Windows Server 2003 End of Support: Your 4 Step Process for Migrating to a Modern Solution

November 4, 2014
Michael Grasso


Michael Grasso

Cloud Services Architect SoftwareONE Pennco Technology Institute High-Performance Technical Sales Professional with IT experience ranging from sales engineering, infrastructure engineering, datacenter management, consulting, strategy, and project management. Linkedin

Now that you’re aware of the upcoming end of support (EOS) for Windows Server 2003, it is time to address potential solutions for migrating off your expiring workload and onto a modern solution.

With 252 days remaining as of the date of this publish, SoftwareONE’s team of Microsoft Certified Professionals (MCP) have developed a simplified 4-step roadmap to help your IT team make the transition.

1.  Discover – Inventory Applications and Workloads

This hardly goes without saying, but uncovering your IT environment’s Windows Server 2003 footprint forms the vanguard of this process. Many customers are familiar with Microsoft’s annual True-Up, so this stage of the process shouldn’t be too alarming.

Microsoft provides many downloadable tools to help with Discovery. The Microsoft Assessment and Planning Toolkit (MAP) is a basic scanning and inventory tool to help discover what’s running in your network. However, if you’d like to obtain a more defined view of your inventory to help make better purchasing decisions over the course of 3 years as opposed to just the next 250 days, thenSoftwareONE offers several global leading services to accommodate your needs.


Software Asset Management (SAM) provides organizations with the capabilities to maximize investments and understand the complexities involved with software licensing. By comparing your Discovered inventory against publisher entitlements, SoftwareONE’s team of SAM Specialists create a GAP analysis to identify what you have versus what you own, allowing you to strategically remediate any “gaps” in licensing requirements.

2.  Assess – Categorize Applications and Workloads

Now that you’ve identified your Microsoft Windows Server 2003 footprint, the next step is to Assess those workloads into 3 categories:

By Type: Organize your apps based on their function.

  • Microsoft Server Roles
    • Where are your File and Print servers?
    • Where are your Remote Desktop servers (previously Terminal servers)?
    • Where are your Web servers?
  • Microsoft Applications
  • Microsoft Apps
    • SharePoint, Exchange, Lync, Office Communications Server (Live Communication Server for Windows Server 2003)
  • Customized (in-house) Applications
    • Custom Apps built in-house on the Microsoft platform
  • Third-party Applications
    • Any apps housed on Windows Server 2003 that is not a Microsoft product

By Criticality: Organize your applications based on their significance to business productivity.

  • Mission Critical
    • Essential to business continuity – must be targeted first
  • Important
    • Can be without for a short period of time
  • Marginal
    • These apps could survive an extended outage should there be complications
  • Can Be Retired
    • Which apps are being replaced by a more modern platform

By Risk and Complexity: “Risk” is defined as the time remaining that the publisher will provide support for the application.

  • High – Less than 12 months (Windows Server 2003)
  • Medium – 12 – 24 months (SQL Server 2005)
  • Low – 24 – 36 months (End of Mainstream Support for Windows Server 2008)


3.  Target – Evaluate Options for Each Application and Workload

Now that you have a solid assessment of your applications and platforms, the next step is to evaluate potential options. Support for Windows Server 2003 is ending, so alongside an OS upgrade, you will likely need to upgrade to modern hardware as well.

Windows Server 2008 R2 can integrate with certain cloud applications, but wasn’t designed for the cloud. Windows Server 2012 and R2, on the other hand, was built from the ground up to embrace the cloud, so organizations looking to “burst” into the cloud will be better off with Windows Server 2012/R2.

Furthermore, Windows Server 2008 R2 will undergo end of mainstream support January 2015, and go into extended support in 2020. Therefore Windows Server 2012/R2 is a better long-term strategy.

Many organizations are making the innovative decision to move to the cloud. Microsoft’s flagship cloud product – Microsoft Azure – achieves all of the Windows Server needs while eliminating the capex requirements for purchasing additional hardware as your business grows. In addition, operational expenditures are greatly reduced.


The graphic below demonstrates the various capabilities of cloud computing – everything in red is the responsibilities of the IT Administrator, while everything in grey represents the responsibility of the cloud service provider:


4.  Migrate

The final step in this process is to finally migrate your Assessed workloads onto your Targeted platforms. There are two primary, and relatively obvious, methods for migrating your applications – doing it yourself or employing outside services.


As mentioned above, one of the primary reasons for moving to the cloud is to free up IT resources. Many organizations are unable to allocate the necessary resources to do a seamless migration, so utilizing deployment services from a certified Microsoft Azure partner will alleviate any concerns of an improper installation.

End of support for Windows Server 2003 approaches, and the typical migration path can take between 200-300 days – with 250 days left, there’s no room for error!

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