Get Free Extended Security Updates for Windows Server 2012 R2 Before End of Support

Microsoft is providing a lifeline to Windows Server 2012 R2 users that are unable to migrate off at this time with free ESUs

Windows Server 2012 and Windows Server 2012 R2 will reach end of support on October 10, 2023. This means security updates, non-security updates, bug fixes, technical support, and online technical content updates will no longer be offered after this date. This puts some organizations in a difficult situation. Organizations with legacy applications may be unable to move to a modern server operating system. Those that have been dependent on Server 2012 R2 for published desktops also face a difficult migration as the Desktop Experience feature in Server 2016 and later is not as reflective of the Windows 10 and Windows 11 user interface, creating a jarring experience for end users. For these reasons and more, some customers may be unsure of how to handle a migration from Server 2012 R2. A lifeline has been offered to customers by Microsoft. Windows Server 2012 R2 customers can migrate applications and databases to Azure, including Azure Stack HCI, Virtual Machines, Dedicated Hosts etc. and receive Extended Security Updates for free.

This blog will highlight some of the options for handling the migration of EUC workloads from Windows Server 2012 R2 to supported operating systems.

Should You Migrate to a New Windows Server OS or Run Windows Server 2012 R2 in Azure?

When planning your migration, you should ask yourself: what operating system should I use? This question seems simple on the surface, but once you start evaluating your applications it gets complicated. Why are the applications still hosted on Server 2012 R2? Is it just a case of leaving your migration effort until now? If that is the case, you need to figure out what OS to move to and the applications could still dictate your decision. Maybe you wanted to migrate sooner but have applications that won’t work on the modern operating systems. Perhaps applications themselves are compatible but a prerequisite is not. It may be as simple as your published desktops were not working as well on newer operating systems and Windows Server 2012 R2 was a better fit from a resource utilization perspective. Whatever your reasoning or current situation during the planning of this migration is, you have a few possible migration paths (and challenges to address).

Windows Server 2012 Migration Paths

Migrate to Windows Server 2016

You may believe Windows Server 2016 is a logical next step as it was the next major version. It makes sense that most applications that worked on Server 2012 R2 should work on Server 2016. However, Server 2016 is already out of mainstream support and headed for end of extended support in 2027. If you choose to migrate to 2016 you will almost immediately need to start your migration from 2016 to a modern OS. Out of the box, Server 2016 is also more resource intensive than Server 2012 R2. If you choose 2016 you may try to migrate to 2016 and find the performance is unacceptable.

Migrate to Windows Server 2019

Windows Server 2019 is more resource intensive than Server 2012 R2 but can be less resource intensive than Server 2016. Server 2019 lacks some of the enhanced security features of Server 2022, but has lower resource utilization. If your choice is between Server 2019 or Server 2022 – and you are limited in available hardware for your hosts – this could steer you toward Server 2019. Of course, it is important to ensure your applications are compatible with the OS, which we will address later.

Windows Server 2019 is considered to be the Server OS counterpart to Windows 10. If you have been thinking you should move your published desktops to 2019 to provide users with a Windows 10 experience, you may discover you need to heavily customize the desktop appearance to align with the desktop OS. The reason for this, as alluded to earlier, is because the Desktop Experience feature in Windows Server no longer mirrors desktop operating system counterparts as closely as it did in the past.

Migrate to Windows Server 2022

At the time of writing this article, Server 2019 is the latest version available for Domain Function Level. If your infrastructure team already has the organization’s Domain Controllers running on Server 2019, you should be able to proceed with domain joining new Server 2022 machines. While more resource intensive than Server 2012 R2 and Server 2019, Server 2022 provides some significant new features.

If you use Hyper-V in your organization, there are several new features you can utilize, such as affinity and anti-affinity rules, VM clones, and live storage migration. There are also significant security improvements that make it more attractive, including TLS 1.3 being enabled by default, hypervisor-based code integrity, Secure-core server, and more. Windows updates handling has been improved, with the ability to update the OS in the background without requiring a reboot. There has been some storage enhancements such as file transfer speed improvements by compressing files on the fly, during transfer, and more!

As Server 2022 is the latest Server OS, it provides the longest duration of support available. This makes Server 2022 an attractive option, particularly for those who have ample hardware resources.

The elephant in the room here of course is your applications. You may want to migrate to Server 2022 (or even 2016 or 2019), but if applications don’t work on newer operating systems you may feel stuck on Server 2012 R2.

