Microsoft Workloads on AWS

How to manually upgrade Microsoft Windows Server 2012 on AWS

This blog post is the first of a four-part series on how to upgrade Windows Server 2012 and 2012 R2. The focus of this series is to provide options to handle the upcoming end-of-support event in October. Part 1 overviews the end-of-support dilemma, plus how to perform an in-place, manual upgrade along with an insight into the End of Support Migration Program (EMP). Part 2 walks you through how to automate your upgrade using Amazon Systems Manager (SSM). Part 3 shows how to leverage modernization options, such as AWS App2Container, to handle an upgrade. Part 4 demonstrates how to upgrade Microsoft Windows Server 2012 using the AWS Application Migration Service.


Welcome to part one of a four-part blog post series on navigating the challenges of Windows Server end of support (EOS). This post begins with a discussion of the challenges surrounding EOS, and then walks you through manually upgrading Microsoft Windows Server 2012 R2 to Windows Server 2019 on AWS.


With Microsoft ending support for Windows Server 2012 on October 10, 2023, many IT stakeholders are unprepared for the event or unsure how to proceed. Not to worry, there are several options available for upgrading your software; however, understanding them and what will work for your team can be a challenge.

Microsoft, like other operating system (OS) and software vendors, regularly announces EOS dates for its products—usually 10 to 12 years after a release. Recent examples include Windows Server 2008 and 2008 R2, which reached EOS in January 2020, as well as databases like SQL Server 2012 and 2012 R2 in July 2022. This blog focuses on EOS for Windows Server 2012 and 2012 R2, both set to reach EOS on October 10, 2023.

Amazon Web Services (AWS) has many customers that use these two operating systems, and several of the methods and approaches that we will discuss will apply to EOS concerns in general. AWS can also help you if you have concerns surrounding the more difficult applications that need to be updated (see EMP section later in this blog post).

In this blog post, we will explore the technical concerns related to EOS and provide steps to manually upgrade Windows Server 2012 on AWS. The other posts in this series will provide additional options for upgrading. For a more detailed look at the Windows Server 2012 EOS issue from a business perspective, you can read this post: Know your AWS options for Microsoft Windows Server 2012 End of Support.

EOS challenges

The most obvious challenge is by continuing to use software beyond the EOS date, it no longer receives security updates, non-security updates, bug fixes, technical support, or online technical content updates. The only exception is if a customer has purchased extended security updates from the software provider. However, this type of purchase (either in the past or present) doesn’t address the larger concerns and just pushes problems into the future. It can force you to spend more money as well.

Other technical issues include:

  • Inability to upgrade the OS: Customers are unable to upgrade the OS due to application incompatibilities with newer versions of Windows Server.
  • Application incompatibility: Similar to the above point, some applications running on the EOS operating system can’t be upgraded.
  • Lack of knowledge or options: Many IT professionals may not know what tools are available to tackle the EOS problem.
  • Security and compliance concerns: Many regulated environments have requirements to keep applications and operating systems up to date. Older operating systems that cannot be patched remain vulnerable to malware, ransomware attacks, and security breaches.
  • Lack of staffing or funding to handle the EOS issues: Often, the EOS date is not IT’s primary concern and is pushed down the priority list.
  • Some solutions are too costly: Some extended support products, solutions, and offers can look good on paper to an IT department, but many times the offers are costly and are not adopted in a timely manner.
  • Lack of new features and innovation: Older operating systems don’t have the new features and capabilities we expect from current software.

Now that we have established some of the key EOS technical challenges, let’s look at how AWS can help you address them. Doing nothing isn’t an option in today’s business environment.

The AWS technical solution to EOS

AWS and our partners are focused on helping you migrate, upgrade, and modernize your Windows Servers workloads with dedicated programs, tools, and technical assistance. As you are assessing your environment and reviewing your Microsoft licensing options, you can rely on AWS to help you throughout your journey.

In the following section, we walk through the manual upgrade process for Windows Server 2012 R2. Please note that this approach, and the methods mentioned in the related blog post series, can also apply to older EOS operating systems, such as Windows 2008 R2. An overview of supported Windows Server upgrades can be found here.

Before you begin, it’s important to test (instructions not included in this post or series) and make sure the applications running on the upgraded OS are fully functional.


We previously published a blog post titled: How can I upgrade my Amazon EC2 Windows Server instance OS to a newer version? In that post, we shared guidance on how to complete a server migration for an Amazon Elastic Compute Cloud (Amazon EC2) instance. That post will provide a helpful reference to accompany this upgrade.

Before starting the upgrade, create an Amazon Machine Image (AMI) or create a snapshot of the Amazon Elastic Block Storage (EBS) volumes. This step provides an additional layer of protection if there’s an issue during the upgrade process. We always recommend that you have a backup prior to testing any of the options.

In our EC2 User Guide for Windows, we recommend you perform an in-place upgrade by using our public installation media. Please note that if you are planning to upgrade a BYOL version of Windows Server, you will need to create your own installation media. This video demonstrates how you can upgrade a t2.large EC2 instance running Windows Server 2012 R2. Depending on when the instance was deployed, there are additional steps that you need to take before starting, including:

  1. From the AWS Management Console, collect the instance ID of the Windows Server that you are going to be upgrading. You’ll need this later.
  2. Ensure that you have at least 10 GB of free disk space.
  3. Make sure you have the latest paravirtual (PV) drivers on the instance, by comparing to the list in our user guide.
  4. Older generation systems might have the EC2ConfigService installed. This will need to be removed and replaced with our new EC2Launch service.
  5. Ensure that the Amazon Systems Manager (SSM) agent is installed on the instance as well. This will allow you to run any additional automation and manage the instance going forward.
  6. Go to your Amazon EC2 console, as shown in figure 1.
  7. Under the Elastic Block Store dropdown, select Snapshots.

