How to In-Place Upgrade Windows Server 2008 R2 to Windows Server 2019
Published Jul 23 2019 12:05 AM 401K Views
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 two consecutive upgrade processes.

 

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

 

Windows Server Upgrade Paths DiagramWindows Server Upgrade Paths Diagram

 

 

 

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 SysteminfoWindows 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 R2

Insert the setup media for Windows Server 2012 R2 and start the setup.exe.

Click Install now.

 

Windows Server 2012 R2 Installation Setup.jpg

 

 

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 R2 Update Setup.jpg

 

 

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.

 

Windows Server 2012 R2 Key.jpg

 

 

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 R2 Operating System.jpg

 

 

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

 

Windows Server 2012 R2 License terms.jpg

 

 

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

 

Windows Server 2012 R2 Upgrade.jpg

 

 

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

 

Windows Server 2012 R2 Compatibility report.jpg

 

 

Next, press Confirm to start upgrading Windows.

 

Windows Server 2012 R2 Upgrading.jpg

 

 

The setup will complete and automatically reboot. When the upgrade is done, you will see the Windows Server 2012 R2 logon screen.

 

Windows Server 2012 R2 Logon Screen.jpg

 

 

Post Upgrade to Windows Server 2012 R2

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 SysteminfoWindows 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.

 

Upgrade Windows Server 2012 R2 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 InstallerWindows Server 2019 Update 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.

 

Windows Server 2019 Product KeyWindows 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 editionWindows Server 2019 select image edition

 

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

 

Windows Server 2019 license termsWindows Server 2019 license terms

 

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

 

Windows Server 2019 in-place upgradeWindows 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 installWindows 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 2Windows 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.

 

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:

 

 

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.

25 Comments
Copper Contributor

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.

Brass Contributor

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.

Copper Contributor

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).  

Copper Contributor
Thank you for sharing, why not upgrade to Windows 2008 R2 directly instead Windows 2008
Copper Contributor
When performing this multi level in place upgrade, do you have to buy retail versions of 2012, 2016, and 2019 server software? Can you use free evaluation versions of 2012 and 2016 since they are only temporary installs, and then buy the retail version of 2019? Most of my customers have small business servers ( less than 10 clients ) not acting as a DC that mostly provide just file sharing, and host data for network programs. It would be a major expense to buy 3 versions of MS server software for each install.
Copper Contributor

I'm also very interested to know the answer to Ruecom's question. 
Can I upgrade from 2008 R2-Standard to 2012 R2-Evaluation to 2019-Standard?? 
If someone can provide a response asap I would greatly appreciate it. I have a scheduled server upgrade in 2 weeks. 

Copper Contributor

Thanks for that.

but can i have a question?

my company have a plan for upgrade from server 2008 to 2019,can you show me when I upgrade that,all of Files data,policies or scripts maybe lost of them or not,and how many percentages file will be upgrade successful and not be lost ( 80 or 90%) because i"m worries about the lost data,and maybe i Will backup all of them before upgrade.

 

Please help me how to do it

P/s: i'm so sorry if my English not good and write not well

Thanks & have a nice day

 

Microsoft

@ngotung You should definitely do a backup before upgrading. Usually an in-place upgrade should not remove any files. However, it is always highly recommended to do a backup and have a fall back plan.

Copper Contributor

@thomasmaurer Thanks for your support,it's very helpful to me

Copper Contributor

Do you need to buy a license for both 2016 and 2019? I know it says to enter the license key "if needed" but is it needed or not? 

Copper Contributor

I needed to upgrade my forest schema between 2008R2 and 2012R2. Not sure how unusual it is, but here is the procedure to do that : https://docs.microsoft.com/en-us/previous-versions/windows/it-pro/windows-server-2008-R2-and-2008/cc...

That document is not up to date, so you need to do adprep /domainprep as well after the command documented there - see https://serverfault.com/questions/424899/upgrade-to-windows-server-2012-from-windows-server-2008-r2 

 

The same needs to be done when upgrading from 2012R2 to 2019.

Microsoft

@TaterSalad333 A lot of licenses come with downgrade rights, for example, if you have a Windows Server 2019 license with downgrade rights, you can also install Windows Server 2016. So check if the type of license you bought covers that.

Copper Contributor

I'm facing a really weird problem executing a in-place upgrade of a server 2008 r2 to 2008 r2, already executed the process 2 times, and without any kind of error or alert it just remove the IIS role that is installed on the server.

 

I'm trying this in-place upgrade to solve windows updates errors... i have lots of old packages on missing state, and it just impossible to update the server.

 

Did someone found this IIS role missing on in-place upgrade?

Brass Contributor

@VDIAS I'm guessing you meant 2008 R2 to 2012 R2?

If so, then yes, IIS disappears and you have to install and configure IIS from scratch. There is no documentation over what roles can persist from 2008 R2 -> 2012 R2, so expect all roles and their configurations to disappear.

Roles CAN persist from 2012 R2 to 2019, and the documentation is here (it says 2016, but it's applicable for 2019 aswell): https://docs.microsoft.com/en-us/windows-server/get-started/server-role-upgradeability-table

Copper Contributor

@Kasper Jensen, no, i'm really talking about 2008R2 to 2008R2... i'm trying to restore all system packages and recover server health. Already done this procedure on others servers without problems, and it is the fastest and cleanest procedure to repair windows update errors.

 

This is the first server that have IIS role deployed and on which i needed to recover the server from previous backup.

 

 

Brass Contributor

@VDIAS As I said, there's no documentation for 2008 R2 regarding role compatibility, regardless if you're doing an upgrade repair (2008 R2 -> 2008 R2) or an actual upgrade. Searching around the web might get you to this page, or one of the other stock Microsoft documentation pages describing the general process. This article is for actual upgrades, and not upgrade repair, so better ask somewhere else.

Suffice it to say, IIS on 2008 R2 will die, no matter if you upgrade repair to 2008 R2, or actually upgrade to 2012 R2. Find other ways to get IIS back, like Web Deploy. I learned the hard way.

Copper Contributor

Thanks @Kasper Jensen !

Copper Contributor

Hi,

I have windows 2008R2 with OEM license, can I do an upgrade to 2019 Volume license version.

 

thank you 

Copper Contributor

Trying to do an in-place upgrade on a Server 2008 R2 to a Server 2016 is telling me that I cannot keep any files or data because you're upgrading from one windows version to another!

 

That would be a disaster...

 

Does anyone else get this? How can I get around that?

 

Thanks

Microsoft

@StylishJedi Did you upgrade to Windows Server 2012 first? You can only upgrade to 2016 from 2012 or 2012 R2.

Copper Contributor

@thomasmaurer Thank you for the article, it is very informative and helps me to understand the work that is in front of me to get my Windows 2008 R2 Web Server upgraded to 2019.

 

One question that I have for you is why you choose to use Windows 2012 R2 DataCenter edition instead of Windows 2012 R2 Server?

 

Does this matter at all since you are moving upward to 2019 anyway?

Sincerely

Copper Contributor

Thank You, Very useful content.. Please keep it up.

Copper Contributor

Can I do an in-place upgrade from Windows Server 2008R2 to 2012R2 then to Server 2016 without the need of an upgrade of the existing SQL server database that in place on Server 2008R2?

 

Copper Contributor

@MichaelHyde1280 @It depends which SQL server version you are using, there is a compatibility matrix available for SQL and OS. Recently I upgraded a VM from Windows 2012 R2 to 2019 with SQL 2012 SP3.

 

Thanks

Usman

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