How to do a Windows Server in-place upgrade

Windows Server in-place upgrade to Windows Server 2019

 
Microsoft's standard support cycle ends on the 10 year anniversary of the release for most products. As such, we are reaching the end of extended support for Windows 2008 and Windows 2008 R2 servers in January 2020. All the system/server administrators still have 2 months to migrate their critical applications to a new Windows server.
 
This requires new hardware or virtual systems where applications and data can be migrated to. Users must verify with the vendor to check compatibility of applications with new OS versions, such as server 2012, server 2016 or 2019.
 
If the application is compatible with a newer version of the server operating system and you have a development environment available in your organization, you are able to do an in-place upgrade from Windows Server 2008 R2 to Windows 2012 R2, Server 2016 or even Server 2019. Follow the below steps to complete an in-place upgrade.
 
 
 
In my Lab, I have a wiki web server running on Windows 2008 R2. We will perform 2 step upgrades to upgrade windows server 2008 R2 to Windows Server 2019 in this article. It will cover all the steps including testing for an upgrade and a web server.
 
I am using a free wiki software called MediaWiki.
 
 

In-place upgrade to 2012

 
The first step will upgrade to Windows server 2012 R2 as an in-place upgrade. Attached is the ISO for Windows Server 2012 R2.
 
 
 
Select Run the setup.
 
 
Select Install Now. On the next page check for security and driver updates.
 
 
This will download the update package. The download will take 5 to 10 minutes, depending on your internet speed.
 
 
 
 
Select the version you need to install.
 
 
Select Upgrade, which allows you to install the new Windows with old files, settings, and application
 
 
This process will take 30 to 45 minutes depending on your system configuration.
 
 
Your system is ready with Windows 2012 R2. Login with the same user name password as your Server 2008 R2. Verify the server version.
 
 
Check the web application which we are using on Server 2008 R2.
 
 
 

Upgrade to Windows Server 2019

 
The next steps will walk through the upgrade from Windows Server 2012 R2 to Windows Server 2019. Attached is the ISO for Windows server 2019. On the next page, check for security and driver updates.
 
 
 
Select the version you need to install
 
 
To upgrade the current version, select Keep personal files and apps. This allows you to perform an in-place upgrade from Windows Server 2012 R2 or Windows server 2016 to Windows Server 2019.
 
 
 
 
 
This will check system and storage availability for the in-place upgrade.
 
 
Select Install to start the install.
 
 
 
Once the system is up after the upgrade, use the same user name password to login to the server.
 
 
Test the web application we are running on the server.
 
 
If all went well, we have successfully upgraded from Windows Server 2008 R2 to Windows Server 2019.
 
Note: Check with the application vendor for application compatibility with the Server version you plan on upgrading to.
 
I hope this article helps you upgrade your old Windows 2008 to the version you need to support a more secure infrastructure for your application.
 
Thank you for reading!