Best Practices for Windows Server 2003 End-of-Support Migration: Part 2

We’re back with our 2nd blog post in the Windows Server 2003 End-of-Support (EOS) Best Practices series.  In today’s post we want to review the first activity that can help ensure a successful migration project – Discovery.  This activity allows you the opportunity to identify exactly what, and how many of your business critical applications are still running on Windows Server 2003.   To assist with streamlining your planning process, we’ve created this short video outlining the four step process to migration planning.

We recommend that each and every person on point for migration off of Windows Server 2003 takes part in an in-depth discovery to ensure that every application and workload currently reliant on Windows Server 2003 is identified.  We also recommend that even those of you who have already begun your journey to migrate off of Windows Server 2003, take a short moment to ask:

“Have we completed an in-depth discovery?” 

“Have we truly identified all Windows Server 2003 instances?”

“Do we have a list of each and every application, workload, and server role?” 

If you don’t have a strong (and confident) answer to these types of questions, then we suggest you do a more thorough investigation of your datacenter and application landscape.  You may be very surprised at what you find. 

Thorough discovery will assist you with clearly identifying ‘all’ locations that Windows Server 2003 can be running, and provide you with a crisper plan while ensuring compliance and security requirements are met.   For example, you may currently be running applications outside of your existing on-premises datacenter, or virtualized environments.  These types of environments are also at risk for creating compliance and security issues post July 14, 2015.  


Many companies and individuals who have completed a Discovery are surprised by the number of instances that are running, and the dependencies between workloads, applications, and the servers themselves. A well-executed discovery effort will ensure accurate project scope and efficient allocation of time and resources.  While identifying the true number of instances is a straight forward exercise, the benefits of completing this exercise as soon as possible, will provide you with a better opportunity to tackle the intricacies associated with migrating the applications themselves.  You’ll then be able to move forward with your Assessment and Rationalization of each application, database and dependencies.  The types of software and workloads that you’ll be discovering will fall into the following groups: 

  1. Windows Server Roles
  2.  Microsoft Applications
  3. Custom Applications
  4. Third-Party Applications

In addition to Windows Server 2003, you’ll also want to consider other technologies from the same era that your applications currently rely on.  I’m talking about your databases.  Applications that you’re running today on Windows Server 2003 will often have a dependency on data, and the associated database is most likely SQL Server 2005, which also reaches EOS 10 months (April 12, 2016) after Windows Server 2003.  As a result, your migration planning and Discovery has just expanded from discovering not only the number of Windows Server 2003 instances, but the number of SQL Server 2005 databases attached to each application currently supported by Windows Server 2003. 

Another thing to keep top of mind is that migration is not just confined to the Infrastructure IT function – but the developer function as well.  Most organizations find that they still maintain numerous custom applications, often developed in house, that have been running for the past 10 years. Making sure that your development teams are aware of your migration activities during the Discovery phase, will ensure they have an understanding around the impact of Windows Server 2003 migration and their role in supporting the migration of the identified applications to a supported operating system.   Reaching out to the development teams as soon as possible will assist with meeting timelines, but will also prompt the opportunity to take a hard look at these applications, in light of how much user requirements have changed over the last decade. 

Don’t take your foot off of the accelerator!  Each migration project will be unique, and the best way to ensure confidence and a strong plan is to conduct a true “Discovery” effort that includes every area of the business.  Your Microsoft representative, as well as Microsoft Consulting Services and Partners are here to assist.  Discovery and Immersion Workshops are available today, so that you can clearly identify your opportunities for modernization, and realize the benefits available with the latest generation of server innovation. 

Until our next post, we encourage you to reach out to your Microsoft Representative and Microsoft partners and to visit the Windows Server 2003 end-of-support website where you will find a number of additional resources to help your planning and decision-making. 

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