How to Perform an In-place Upgrade from Windows Server 2008 R2 to Windows Server 2019
If you are still running Windows Server 2008 R2, you might be wondering how to upgrade your server to a newer version of Windows Server. Microsoft has announced that Windows Server 2008 and Windows Server 2008 R2 are out of support on January 14th, 2020, which means you will no longer receive security updates and patches for these operating systems. However, you can still migrate your servers to Microsoft Azure and get three years of extended security support for free, or you can upgrade your servers to Windows Server 2019 and enjoy the latest features and improvements.
In this article, we will show you how to perform an in-place upgrade from Windows Server 2008 R2 to Windows Server 2019, which allows you to keep your settings, server roles, and data intact. However, before you start the upgrade process, you need to be aware of some prerequisites and limitations.
Prerequisites and Limitations
You can only perform an in-place upgrade from Windows Server 2008 R2 to Windows Server 2019 if you have Windows Server 2008 R2 Service Pack 1 installed. You can check your service pack level by running winver.exe from the Run dialog box.
You cannot perform an in-place upgrade from a 32-bit to a 64-bit architecture, or from one language to another. All releases of Windows Server since Windows Server 2008 R2 are 64-bit only.
You cannot perform an in-place upgrade if your server is an Active Directory domain controller. You need to demote the domain controller first, or perform a clean installation of Windows Server 2019.
You need to make sure that your hardware meets or exceeds the hardware requirements for Windows Server 2019. You can find the minimum hardware requirements on Microsoft Docs.
You need to have a valid product key and activation method for Windows Server 2019. The product key and activation method may depend on the distribution channel that you received Windows Server media from, such as Commercial Licensing, Retail, OEM, etc.
You need to have PowerShell 5.1 or later installed on your server. You can check your PowerShell version by running $PSVersionTable.PSVersion from a PowerShell prompt.
You need to have a location to store files away from your server, such as a USB flash drive or a network location. You will need this to backup your server data and collect diagnostic information in case the upgrade fails.
You need to review the compatibility of your server roles and applications with Windows Server 2019. Some server roles and applications may not be supported or may require additional steps before or after the upgrade. You can find more information on Microsoft Docs.
Once you have verified that your server meets all the prerequisites and limitations, you can follow these steps to perform an in-place upgrade from Windows Server 2008 R2 to Windows Server 2019:
Backup your server data and collect diagnostic information. We recommend that you backup your server operating system, apps, and virtual machines before starting the upgrade process. You also need to collect some information from your server for diagnostic and troubleshooting purposes in case the upgrade fails. To do this, open an elevated PowerShell prompt, make a note of your current directory, and run the following commands:
Then, using File Explorer, navigate to the directory you noted down, and copy the files to a USB flash drive or network location off of your server.
Shut down, quick migrate, or live migrate any virtual machines currently running on your server. You cannot have any virtual machines running during the in-place upgrade.
Insert the setup media for Windows Server 2019 and start the setup.exe file. If your server is connected to the internet, make sure you click on Go online to install updates now (recommended). This will download the latest updates to the aa16f39245