Finish – Virtualization Review

Upgrading Windows Server 2012 EC2 Instances, Part 3: Completion

Windows Server 2012 is reaching its expected end of life in 2023. As such, organizations should start planning to upgrade to a supported Windows Server operating system now.

EC2 instances that are running Windows Server 2012 and 2012 R2 will continue to function after the end of life date, but Microsoft will no longer provide security fixes. Thus, it is in an organization’s best interest to go ahead and update their EC2 instances to a newer operating system.

In Part 1 of this blogging series, I discussed some planning issues related to the upgrade process, and in Part 2 of the series, I started the practical part. The last thing we did in part 2 was create a virtual disk that contains the Windows Server installation files and then attach that virtual disk to the EC2 instance being upgraded. For the purposes of this blogging series, I’ll be switching to Windows Server 2019, but the walkthrough I’m about to show you works the same for all versions of Windows Server.

Now that you have attached the volume containing the installation files to the instance, you need to make this volume accessible to the existing Windows operating system. From the virtual machine, enter the diskmgmt.msc at the Windows run prompt. This will cause Windows to open the Disk Management Console. You will need to use this console to bring the drive online.

In some cases, you will be lucky and the new disc will automatically upload. However, if the Disk Management Console does not indicate that the disk is online, you will need to right click on the disk and choose the Online option from the context menu. By the way, be careful not to accidentally choose Initialize option as it will lead to data loss.

Figure 1: The drive is now online.
[Click on image for larger view.] Figure 1: The disc is now online.

Once the new disk is uploaded, you will be able to access the Windows installation files stored on the disk. This means that you can now proceed to upgrade the operating system. As you can see in the figure below, the disc you uploaded contains the Windows installation files. You can use these files to perform an in-place upgrade of Windows.

Figure 2: The newly attached volume contains the Windows installation files.
[Click on image for larger view.] Figure 2: The newly attached volume contains the Windows installation files.

To initiate the upgrade, open an Administrative PowerShell window and enter the following commands:

./Setup.exe /auto upgrade

If you find that these commands do not work, check the Disk Management console to see if the new volume has been mapped to a drive letter other than D :, and then perform the substitution. As you can see in the following figure, this starts the Windows installation process.

Figure 3: We have launched the Windows installer.
[Click on image for larger view.] Figure 3: We have started the Windows installation.

At this point, there are a few things you need to do to complete the upgrade process. First, you are going to need to choose the operating system you want to install, as shown in Figure 4. You will generally want to match the edition currently in place since you are upgrading in place.

Figure 4: Choose the operating system you want to install.
[Click on image for larger view.] Figure 4: Choose the operating system you want to install.

The other thing you might need to do is specify whether you want to upgrade or a clean install of Windows Server. AWS will not always display this prompt (due to the upgrade switch used with setup.exe), but if it does, be sure to choose the upgrade option. Otherwise, the installer will overwrite your apps and settings.

The time required to complete the upgrade can vary widely. Eventually, the upgrade process should complete. You can see the newly upgraded Windows operating system in the following figure.

Figure 5: The upgrade process is complete.
[Click on image for larger view.] Figure 5: The upgrade process is complete.

About the Author

Brien Posey is 20 times Microsoft MVP with decades of IT experience. As a freelance writer, Posey has written thousands of articles and contributed to several dozen books on a wide variety of computer topics. Prior to becoming independent, Posey was CIO for a national chain of hospitals and healthcare facilities. He has also served as a network administrator for some of the largest insurance companies in the country and for the Department of Defense at Fort Knox. In addition to his continued work in computer science, Posey has spent the last few years actively training as a commercial scientist-astronaut candidate to fly on a cloud study mission. Polar mesospheres from space. You can take his space flight training on his Website.

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