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Microsoft

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.

 

Upgrade path

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 three consecutive upgrade processes.

 

  • First, you upgrade Windows Server 2008 R2 to Windows Server 2012
  • Secondly, you will upgrade Windows Server 2012 to Windows Server 2016
  • Finally step, you upgrade Windows Server 2016 to Windows Server 2019

Windows-Server-Upgrade-Path.jpg

 

 

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.

 

Planning the Upgrade

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:

 

  • What software and roles are installed on the server and are they supported and working with newer versions of Windows Server. I recommend doing a software inventory and check if the applications and roles are supported.
  • Have some tests ready to check if the application still works after the upgrade. It is a good thing to run through these tests before the upgrade as well, so you can confirm everything is working correctly.
  • If it is a physical server, do you have drivers and firmware updates for the new Windows Server version available?
  • Think about backup software and antivirus, you might need to uninstall these during the update process and reinstall it after the upgrade is done.
  • Make sure your server is up-to-date and fully patched before doing an in-place upgrade.
  • Planning the timeframe for the upgrade. In-place upgrades take some time, make sure you have a long enough maintenance window planned. Also make sure you communicate the maintenance window, so users know that the application or service is not available.
  • Make sure you have a backup of the server before you start the upgrade process, and make sure you can also restore from that specific backup.
  • If possible, test the upgrade process with a non-production server.
  • Make sure you have enough disk space for the upgrade.
  • Gather your system information before the upgrade.

 

Collect system information

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.

 

Windows Server 2008 R2 Collect System Info.jpgWindows Server Systeminfo

 

Before proceeding with the In-place Upgrade

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.

 

Upgrade Windows Server 2008 R2 to Windows Server 2012

Insert the setup media for Windows Server 2012 and start the setup.exe.

Click Install now.

 

Windows Server 2012 Installation Setup.jpgWindows Server 2012 Installation Setup

 

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.

 

Windows Server 2012 Setup Installer Update.jpgWindows Server 2012 Setup Installer Update

 

Enter the Windows Server License Key for Windows Server 2012 if needed. If you are not asked for the license key, you can skip that step.

 

Windows Server 2012 License Key.jpgWindows Server 2012 License Key

 

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.

 

Windows Server 2012 Operating System.jpgWindows Server 2012 Operating System

 

Read and accept the license terms. Select I accept the license terms.

 

Windows Server 2012 License terms.jpgWindows Server 2012 License terms

 

For an in-place upgrade select Upgrade: Install Windows and keep files, settings, and applications.

 

Windows Server 2012 Upgrade.jpgWindows Server 2012 Upgrade

 

The setup will check the application compatibility and create a compatibility report.

 

Windows Server 2012 Compatibility report.jpgWindows Server 2012 Compatibility report

 

Next, press Confirm to start upgrading Windows.

 

Windows Server 2012 Upgrading Windows Server.jpgWindows Server 2012 Upgrading Windows Server

 

The setup will complete and automatically reboot. When the upgrade is done, you will see the Windows Server 2012 logon screen.

 

Windows Server 2019 Logon Screen.jpgWindows Server 2019 Logon Screen

 

Post Upgrade to Windows Server 2012

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

 

Windows Server 2012 Systeminfo.jpgWindows 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 updates, and make sure your server is fully patched. Before you move to the Windows Server 2012 to Windows Server 2016 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.

 

Upgrade Windows Server 2012 to Windows Server 2016

Insert the setup media for Windows Server 2016 and start the setup.exe.

Click Install now.

If your server is connected to the internet, make sure you click Download and install updates (recommended). This will download the latest updates to the installer.

 

Windows Server 2016 Update Setup.jpgWindows Server 2016 Update Setup

 

Enter the Windows Server License Key for Windows Server 2016 if needed. If you are not asked for the license key, you can skip that step.

 

Windows Server 2016 Product Key.jpgWindows Server 2016 Product Key

 

Select the right Windows Server edition you want to install. Also make sure you select Windows Server 2016 Datacenter (Desktop Experience) or Windows Server 2016 Datacenter (Core), depending on your needs.

