, simply because it will last longer and it's the latest version. Yet whether this is feasible or not depends upon your applications. If a critical application or two aren't compatible with or don't have a near-term upgrade path to your desired OS, you've got the decision to replace it or retire it. Work closely with application vendors to understand if and when they will issue an updated version, keeping in mind that promises don't always pan out.

An application might also require running on a 32-bit version of the software. While both 2008 and 2012 offer 32-bit versions, this will cut performance. We've seen at least one case in which a company had to undergo two upgrades for a particular application from 2003 to 2008 and finally to 2012 because the application vendor was not ready for 2012. Knowing these factors ahead of time makes all the difference as you plan for migration.

4. A positive outcome of being forced into migration (other than getting a better and faster OS) is that it's the perfect time to push for a change in strategy. Most IT organizations will need to replace their hardware to install 2008 or 2012, yet there's also the question of whether your company should continue owning equipment at all. Companies of all sizes and sectors are looking harder at hosted and cloud environments, which reduces daily IT support for standard processes such as server maintenance. For those companies still worried about security and compliance, a co-location arrangement at a nearby data center can reduce some of the risk and cost of maintaining hardware on site. Managed services allows your staff to focus on initiatives that add real value to the business, rather than maintaining systems.

5. For a midsize to large company with dozens of servers and hundreds of applications, sorting out a migration plan can be overwhelming. Here's a simple way to look at it. First, you'll want to move any customer facing apps and public websites, since they present the greatest potential damage to your business if impaired or hacked. Next, begin the process of migrating applications with compatibility problems and which require customization or upgrades, as they'll take the longest time to prepare. In parallel, migrate the easy to move applications. These are the ones which are already primed to run on an upgraded operating system or can be upgraded quickly.

Technically, this is a straightforward process once you tackle all the previous challenges. However, server migration is not just a technical project. You'll need people to help with coordination and communication with the business, project management and support. You'll of course want to test the applications on the new servers before retiring the old ones. Backups are absolutely critical.

What if, despite your best efforts, you find yourself in no man's land, past the deadline, and your environment is still not fully transitioned to the new server platform? To mitigate security and reliability risks, ensure that all applications which are exposed to the Internet are fully encrypted and that all servers are also locked down. You'll need to invest more time monitoring applications that remain on 2003, watching for potential breaches or suspicious behavior.

If you've not already started on a Windows Server 2003 migration plan, don't wait another minute, but don't panic either. There's a world of experienced consultants and providers out there ready to help you complete a successful upgrade and keep your business running smoothly.

Abbett is Director of Advanced Technology Services at CentriLogic. He can be reached at:

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