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Windows Server 2003 migration: it's all about the apps

  • Posted on February 19, 2015

Windows Server 2003 EOLJuly 14, 2015, is fast approaching and with it comes the latest challenge in our lives as infrastructure consultants. The big question: How do we help our customers move away from the mind-boggling number of soon to be out-of-support Windows 2003 servers to a current, supported OS platform? Statistics place that number in the tens of thousands that currently form a large chunk of server environments. It is vital that our customers and everyone else impacted by this challenge understand and acknowledge that retiring their Windows 2003 servers is not a standard data centre / server migration exercise.

The time is NOW to start on this migration journey. In fact, the U.S. Department of Homeland Security issued an alert saying IT departments running unsupported software could open businesses up to elevated cybersecurity risks.

Windows Server 2003 has been around for many years and for many organisations it became a core platform on which they have deployed the majority of their line of business applications and infrastructure services.  Therefore, to successfully phase out Windows Server 2003 on any customer's server estate, the focus should be on the applications running on those servers, rather than just the servers themselves.

A successful Windows Server 2003 migration is guaranteed to be a complicated effort, involving many skilled teams and several man hours of effort. However, a few key pointers can make the eventual migration / re-platforming go a lot smoother:

Understand the Target Environments

  • Landing criteria need to be clearly defined for the target environment(s) to which apps and services will be migrated (aligned with the customer's IT strategy)

Conduct Top-down Business Engagement

  • IT leadership must propagate the right message to their management and ops teams to make sure they understand the benefits of, and are ready to participate in the change.
  • This helps make future lower level engagements run a lot smoother

Application Discovery & Deep Analysis

  • Every business application / infrastructure service instance and the servers on which they run (along with key technical contacts) must be identified and a single source of truth created and signed off
  • In parallel to discovery, each application must be assessed from several angles (compatibility, architecture, security, data model, business requirements etc.) to understand its dependency on other apps, software and services.
  • The output of this analysis will help determine complexity of migrating an application or service.

Decide Migration PathsBased on the output of the app analysis, decisions must be made on whether each application:

  • Is suitable for re-deployment as-is to the target platform(s)
  • Requires re-architecting / re-engineering / a new version in order to be re-deployed to the target platform(s)
  • Cannot be moved / needs to be retired

Pilot Migrations

  • A number of low risk / non production apps with different levels of complexity should be identified and used to assess technical and administrative effort (and associated cost) for a "typical" app migration

As part of a larger migration program, these activities will go a long way in ensuring that Infrastructure and Application teams work hand in hand to plan and execute application migrations, eventually eliminating Windows 2003 Server from their environment.  I have found that following these best practices have saved invaluable time in the migrations I have done with clients. I hope that in sharing this information, it can aid your migration as well. You may also want to visit the Microsoft Windows Server 2003 Migration website and Avanade Application Modernization Services for additional insights. I've also pasted our brochure below that offers more information on how we can accelerate your Windows Server 2003 transformation.

I welcome a chance to hear how your migration journey is going? What is the #1 tip you would recommend?

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