 

 

Windows Server 2016 Select Image Edition.jpgWindows Server 2016 Select Image Edition

Read and accept the license terms. Select I accept the license terms.

 

Windows Server 2016 license terms.jpgWindows Server 2016 license terms

 

For an in-place upgrade, select Keep personal files and app and click Next.

 

Windows Server 2016 Keep personal files in-place uprgade.jpgWindows Server 2016 Keep personal files in-place upgrade

 

In the Windows Server 2016 setup.exe, one page says that upgrade is not recommended, in order to encourage customers to prefer clean installation. Note: this page has been removed from Windows Server 2019 setup.exe.

To continue with the in-place upgrade press Confirm.

 

Windows Server 2016 Comfirm in-place upgrade.jpgWindows Server 2016 Confirm in-place upgrade

 

The setup will check the application compatibility and create a compatibility report.

Next, press Install to start upgrading Windows.

 

Windows Server 2016 in-place upgrade.jpgWindows Server 2016 in-place upgrade

 

The setup will complete and automatically reboot. When the upgrade is done, you will see the Windows Server 2016 logon screen.

 

Windows Server 2016 Logonscreen.jpgWindows Server 2016 Logon screen

 

Post Upgrade to Windows Server 2016

After the upgrade to Windows Server 2016, 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 2016:

 

 

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 2016 updates, and make sure your server is fully patched. Before you move to the Windows Server 2016 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 2012 to 2016.

 

Upgrade Windows Server 2016 to Windows Server 2019

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.

 

Windows Server 2019 Update Installer.jpgWindows Server 2019 Update Installer

 

Enter the Windows Server License Key for Windows Server 2016 if needed. If you are not asked for the license key, you can skip that step.

 

Windows Server 2019 Product Key.jpgWindows Server 2019 Product Key

 

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.

 

Windows Server 2019 select image edition.jpgWindows Server 2019 select image edition

 

Read and accept the license terms. Select I accept the license terms.

 

Windows Server 2019 license terms.jpgWindows Server 2019 license terms

 

For an in-place upgrade, select Keep personal files and app and click Next.

 

Windows Server 2019 in-place upgrade.jpgWindows Server 2019 in-place upgrade

 

The setup will check the application compatibility and create a compatibility report.

Next, press Install to start upgrading Windows.

 

Windows Server 2019 in-place upgrade install.jpgWindows Server 2019 in-place upgrade install

 

The setup will complete and automatically reboot. When the upgrade is done, you will see the Windows Server 2019 logon screen.

 

Windows Server 2019 Logon Screen 2.jpgWindows Server 2019 Logon Screen 2

 

Post Upgrade to Windows Server 2019

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.

 

Conclusion

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.

5 Comments
Occasional Visitor

Thanks for that.

Wich Server Rules are not able to make in In Place Upgrade? I know that the RDS Role is a big Problem.

Senior Member

In-Place Upgrade from Server 2008 R2 to Server 2012 R2 is possible, there's even a blog post on Technet about it (https://blogs.technet.microsoft.com/chrisavis/2013/10/01/performing-an-in-place-upgrade-of-server-20...).

 

Why is this (supposedly) not supported? This would cut the upgrade path from 3 to 2 upgrades (2008 R2 -> 2012 R2 -> 2019). Because as far as I see it, every upgrade is a place things can go wrong. The majority of our servers run third party software and do not rely on Windows Server roles.

Microsoft

Hi @saschaf84 

You can find information about the different roles for 2012-2016 here: https://docs.microsoft.com/en-us/windows-server/get-started/server-role-upgradeability-table

 

I hope this answers your question.

Frequent Visitor

Good article but no mention of the requirement to reinstall .NET4.5.2, the possibility of losing your static IP, or the Net.Tcp Port Sharing Service that gets set to Disabled preventing the other Net.* services from starting.  Also, a big gotcha is if you have WSUS role installed, you have to uninstall the role (but you don't have to delete the DB).  

Occasional Visitor
Thank you for sharing, why not upgrade to Windows 2008 R2 directly instead Windows 2008