With support for Windows Server 2003 and 2003 R2 ending in July 2015, it is important that organizations begin planning and preparing for an upgrade path that meets the unique needs of their business.  Organizations everywhere will need to begin assessing their current infrastructure and develop a strategy to migrate off the aging platform onto Windows Server 2012 R2 and Microsoft Azure.

Upgrading to a new operating system platform and moving its applications can often present a complex undertaking for organizations. Determining the approach that best meets the needs of the business is only the beginning of a challenging journey that could potentially introduce a lot of risk into the IT environment such as implementation failures and unexpected downtime.

To circumvent any unplanned surprises, we recommend a four-step approach in the Windows Server 2003 Assessment process:

  1. Discovery
  2. Assessment
  3. Rationalization
  4. Migration Planning

The initial engagement will typically take 3-5 weeks depending on the number of applications to discover and assess.  Once that has been done, the entity will have an inventory of all critical applications running on Windows Server 2003 servers, their potential complexity to migrate and their business criticality.

We then recommend that the enterprise engage in a deeper-dive rationalization and planning process. This will take more time than the initial engagement, because in this part of the process application owners and business teams need to be interviewed to gather finer details, particularly for those applications that are deemed very complex to migrate or of very high business criticality.


Through discovery, we can assist with targeting and reviewing existing server workloads and applications running on the aging platform to determine their readiness to move to Windows Server 2012 R2 and Microsoft Azure.


We utilize the Microsoft Assessment and Planning (MAP) Toolkit which is an agentless planning and assessment tool for quicker and easier server and cloud migrations.  This toolkit gathers detail on assets that reside within the current environment and provides detailed readiness assessment reports on each application’s compatibility with Windows Server 2012 R2 and Microsoft Azure, along with steps required to alleviate any compatibility issues.  At this stage, the inventory can be broken down by complexity to migrate and business criticality to help clarify which applications will be the focus of the following Rationalization step.


We will interview the primary stakeholders, application owners and business units to gather additional information about specific applications in preparation for migration planning, testing and remediation.

Migration Planning

We will work with you on developing a migration plan and roadmap in preparation of migrating the identified server workloads and applications to Windows Server 2012 R2 and Microsoft Azure.  We can further assist by putting your migration plan into action.

For more information about starting your Windows Server 2003 migration, visit CDW Windows Server 2003 End of Support, Start your Migration with CDW.