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Preparing for your Windows Server upgrade

John Abbett, Director of Advanced Technology Services, CentriLogic | June 8, 2015
If 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.

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.

If 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.


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