Addressing Windows Server 2003 Migration Uncertainty

In 2003, I was a strapping 14 year old entering the 9th grade. The original XBOX was just catching its stride. Camera phones we’re quickly becoming popular. Windows Server 2003 was introduced by Microsoft. On July 14, 2015, Microsoft ended support for Windows Server 2003. There are some very serious consequences if you’re not started your Windows Server 2003 migration to newer operating systems. This post will address a few of the common questions surrounding said consequences.


So what does it mean to be unsupported?

Should the term “end of support” be unclear, IDC have provided a whitepaper providing a long list of concerns on why your organization should migrate off Windows Server 2003. Here are some of the many reasons  but these were the ones that resonated with me.

  1. Elimination of security fixes
    No more patches? For a second that almost sounds like a good thing, right? You’re probably tired of patching servers. But, think of the consequences and implications of that. No more patches is a terrible, scary, awful thing. If I need to tell you why, you may consider a different career than the one that brought you to my blog. If you ever want to pass another audit, you better be receiving and applying security fixes for all your products, especially ones as fundamental as your Windows OSes.
  2. Lack of support
    Have you ever called Premier Support? Read TechNet blogs or forums? Microsoft is shutting down support for Windows Server 2003 once it hits end of life. If you want help upgrading, you better get it now because after the end of life date, it might be a challenge to get.
    Saying “I can put this off, I’m just going to buy extended support!” is the wrong attitude to have. First, you could buy an Egyptian pyramid for the amount of money that extended support is going to cost. Second, all you’re doing is delaying the inevitable. You have to do this. Do it now. It’s going to hurt more to put it off and do it later.


Upgrading is so intimidating. I need help! Where can I get some?

Microsoft provides many resources to get you started and your organization started in planning your migration:

  1. Microsoft Virtual Academy
         - Windows Server 2003 End of Support Migration Overview
         - Migrating to Windows Server 2012 Training
         - How to Assess Your Windows Server 2003 Environment
  2. CANITPRO.NET – There are many great posts available. Top choices include:
         - Step-By-Step: Active Directory Migration from Windows Server 2003 to Windows Server 2012 R2
         - Step-By-Step: Migrating a 2003 file server with Microsoft File Server Migration Toolkit
         - 20 Helpful Steps Migrating Windows Server 2003 to 2012 R2
  3. Microsoft Migration Planning Assistant – Assists in migration planning covering Discovering, Assessing, Targeting and Migrating


I get it. I want to upgrade. I’ve been pushing my organization to upgrade but I can’t seem to get permission. What can I do?

While the arguments stated above make sense for an IT Professional, it might not resonate with executives, business people, or sometimes even developers. Here are a few of the common ways I see resistance and my suggestions to overcoming them.

  • App XYZ only runs on Windows Server 2003 and is crucial to our business. There is also no new version.

Respectfully, if this is the honest to goodness truth for your organization, you might be on the Blockbuster/Kodak path of sustainability. Read this Wikipedia article on the theory of Diffusion of Innovations. Take special note of chart that describes the different stages: Innovators, Early Adopters, Early Majority, Late Majority, and Laggards. You don’t have to adopt every new innovation that comes across your desk, but if your entire business is dependent on a technology or product that is about to reach end of life, you’re in trouble. You’re already in the laggard stage of the adoption process if you’re still not off Windows Server 2003. Just don’t fall off the chart completely – get migrating!

  • App XYZ is crucial to our business. A new version is available but we can’t afford the down time to upgrade.

This one is easier to work with than the last one. Attack this resistance from two sides. First, reiterate the importance of upgrading and all the bad things that will happen if you don’t. Second, and most importantly, find business reasons that make migrating to Windows Server 2012 R2 or the new version of App XYZ desirable to your specific stakeholders. Often with executives and business groups, it’s even more important to PULL them towards something new as it is to PUSH them away from something old.

To address the downtime concerns, put effort into making a plan that makes the downtime as short and painless as possible. Do a side-by-side migration. Do the cut over at 3 in the morning when your customers are all asleep. Find a way to make the downtime as tolerable as possible.

  • We don’t need new features. We accept the risk of running in an unsupported fashion. It’s just not worth our time to migrate.

This is a naive attitude, in my opinion. If you can’t find a creative way to improve anythingwithin your organization with even one new feature in Windows Server 2012 R2, you’re not looking. A willingness to accept the risk of running unsupported demonstrates a lack of complete understanding of the risk involved with doing so. What would your customers say if you told them that your systems don’t receive security updates any more? If you get resistance like this, you need to find a reason to pull your stakeholders towards the newer technologies and make sure they’re clear on the risks of maintaining status quo.

If you take anything out of this post, make it these few things.
  1. Being unsupported is bad. Really bad. You don’t want to be unsupported for a lot of reasons including no more security patches.
  2. Windows Server 2012 R2 has a ton of new features that make it a great OS to migrate to.
  3. Microsoft has a lot of resources available to help you upgrade.
  4. Getting stakeholder permission for an upgrade is as much about selling the benefits of moving to a new system as much as it is about the disadvantages of staying on the old one.

Good luck and happy migrating!

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