    The Amazon EC2 console highlighting Snapshots.

    Figure 1. Amazon EC2 console displaying a list of “Snapshots”

  8. In Search (as shown in Figure 2), include the following filters: Owner Alias = “amazon” and Description: “Windows 2019 English Installation Media.”

    The Amazon EC2 console entering Windows 2019 English Installation Media filter

    Figure 2. Amazon EC2 console entering Windows 2019 English Installation Media filter

  9. As shown in Figure 3, select and check the snapshot. Then click on Actions and select the Create volume from snapshot from the dropdown.

    Amazon EC2 Console showing snapshot list and action “create volume from snapshot”

    Figure 3. Amazon EC2 console showing snapshot list and action “create volume from snapshot”

  10. When you create the volume (as shown in Figure 4), make sure you select the correct Availability Zone that your instance is located, scroll down to the end, and then select Create volume.Amazon EC2 console showing volume settings menu, how to check instance is in correct availability zone and action “create volume”Figure 4. The volume settings menu, how to check instance is in correct availability zone and action “create volume”
  11. Once you create the volume, select it to view details and attach it to the instance (as shown in figure 5).

    Amazon EC2 console showing a successful volume creation

    Figure 5. A successful volume creation

  12. To attach the volume, select Actions. Then select Attach volume from the dropdown (as shown in Figure 6).

    Amazon EC2 console specific volume details screen showing action and attachment of volume

    Figure 6. The Attach Volume Details screen

  13. In the Attach volume window, select the instance that you want to upgrade from the list. Then select Attach volume (as shown in Figure 7).

    Amazon EC2 console specific volume details screen showing action and attachment of volume

    Figure 7. Attach Volume basic details screen

  14. Use RDP or Amazon Fleet Manager to connect to the instance. Then attach the volume to the Windows 2012R2 machine using Disk Management. You can use the GUI or run diskmgmt.msc from a PowerShell console.
  15. Right-click on the volume and set it to Online (as shown in Figure 8).

    Amazon EC2 console Disk Management screen showing how to set the volume “Online”

    Figure 8. Use Disk Management to set the volume to “Online”

  16. This will mount the drive, which is now attached to the system as the d:\ drive (as shown in Figure 9).

    Amazon EC2 console shows how volume D: is now attached to the system

    Figure 9. Volume D: is now attached to the system

It’s time to launch the upgrade: Open a PowerShell console and change the directory to the drive that you have just mounted, and submit the following command: ./setup.exe /auto upgrade.

If we’ve done everything correctly, you should see a Windows Server 2019 Setup install window. Select Windows Server 2019 Datacenter edition (as shown in Figure 10).

Windows Powershell Image Selection showing how to select Windows Server 2019 Datacenter (Desktop Experience)

Figure 10. Windows Powershell image. Select Windows Server 2019 Datacenter (Desktop Experience)

Continue the upgrade by following the on-screen prompts until completion. The system will restart a couple of times during the upgrade process.

Once the OS upgrade is complete, you can validate the functionality of your applications before you put the system back in production.

This approach shows you exactly how to proceed with the upgrade. No cleanup steps required!

AWS can help migrate difficult legacy Windows Server applications to the latest, supported versions of Windows Server on AWS, using the End-of-Support Migration Program (EMP) for Windows Server. EMP includes tooling to migrate your legacy applications from Windows Server 2003, 2008, and 2012 to newer, supported versions on AWS. You can use the EMP tool freely as a self-service option or with the help of AWS Partners or AWS Professional Services.

In this blog post, we discussed the challenges surrounding the Windows Server EOS from a technical perspective and why you should take action to upgrade. In addition, we walked through the manual upgrade option for Windows Server 2012 and 2012 R2.

Please keep in mind that this four-part blog series has discussed and presented many options for dealing with EOS and how AWS can help you address these issues with the use of technology, tooling, and experts.

If you would like help, please reach out so we can learn about your specific EOS situation and help you upgrade on AWS.

AWS can help you assess how your company can get the most out of cloud. Join the millions of AWS customers that trust us to migrate and modernize their most important applications in the cloud. To learn more on modernizing Windows Server or SQL Server, visit Windows on AWSContact us to start your migration journey today.

Mike Adams

Mike Adams

Mike Adams is a worldwide go-to-market specialist with AWS. His focus is migrating Microsoft workloads to AWS and showing customers how they can achieve operational and cost efficiencies. Prior to AWS, Mike held product marketing roles at Ivanti, VMware, Symantec, and VERITAS Software. Mike started his career as an industry analyst at the Giga Information Group (now part of Forrester Research).

Gianpaolo Albanese

Gianpaolo Albanese

GianPaolo Albanese is a Microsoft Specialist Solutions Architect with Amazon Web Services based in the New York area. GP is focused on helping customers with their Windows architectures, migrations and optimization to the AWS cloud. GP has been an IT professional with over three decades of experience in the FinTech industry, specialized in the management of large-scale infrastructures, migrations and modernization activities. In the past two years, GP has focused his energy to help customers address End-of-Support challenges.