Updated February 3, 2026 – Originally published July 27, 2023
Windows 2012 R2 has been an IT mainstay for over a decade, serving as the go-to operating system for businesses seeking the benefits of a modern Windows platform without the tablet-like interface of its predecessor, Windows 2012. If you’re reading this, chances are you have or have had servers running Windows Server 2012 R2. However, the time has come to develop a plan to update your systems or migrate to the cloud. Why? Because in October of 2023, Windows 2012 R2 reached end-of-life (EOL) status. Extended Support Upgrades were available, but those are coming to an end soon too. By October 2026, Windows Server 2012 will be unsupported. If you’re on ESUs, you need to plan to update your systems in 2026.
In this blog, we’ll explore the available options for updating your systems to ensure you remain protected and productive.
What happens when Windows Server 2012 R2 goes “end of life (EOL)”?
In the technical world, “end of life” or EOL basically means being left without support. This implies that regular security updates, bug fixes, and patches will no longer be provided. Microsoft has shifted its focus towards its newer operating systems, so troubleshooting issues for older systems are no longer their priority. As a result, you won’t have access to technical support from Microsoft for Windows Server 2012, even if you’re willing to pay for it. This can potentially lead to significant costs for your business if unforeseen problems arise.
The risks of running an unsupported system
Having systems at EOL status can create issues – security and otherwise. Since these are no longer regularly patched, it creates an opportunity for vulnerabilities to be exploited. Additionally, most MSPs won’t work with systems that aren’t supported.
An unsupported system is an easier target for threats. While there’s no way to ensure complete security in your IT environment, keeping systems up to date and leveraging current, supported versions is a great way to make things more difficult for cybercriminals.
What about Windows Server 2016 & 2019?
Microsoft leverages an N+1 support model, meaning it only focuses its efforts on the most current operation systems and the system that came before that. At this time, that is Windows Server 2022 and later. Notice that Windows Server 2016 and Windows Server 2019 are not on this list, either. Support for these is currently in the extended support phase, meaning all Microsoft Support comes with a fee.
If your infrastructure is currently on Server 2016 or 2019, it’s considered “Extended Support” and it’s also time to start planning that roadmap to a newer OS. Even if you did purchase the Extended Support (ESU) for Server 2016, it will expire in January 2027. To avoid any gaps in support, plan to move off Windows Server 2016 in 2026. For 2019, mainstream support has ended but with ESU you’ll have until the end of 2029. Either way, it’s a great time to start planning to upgrade or move your infrastructure to the cloud.
Options for upgrading Windows 2012 R2 Server
There are a few different options for upgrading your existing Windows 2012 R2 instances. Discuss which one to choose with your IT partner.
- Upgrade your servers. Traditionally the approach for most businesses when facing an EOL situation is to replace or upgrade that equipment. It is no different for your Windows Server OS, however, it may be more complex. In-place upgrades are an option, but not recommended as best practice by Microsoft. The most well-rounded solution is to migrate your workloads to new servers running supported operating systems. Windows Server 2022 and SQL Server 2022 are both available options.
- Migrate to Azure. For most organizations, moving to the cloud is a great choice. It’s scalable, flexible, and easy to keep current. A properly managed cloud environment can help you find opportunities for cost optimization and resource savings. When implemented correctly, Azure can be more secure too. Azure’s capabilities include moving to dedicated instances for SQL, replacing Remote Desktop Services with Azure Virtual Desktops, Azure Files, and many more.
- Purchase Extended Security Updates. Microsoft offers the option to purchase Extended Security Updates (ESUs) for a period of three years, although it isn’t recommended. ESUs can be helpful during the transition period but aren’t a long-term solution. While they help with the security piece, there’s still a gap when it comes to support. Extended Security Updates can take you through until October of 2026 and the pricing of these increases each year. The option to purchase ESUs is only available to customers with Software Assurance (SA) licensing and an Enterprise Agreement. Typically this rules out clients in the SMB space, who due to size would not have an Enterprise Agreement.
ADNET’s recommendation for the end of Windows Server 2012 R2
Our overall recommendation is to get your systems up to date, but the decision on how to do that should be made on a case-by-case basis. First, ADNET recommends evaluating the current servers and the roles they are performing. Analyzing what’s currently running on your servers can guide you toward the best option for your organization. In many instances, scaling your server instances more effectively in the cloud with Microsoft Azure is an ideal solution.
Depending on what you’re running on your servers, moving to a currently supported system may require a more complex configuration or a complete migration. That’s why it’s crucial to create a migration plan as soon as possible. Waiting until the last minute could lead to periods of vulnerability and potential loss of productivity if any issues arise.
From a budget standpoint, planning is key to efficiency and cost-savings. Server upgrades should be considered as part of your complete IT strategy, rather than individual projects. Does it make sense to move to the cloud now if that’s on your roadmap in two years? These are the types of questions that are easier to answer when you look at your whole IT strategy, rather than piece by piece.
Talk to a trusted IT partner like ADNET if you have questions on what recommendation is right for your business. If you have other systems, such as VMware or your Hyper-V host, that are at or nearing their End of Life, factor those into your decisions regarding your servers.
Need to upgrade your Windows Servers?
With so many options, it’s always helpful to discuss your IT strategy and business goals with your trusted IT partner before making any decisions that could have short and long-term impacts.
Embarking on the prospect of migrating your IT infrastructure to the cloud can be a daunting task on your own. There’s no right answer, only what’s right for your business. If you need help getting your servers and systems current reach out to us – we’re happy to talk through which option makes the most sense for your organization. Our team can help with everything from migration and implementation to support. Reach out to us to learn more.