Migrate Windows Server 2012 R2 Machines to Azure

If applications cannot be migrated from Server 2012 R2, you may pay for Extended Security Updates (ESUs) to keep running your existing on-premises Server 2012 R2 servers and maintain business continuity.

Microsoft is providing an alternative. Organizations running Server 2012 R2 machines in their data center can get free ESUs if they move them to Azure as Azure Virtual Machines. Alternatively, you can continue running the servers on-premises using Azure Stack HCI and still get those free ESUs. This could provide the path of least resistance for some organizations. Regardless, the time is ticking on those ESUs. You still need to address the application problem and keeping the applications on Server 2012 R2 is not the optimal option for dealing with legacy application compatibility challenges.

Application containers can provide a solution for bringing legacy applications from Windows Server 2012 R2 to a modern Windows operating system. Application containers can be reused across Windows operating systems, ensuring your applications can seamlessly run no matter what your migration path is. They can actually help facilitate options that are currently not available to you with your current application stack, as well.

EUC Workloads

Legacy Applications

Do you have a solution to turn to, to run legacy applications on modern operating systems?  If not, this is something application containers can help with. Application containers can run with full isolation, meaning you can put deprecated OS components into the container and run them isolated from the underlying operating system, helping avoid conflicts while still presenting the required components to the applications that require them.

Application containers can also be set to run in a specific Windows compatibility mode, enabling applications to run in the compatibility mode of a Windows version the application will function with.

These help you expedite migrations from a Windows Server operating system to a desktop operating system, or from Server 2012 R2 to Server 2022 and beyond.

For more on how Cloudpaging application containers can help you with your legacy applications, check out our article here.

Published Desktops

If you have published desktops running on Server 2012 R2 due to incompatible applications, application containers can help as explained above. 

If you are in a situation where you would like to migrate applications to a multi-session operating system that provides a true desktop experience, you may consider using an Enterprise Virtual Desktop (EVD) image in Azure. A move to virtual desktops may be the de facto choice for most as Microsoft has outlined a change to Office 365 support, which will see it limited to desktop operating systems. EVD images which offer a multi-session desktop are available for both Windows 10 and Windows 11.

Unfortunately, you can expect significantly less user density than you got with your Windows Server 2012 R2 published desktops, but your desktops will be on an actual desktop OS which can make managing the machines easier.

The reusable nature of application containers makes it easy to lift and shift applications off your existing published desktops to a new virtual desktop. Moreover, you can remove applications from your desktop images and dynamically provision them directly to end users, giving you the mobility to move from on-premises to the cloud and from platform to platform with ease. It will also keep your image and desktop sizes smaller, leading to cost savings.

Published Applications

You may have published applications running on Server 2012 R2 session hosts. As stated earlier, the UI and other underlying differences in the modern server OS and desktop OS present a challenge for published desktops. Published applications, on the other hand, do not rely on the operating system UI as much. Publishing applications on Server 2022 is likely a good option going forward, unless the application needs to interact with a Microsoft Office product. In this case you may need to consider an alternative.

Similar to the published desktops use case, utilizing application containers allows you to remove applications from the image and dynamically provision them to end user desktops, reducing the complexity of migrating published applications to Server 2022. This avoids desktop and application silos, improving the scalability of your session hosts. By publishing applications to virtualize on launch, you ensure no resources are wasted when applications are not in use. Making this change now will help streamline future migrations, as you won’t need to reverse-engineer an existing image to create a new large image to migrate.


Enterprises have been reliant on Windows Server 2012 R2 for EUC workloads for various reasons. Microsoft has offered a lifeline in the form of free Extended Security Updates (ESUs) for those who choose to consume Azure services. Regardless, organizations must work toward a permanent solution for running their applications on modern operating systems. For EUC workloads, this may involve a migration from Windows Server operating systems to desktop operating systems. Packaging applications with containers can drastically streamline current and future migrations and streamline your migration from Server 2012 R2, regardless of the migration path you choose to go down.

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Numecent is an award-winning cloud technology provider headquartered in Irvine, California. The company’s technology portfolio, built upon 64 patents (and counting), simplifies the mobilization and management of Windows applications across modern desktop and multi-cloud environments. Enterprises around the world – including the largest Fortune 500 companies, cloud service providers, and MSPs – leverage these technologies to package and deploy thousands of applications to millions of end-users in a friction-free manner every day.

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