Windows Server 2003 Support on Microsoft Azure

Windows Server 2003 Support on Azure

In this blog post, we will look at Windows Server 2003 Support on Microsoft Azure public cloud.

My Intent for writing this post is to give a deeper view to all organizations considering migrating their existing on-premises Windows Server 2003 workloads to Microsoft Azure as an aftermath of Windows Server 2003 End of Support (EOS) in July 2015.


“Can We migrate our existing Windows Server 2003 based Workloads to Microsoft Azure?” This has been one of the most common questions asked from me by many customers, especially too much over the last couple years. And not only from me, but this question would have been asked umpteen times from every consultant helping customers envision / plan /migrate their existing on-premises Windows server based workloads to Azure.

The primary basis for this frequently asked question stems from a popular misconception that Microsoft does not support Windows Server 2003 on Azure, which is not exactly completely True.

Let’s explore a bit of background story around Windows Server 2003 support from Microsoft in general, before we look at what level of support this particular Server OS version has on Microsoft Azure. It is important for you to understand the overall picture in this regards, before your Organization/Customers can make an informed decision around whether you can consider moving your existing Windows Server 2003 workloads to Azure or not.

Background Story:

Its 2017 now, and am sure you already know that extended support for Windows Server 2003 from Microsoft ended on July 15th, 2015. This was exactly 1.5 years back from now.

The mainstream support for Windows Server 2003 had already ended much earlier in July 2010. However, after a huge hue & cry from customers WW, Microsoft decided to provide the extended support till July 2015.

What does an OS End of Support (EOS) mean in Microsoft terms? It means that Microsoft will no longer issue security updates / patches for the concerned OS (Windows 2003), and no custom/application support will be offered anymore for the Server OS platform.

Windows Server 2003 End of Support
Windows Server 2003 End of Support

What are the possible consequences if you do not upgrade? All industries have to meet one or many regulatory (PCI, HIPAA, SOX…) requirements to conduct business. No support from Microsoft for Windows Server 2003 will lead to regulatory compliance failure for Industries continuing to run their business workloads on Windows Server 2003. This will hamper their ability to do any kind of business with compliant businesses, and would a major Issue. Also, no continued support from the platform vendor would introduce the risk of exposing the existing business workloads to online security threats.

Wait! You can still get some form of support from Microsoft for Windows Server 2003: Microsoft also announced that they will only offer custom support to those customers who have a committed plan to migrate their Windows 2003 deployments in the near future. This kind of support can be obtained by entering into a Custom Support Agreement (CSA) with Microsoft, and is very expensive. Obviously this would not be a workable option for most customers, purely from a cost perspective, unless the underlying scenario is desperate.

What Options are there to Upgrade from Windows Server 2003?

Following are the two most popular and common options for upgrading Windows Server 2003 based workloads, recommended by Microsoft because of the Windows Server 2003 EOS:

  1. Migrate to On-premises Windows Server 2012/R2 platform
  2. Migrate to Windows Server 2012/R2 platform on Microsoft Azure Public Cloud

In the context of this post, we are focusing primarily around migrating existing Windows Server 2003 workloads to Azure. Our Interest here is to discover if we have to mandatorily upgrade our existing Windows Server 2003 workloads to a newer Server OS for migration to Azure, or if we can move them as-is.

Does Azure currently support Windows Server 2003, or did it ever before?

Microsoft Azure never offered complete native support for Windows Server 2003 since the very time Azure IaaS came out. Neither does it support the same now. This was intentional right from the very beginning, and a part of their vision and strategy roadmap.

Do we really need to Upgrade from Windows Server 2003 for moving to Azure? Don’t we have any workarounds?

We do have another option for migrating the Windows Server 2003 workloads as-is to Microsoft Azure, which Microsoft neither recommends nor endorses anywhere. With this option, you would not need to upgrade from Windows Server 2003 as such. However, exercising this option will come with the obvious risks, and lack of support that Microsoft cautions about. We will have a look at this third option at the end of this blog post.

Current Reality:

Microsoft would would want us to believe that Windows Server 2003 EOS announcement resonated very well with all concerned Industries/businesses WW. However, ground reality is very different from what is being projected by Microsoft.

