Whether you’re an MSP or an internal IT professional, you’re likely to use Windows Server. Windows Server is a group of operating systems specifically for server computers, with the latest update being Windows Server 2022, which was released in August 2021.

If you haven’t been keeping your IT calendar up to date, you may not have realized that the windows server 2012 r2 end of life deadline is fast approaching. As of October 10th, 2023, Windows will no longer provide patches, software updates, and security updates for these Windows server operating systems (Windows Server 2012 r2 and Windows Server 2012). This leaves you at a far greater risk of cyberattack, including malware injection, ransomware, or performance-related issues due to legacy systems or malicious actions like data or cryptocurrency mining.

Don’t panic! At Atera, we’ve got you covered. Here’s everything you need to know.

How should I go about upgrading Windows server?

First, know that the upgrade process itself can take a year. So it’s probably time to start thinking about it if you haven’t already. The latest upgradable version to use for 2012 or 2012 R2 is Windows Server 2019. Remember, you can upgrade Windows Server through two versions maximum. Below you can see your options, depending on which version you have.

Whichever option you choose, once we hit October 10, 2023, the official Windows Server 2012 end of life deadline, your systems will no longer receive security updates, even critical ones. As we said, this means that you will not be working compliantly, and you’re at far greater risk of vulnerabilities and gaps that lead to cyberattacks, including malware and ransomware.

On top of that, Windows Server 2019 and 2022 are more advanced operating systems. That means once you upgrade, your systems will run faster, and your business or your customer environments will have access to additional features, such as storage migration, system insights, and Azure network adapter.

We hope we have you convinced, and that you’re ready for an in-place upgrade! In-place is the simplest way to upgrade Windows Server edition, and it means you can keep your existing hardware and any current configurations, and simply move to the new version of Windows Server. A thorough how-to from Microsoft can be found here, including all prerequisites, how to gather essential diagnostic information before you begin, and how to check if your upgrade was successful.

If you just want to know how to get upgraded fast, here’s what you need to know, step by step.

Step one: Head to File Explorer and navigate to Windows Server Setup media. You’ll be prompted to open setup.exe. You may need to confirm you’re happy with the setup to make these changes necessary for the upgrade.

Step two: Setup will now begin the installation downloads. You can click “Next” to use the default settings, or you can change how the setup downloads updates if you would like to take more control over how updates are implemented moving forward.

Step three: You may need to enter your Product Key at this point, and you’ll then be prompted to choose which edition of Windows Server you would like to install. See the chart from Microsoft above to check your options. Psst: Make sure to read over the terms and conditions!

Step four: Here is where you ensure all existing configurations and data are kept. Select “keep personal files and apps” and then select “Next.” The ready-to-install screen will appear shortly, to which you can select “Install.”

Do I need to upgrade immediately? What about extended support?

In some cases, you might not be ready to upgrade to the latest Microsoft Server. Here’s how support for the product works.

Like all Windows Server editions, Windows Server 2012 and Windows Server 2012 R2 keep to Microsoft’s Fixed Lifecycle Policy. This means they offer 5 years of Mainstream Support, followed by 5 years of Extended Support. Here’s how they differ.

Mainstream support occurs during the first 5 years after a product release. It means all of the updates and product support available can be received, including security patches, service packs, incident support, and any changes to the product itself. For Windows Server 2012 R2, the Mainstream support period ended on October 9th, 2018.

Once this period ends, the product enters Extended support. Right now, Windows Server 2012 is in Extended support. That means security updates are received, but users can’t ask for any other updates, such as design changes or feature requests.

After Extended support is over, Microsoft announces End of Support, which is exactly what’s happening to Windows Server 2012 and 2012 R2 on the 10th of October 2023. There will be no more updates or support after this date.

I can’t be ready by that date! help!

For those who need to keep using Windows Server 2012 or 2012 R2 past the extended support date, there is a third option. You can opt into Microsoft’s premium plan, known as ESU, or Extended Security Update.

For up to three years after the Extended Support period ends, you can continue receiving updates and security and patch management support. ESU is available for free on Azure, and will incur an annual cost on-premises. The cost is worked out as a percentage of the license fee, 75% for year one, 100% for year 2, and 125% for year three.

This can get expensive fast, and really it is just putting off the inevitable, so it probably makes sense to get your ducks in a row for upgrading as early as possible, and only to use ESU while you are moving from legacy products, or getting your upgrade prerequisites ready. However, it’s definitely a lot smarter and more secure than continuing to use Windows Server 2012 or R2 once it’s reached the End of Support.

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