By Gordon Grosse, Technical Services Manager at Maindec Group

Windows Server 2003/R2 support finally finishes in July. With an estimated 23.8 million instances of Windows Server 2003 being used last year, this cessation presents a major challenge for organisations of all sizes. For users of this software, there will be an obvious business impact – with no more updates or patches from Microsoft, which can result in a less stable and secure infrastructure. Here are some facts highlighting what end of support means for users and recommendations for new alternatives.

No updates

Microsoft will no longer develop or release any updates after ending support. To put this in perspective—37 critical updates were released in 2013 for Windows Server 2003/R2 under extended support.

Compliance risks

After support ends, your organisation will likely fail to meet most industry-wide compliance standards and regulations. This could result in lost business or dramatically increase the cost of doing business, in the form of high transaction fees and penalties.

Zero savings

The costs of maintaining your legacy servers can add up quickly. Maintenance costs for aging hardware will likely increase, and you will have to deal with added costs for intrusion detection systems, more advanced firewalls, and network segmentation—all simply to isolate 2003 servers.

No safety

Without continued support from Microsoft, your virtualized and physical instances of Windows Server 2003/R2 will not pass a compliance audit. Microsoft Small Business Server 2003 will also be affected.

Action stations

With end of support, you essentially have three options to consider. You can do nothing, which will leave software unsupported without patches and security updates, choose to upgrade your server and then move some components to the cloud, or move completely to the cloud.

For the cloud options, optimistic estimates for migrating a workload off Windows Server 2003 is 150 days, approximately 30 – 60 for the operating systems, and 90 days for the application/workload. However, this process could take longer, and depending on the number of migrations, taking action now is a sound option.

Your migration should ideally follow a process to make the transition from Windows Server 2003/R2 to the cloud as smooth as possible. That process will include discovering, assessing, and targeting workloads and software, before choosing the right migration plan.

Here are some recommended steps to achieve this.

Step 1 - discover and catalogue

The first step is to discover and catalogue all of the software and workloads running on Windows Server 2003/R2. There are several self-service tools that can help with this process, such as the Microsoft Assessment and Planning (MAP) Toolkit - a free tool that helps you collect and organise system-wide information from a single, networked computer.

You can also try other third-party discovery offerings include Dell ChangeBASE, Lakeside Software SysTrack, JumpStart for Windows Server 2003 from Microsoft Services, and a number of other options from system integrators and Microsoft partner service providers.

Step 2 - assess

Once you have a catalogue, you will need to assess what’s in it. This means categorising and analysing your catalogued applications and workloads based on type, criticality, complexity, and risk. After completing your assessment, to help identify issues and opportunities, you can prioritise workloads and applications for migration.

Step 3 - target

Choose a migration destination for each application and workload. Available options include Windows Server 2012 R2, Windows Azure, Cloud OS Network, and Office 365. Different workloads and applications will logically lead to certain targets. Others could offer the possibility of migration to one or more of these destinations. The choice will be driven by factors such as speed, ease of migration, cost, and desired functionality.

Step 4 - migrate

Choosing the right migration plan may require some additional analysis and assistance. Several vendors offer do-it-yourself tools to assist in the decision-making process and in the migration itself, including Dell ChangeBASE, Citrix AppDNA, AppZero, and JumpStart for Windows Server 2003. Other migration services are also available through system integrators, including several Microsoft partners.


Windows Server 2003 end of support will present challenges – especially by not taking action. However it also provides a great opportunity to look at the future, and modernize your IT infrastructure to generate greater cost savings – as well as increased efficiencies.