Upgrading Windows Server 2012 R2 to Windows Server 2019

Question

Dear Microsoft Experts

I'm seeking your support in upgrading Windows Server 2012 R2 to Windows Server 2019

I have two Windows Server 2012 R2 with keep the configurations and data as current

Server 1

• Primary Domain Controller role
• DNS Server role
• DHCP Server role

Server 2

• Additional Domain Controller

The servers are virtual machines and running normally.

The steps I plan to take for the update are as follows:

1. Mount file ISO Windows Server 2019 on Server 1 and proceed with the upgrade with the keep file option
2. After done with Server 1, follow the same steps as above with Server 2

I would like to ask if this is okay to do and if anyone here has a similar scenario and has done it before, please share your experience with me.

Thank you in advance

Answer 1

Hello,

It is okay to follow what you say.

Before doing in-place upgrade,

• Make sure you have valid product keys and activation method.
• Have a location to store files away from your computer, such as a USB flash drive or network location.
• Review Upgrade and migrate roles and features in Windows Server.
• Review Microsoft server applications compatibility.
• Review any third-party application vendor support requirements.
• Make sure your computer:
  • Meets or exceeds the hardware requirements for Windows Server.
  • Isn't running in Azure.
• Perform a full backup of your computer. This includes the operating system, apps, data, and any virtual machines (VMs) running on the server. You can use Windows Server Backup or a third-party backup solution.

More details you can refer to this official link:

https://learn.microsoft.com/en-us/windows-server/get-started/perform-in-place-upgrade

Best Regards,

Hania Lian

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Answer 2

Hi Hania

"Isn't running in Azure" What does it mean?

My organization is running Azure Hybrid AD Joined, but the server on which the Azure AD connectivity tool is installed is a different server (installed Windows Server 2019)

Answer 3

Hello,

It is possible but not recommended to perform an in-place upgrade of a Windows server in Azure, especially if upgrading from an older version such as Windows Server 2012 R2 to Windows Server 2019. This is because the design philosophy and operational strategy of the Azure platform are different from traditional on-premises data environments, and performing in-place upgrades to virtual machines directly in Azure can introduce a series of problems and risks.

Best Regards,

Hania Lian

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