Как обновить windows server 2008 r2 до windows server 2019 r2

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 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:infosysteminfo.txt
ipconfig /all > C:infoipconfig.txt

Please copy and save the systeminfo.txt and ipconfig.txt file on another system.

Windows 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.

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.

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 Systeminfo

If there has been an issue with the upgrade, make a copy and zip the %SystemRoot%Panther (usually C:WindowsPanther) 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 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 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

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

Windows Server 2019 license terms

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

Windows 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

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

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:WindowsPanther) 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.

Windows Server 2008/2008 R2 have reached the end of support from Microsoft as of January 14, 2020. Running an in-place upgrade on Windows Server 2008/2008 R2 will allow upgrading to newer versions of Windows Server. Let’s see what the process looks like to run a Windows Server 2008/2008 R2 in-place upgrade to Windows Server 2019.

As most are aware, support for Windows Server 2008/2008 R2 has ended as of January 14, 2020. This means that if you have any Windows Server 2008/2008 R2 hosts running in your environment, you are currently in an unsupported state. There are many great options out there for migrating away from Windows Server 2008/2008 R2. In this post, we will focus on Windows Server 2008/2008 R2 in-place upgrade and see what this involves.

Windows Server 2008/2008 R2 migration options

To take a step back for a moment, there are a few options to get from Windows Server 2008/2008 R2 to a supported version of Windows Server. What are these options? When does an in-place upgrade make the most sense? The following are viable options for moving your production services and data to a supported version of Microsoft Windows Server:

• Migrate your on-premises Windows Server 2008/2008 R2 server to Azure
• Use Windows Server Storage Migration
• In-place upgrade

Migrating on-premises Windows Server 2008/2008 R2 server to Azure

Microsoft is dangling a carrot in front of businesses that may have production workloads still running inside Windows Server 2008/2008 R2 deployments. If you migrate these on-premises workloads to Azure, you will get another three years of extended security updates. Not only do you get three more years of updates and support, but it is free aside from the Azure cost.

This can be a good option for some who may already have a presence in Azure and who want the simplicity of rehosting the same exact server inside Azure. With free security updates, this allows much more time for deciding on a migration plan or refactoring of applications.

Three years of extended upgrade free when migrating to Azure (image courtesy of Microsoft)

Using Windows Server Storage migration

Windows Server Storage Migration is another option that allows using Windows Admin Center and the Windows Server Storage Migration module to migrate from a Windows Server 2008/2008 R2 platform to a supported platform such as Windows Server 2019.

Using Windows Server Storage Migration, you can completely move your data, permissions, and users and assume the identity of the server in an automated fashion; the heavy lifting is done for you. This enables easy migration of file servers running on legacy platforms up to a supported version of Windows Server.

Using the Storage Migration Service to migrate from Windows Server 2008

In-place upgrade

An in-place upgrade allows mounting the installation media for a newer version of Windows Server and running through the upgrade process on the legacy server. The Windows Server installation setup recognizes that an existing version of Windows Server is installed and will prompt you to choose between a clean installation or an upgrade. If an upgrade is chosen, the existing operating system, settings, and data are migrated (best effort) to the newer platform.

Windows Server 2008/2008 R2 in-place upgrade

There may be cases in which you simply want to keep your Windows Server 2008/2008 R2 server on-premises and upgrade it to a supported version of Windows Server and keep existing application installations in place. In this case, the in-place upgrade will most likely be the easiest option.

Upgrade path

It is important to note the upgrade path from Windows Server 2008/2008 R2 to newer Windows Server operating systems, such as Windows Server 2019. The below infographic from Microsoft helps to visualize the upgrade paths from Windows Server 2008/2008 R2 to Windows Server operating systems such as Windows Server 2012/2012 R2, Windows Server 2016, and Windows Server 2019.

Windows Server in-place upgrade to current versions of Windows Server (image courtesy of Microsoft)

If you want to perform an in-place upgrade from Windows Server 2008/2008 R2 all the way up to Windows Server 2019, what does the process look like?

You will need to perform two in-place upgrade processes. Since you can’t perform an in-place upgrade directly from Windows Server 2008/2008 R2 to Windows Server 2019, you have to first upgrade to Windows Server 2012 R2 and then perform an in-place upgrade to Windows Server 2019.

Windows Server 2008/2008 R2 in-place upgrade process

Before actually running the in-place upgrade from Windows Server 2008/2008 R2 to a newer version of Windows Server, it is best practice to audit your legacy Windows Server. It is important to consider the following:

• What roles and features are installed? Do these exist in the target version of Windows Server?
• What software and software components are installed? Are there supported versions for these in the target version of Windows Server?
• Do you have a good backup of the server? Other than creating a snapshot/checkpoint (if virtual), be sure to have a proper backup of the server.
• Do you have enough free space on your system drive to perform the upgrade? In-place upgrades require additional available free space to be successful.
• Start with the latest patch version available for your current legacy server. This helps to ensure you have the most current updates and patches available to ensure the in-place upgrade is successful.
• Test the upgrade in a lab environment if possible

Once you have considered these items and others that may be important for your particular environment, you should be able to begin the in-place upgrade.

Below is a screenshot of the Windows Setup dialog box, which opens when you run the Windows Server 2012 R2 installation media from a Windows Server 2008/2008 R2 server. Click Install Now.

The upgrade includes screens asking about pulling the latest updates, entering the license key for Windows Server 2012 R2, and choosing the operating system you want to install.

You will eventually see the screen to choose which type of installation you want to install. Here, choose Upgrade: Install Windows and keep files, settings, and applications.

After you click the Upgrade option, you will see the normal Windows installer screens that retain your settings and update your Windows Server installation. Your server will reboot several times.

Once the upgrade process has completed, you will see the freshly upgraded Windows Server 2012 R2 installation. It should contain your previous apps, data, and settings.

Now, if Windows Server 2012 R2 is not your final destination, you will need to perform another in-place upgrade to reach your target Windows Server version.

As you recall, we have to perform this same process over again to get from Windows Server 2012 R2 up to Windows Server 2019. After mounting the Windows Server 2019 install media on the newly upgraded Windows Server 2012 R2 server, we run the upgrade again. The installer will prompt you to download updates to the installer itself.

You will need to enter a valid Windows Server 2019 license key and also select the Windows Server 2019 image you would like to install.

The wording of the upgrade vs. clean install with the Windows Server 2019 installer is a bit less obvious. On the Choose what to keep page, select Keep personal files and apps for an upgrade. Select Nothing if you want to perform a clean installation.

You will want to choose the first option for an upgrade.

The upgrade is ready to proceed with keeping your files and applications.

Just as with the upgrade to Windows Server 2012 R2, the server will reboot several times. After a short time, your server should successfully upgrade to Windows Server 2019.

Conclusion

With the end of support from Microsoft for Windows Server 2008/2008 R2 reached as of January 14, 2020, moving production workloads off Windows Server 2008/2008 R2 should be a priority. While there are several ways to move your workloads to newer versions of Windows Server, the in-place upgrade may be the best option for those who want to keep their server on-premises and who have many custom applications, settings, and data that would be difficult to migrate to a different server.

The Windows Server 2008/2008 R2 in-place upgrade to Windows Server 2019 involves two in-place upgrades: one to Windows Server 2012 R2 and then an upgrade from 2012 R2 to Windows Server 2019. All in all, the process is straightforward and should be easy to accomplish with planned down time.