Microsoft obviously wants all businesses to Immediately upgrade to their latest and greatest OS/Software releases as soon they come out. This stance tremendously benefits Microsoft in terms of licensing profits, and pushing new Server OS and Azure adoption. However, such an expectation is completely impractical from a business standpoint.

Any upgrades to existing platforms/software, on which current business workloads are based, are dependent on a number of critical factors. Some of the top factors are like the overall cost of upgrade across all workloads, existing Application compatibility on the new platform, amount of time investment required, Application migration feasibility, business continuity etc.

Furthermore, many independent IT experts also cite no shattering or compelling reasons for businesses to upgrade on an Immediate basis. They debunk most of the reasons given by Microsoft for pushing the upgrade as simply holding no major concerns as such as of now.

Following points depict the current landscape of businesses, with respect to Windows Server 2003 EOS and Upgrade scenario:

  • Large number of businesses did completely upgrade their business workloads platform eventually, before/after the Windows Server 2003 EOS date. They either upgraded on-premises, or moved their business workloads to Azure, on newer Server OS platform (Windows Server 2012/R2, Windows Server 2008/R2)
  • Though a comparatively smaller segment than those who upgraded, but relatively significant number of businesses did not bother to at all upgrade their Windows Server 2003 based workloads either on-premises or move them to Microsoft Azure. These businesses continue to hold on with their decision on not to upgrade
  • There are still a large number of businesses, who only partially upgraded a part of their business workloads from Windows Server 2003. These businesses have at least one or more Windows Server 2003 based workloads deployed in their existing on-premises Infrastructures. This is evident from a 2016 report from Spiceworks, where they noted based on ther findings that more than half (53%) of companies all over the world have at least one instance of Windows Server 2003
  • A sizable section of businesses are still underway upgrading their existing business workloads from Windows Server 2003, either upgrading within on-premises, or moving to Azure. These businesses will get there, but take variable amount of time to completely/partially upgrade

Windows Server 2003 Support on Microsoft Azure:

Microsoft has published following official statement around Windows Server 2003 support on Azure. This is hidden away in an excerpt within Microsoft Knowledgebase article – KB2721672.

Windows Server 2003 and later versions are supported for deployment in Microsoft Azure. For versions that are earlier than Windows Server 2008 R2, there is no Azure Marketplace support, and customers must provide their own images. The ability to deploy an operating system on Microsoft Azure is independent of the support status of the operating system. Microsoft does not support operating systems that are past their End of Support date without a Custom Support Agreement (CSA). For example, Windows Server 2003/2003 R2 is no longer supported without a CSA.

What this simply means that “Microsoft does support Windows Server 2003 for deployment on Azure”.

However, Microsoft does not provide Azure Marketplace support  for Windows Server 2003. This means that there are no Windows Server 2003 Images provided by Microsoft (or any 3rd parties) in the Azure Marketplace. Customers have to use their own licensed Windows Server 2003 Images, prepared on-premises as a specialized VHD (not Generalized/Syspreped VHD), for deployment within Azure.

The above mentioned statement is an intentional strategy choice from Microsoft. They clearly do not want to encourage customers staying with Windows Server 2003, whatsoever be the reason, and want them to move to the newer Server OS platform.

You may now wonder that what happens to the Windows Server 2003 deployment support on Azure, given that Windows Server 2003 End of Support (EOS) already came into effect from July 15th, 2015. Understand that OS Deployment Support in Azure is completely different and Independent from OS Support from Microsoft. While Windows Server 2003 may no longer be supported by Microsoft from an OS perspective, its deployment support on Azure is absolutely valid and applicable.

You can also find a bunch of FAQ’s answered by Microsoft around running Windows Server 2003 on Azure here.

I have personally helped quite a few number of customers move their Windows Server 2003 workloads to Azure as-is in near past, without any Server OS upgrades for migration. Fortunately, I have not yet come across any negative Issues occur on these workloads, because of either lack of support from Microsoft (due to Windows Server 2003 EOS) or any Azure related issues specific to Windows Server 2003.

Hope you found this blog post useful. If you have any queries/feedback, please feel free to mention in the comments section below.


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