As you know the Windows Server 2008 and Windows Server 2008 R2 are out of support on January 14th, 2020. Customer will need to upgrade their Windows Server 2008 and Windows Server 2008 R2 to a newer version of Windows Server or migrate these servers to Microsoft Azure and get three years of extended security support for free, which will give you more time to upgrade your servers, redeploy your apps or rearchitect your applications. If you want to have more information about how to migrate your servers to Azure, check out the Azure migration center. There are many ways you can migrate your server applications to a newer version of Windows Server. This blog post covers how you in-place upgrade Windows Server 2008 R2 to Windows Server 2019. You can find more information about Windows Server 2019 installations and upgrades on Microsoft Docs.
To help you with Windows Server upgrades, the Windows Server team created Windows Server Upgrade Center, which gives you step-by-step guidance for modernizing your datacenter.
You can directly do an in-place upgrade to Windows Server 2019 from Windows Server 2016 and Windows Server 2012 R2. This means, to upgrade from Windows Server 2008 R2 to Windows Server 2019, you will have two consecutive upgrade processes.
Not all server roles and applications are supported to be migrated in older versions of Windows Server. Read the specific documentation for your operating system scenario, for example upgrading roles to Windows Server 2016. As an alternative, you can also redeploy the applications on a fresh installation of Windows Server 2019.
Before you start in-place upgrade your servers, make sure you plan your upgrade and make sure you have all the information, to avoid surprises at the end of the migration. The Windows Server Upgrade Center helps you with a checklist which includes, for example, the following:
Before you start the upgrade process you should also collect the following system information. You can use the following to commands. Please save the output on another location.
mkdir C:\info systeminfo > C:\info\systeminfo.txt ipconfig /all > C:\info\ipconfig.txt
Please copy and save the systeminfo.txt and ipconfig.txt file on another system.
I know I have mentioned it before, make sure you have a backup you can restore of the server you are performing the in-place upgrade. Also, make sure that you are aware that the following upgrade processes cause downtime.
Insert the setup media for Windows Server 2012 R2 and start the setup.exe.
Click Install now.
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 installer.
Enter the Windows Server License Key for Windows Server 2012 R2 if needed. If you are not asked for the license key, you can skip that step.
Select the right Windows Server edition you want to install. Also make sure you select Server with a GUI or Server Core Installation, depending on your needs.
Read and accept the license terms. Select I accept the license terms.
For an in-place upgrade select Upgrade: Install Windows and keep files, settings, and applications.
The setup will check the application compatibility and create a compatibility report.
Next, press Confirm to start upgrading Windows.
The setup will complete and automatically reboot. When the upgrade is done, you will see the Windows Server 2012 R2 logon screen.
After the upgrade to Windows Server 2012, log in and check if the server has been successfully upgraded. Make sure you test if the applications are running like expected and if users can access the application. Make sure that the IP and firewall configuration of your server still allows clients to access your system.
You can run the following command to see that you successfully upgraded to Windows Server 2012:
systeminfo
If there has been an issue with the upgrade, make a copy and zip the %SystemRoot%\Panther (usually C:\Windows\Panther) directory and contact support.
If everything works as expected, you can install the latest Windows Server 2012 R2 updates, and make sure your server is fully patched. Before you move to the Windows Server 2012 R2 to Windows Server 2019 upgrade, I also recommend that you create a backup of the server, in that case, you don’t lose the work you did from 2008 R2 to 2012 R2.
Insert the setup media for Windows Server 2019 and start the setup.exe.
Click Install now.
If your server is connected to the internet, make sure you click Download and install updates, drivers and optional features (recommended). This will download the latest updates to the installer.
Enter the Windows Server License Key for Windows Server 2019 if needed. If you are not asked for the license key, you can skip that step.
Select the right Windows Server edition you want to install. Also make sure you select Windows Server 2019 Datacenter (Desktop Experience) or Windows Server 2019 Datacenter (Core), depending on your needs.
Read and accept the license terms. Select I accept the license terms.
For an in-place upgrade, select Keep personal files and app and click Next.
The setup will check the application compatibility and create a compatibility report.
Next, press Install to start upgrading Windows.
The setup will complete and automatically reboot. When the upgrade is done, you will see the Windows Server 2019 logon screen.
After the upgrade to Windows Server 2019, log in and check if the server has been successfully upgraded. Make sure you test if the applications are running like expected and if users can access the application. Make sure that the IP and firewall configuration of your server still allows clients to access your system.
You can run the following command to see that you successfully upgraded to Windows Server 2019:
systeminfo
If there has been an issue with the upgrade, make a copy and zip the %SystemRoot%\Panther (usually C:\Windows\Panther) directory and contact support.
If everything works as expected, you can install the latest Windows Server 2019 updates, and make sure your server is fully patched. I also recommend that you create a backup of the server; in that case, you don’t lose the work you did.
I also highly recommend that you have a look at Windows Containers to modernize your applications. Check out our full video here on Microsoft Channel 9:
There are many ways you can upgrade or migrate your applications, in-place upgrade is just one of them, and might not always fit. However, in some scenarios, it is the easiest way to get to a newer version of Windows Server. I hope this gives you an overview about how you can do in-place upgrades from Windows Server 2008 R2 to Windows Server 2019. If you have any questions or tips for the upgrades, leave a comment below.
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