Windows Server 2019 In-Place Upgrade Expert Guide

When would you recommend upgrading to Windows Server 2016? There are a lot of ways to get there, including upgrading, which depends on what you are now running. It is possible to upgrade from Windows Server 2016 to Windows Server 2019 all at once. It is not necessary to reinstall Windows or perform a total overhaul in order to upgrade Windows Server.

Without taking the server down, you can upgrade it and keep all of its current features and hardware. Upgrading operating systems using an in-place update keeps all of your data, roles, and configurations intact, allowing you to go from an earlier version to a newer one. Here, you will find detailed instructions on how to update Windows Server 2016 to Windows Server 2019 in place.

Before you upgrade to Windows Server 2019, what information is necessary?

It takes a compelling cause to decide to upgrade your Server, as it is not a common practice. Otherwise, your otherwise smooth working environment will be disrupted. Their case for moving to Server 2019 seems reasonable, even if Windows Server 2016 is still in its early stages.

Keep in mind that the first server operating system to be based on the Windows 10 kernel was Windows Server 2016. Windows Server 2019 has a few new features. To begin, Windows Server 2019 is much quicker and contains several updates covering topics like security and the integration of hybrid clouds.

With Windows Server 2019, an In-Place Upgrade option is now available, allowing you to upgrade the operating system while preserving your installation settings, Active Directory, data, server roles, and customizations. Furthermore, Server 2019 offers Cluster OS Rolling Upgrade. This allows a server administrator to easily upgrade from Server 2012 R2 to Server 2016 without affecting the Server’s availability.

Verify if an in-place OS upgrade is an option or if a fresh installation is necessary. That is all. The ability to upgrade in place from Server 2016 to 2019 is due to the fact that the hardware requirements have not changed.

Windows Server 2019 had a significant focus on security and patching, as stated by Microsoft. Virtual Network Encryption, Windows Defender ATP agent, New Shielded VM, and System Guard Runtime Monitor are some of the new features that stand out. Consider Windows Defender’s Advanced Threat Protection (ATP). It has been significantly improved to allow the attacker to see what the system is doing at the kernel level, access memory, and take control of infected devices. Defender can do more than just identify and fight ransomware; it can also restore data and files in case of an attack.

Before deciding to upgrade, you may also check if there are any improvements to storage or migration of storage. Improved support for Kubernetes is another new feature in Server 2019. This is in contrast to the optional support for Kubernetes in Server 2016. In addition, Ubuntu, Red Hat Enterprise Linux, and SUSE Linux Enterprise Server can now be run comfortably inside shielded virtual machines in Server 2019.

Windows Server 2019 will also see the debut of Azure Stack HCI. Since Microsoft released Server 2019 following Server 2016, it has been the first edition to offer native support for Azure Stack. With Azure Stack, you may run a cloud environment similar to Azure on your own hardware. An Azure environment can be housed within your firewall in this way. The tight connectivity between Azure Stack and Azure service has also made it simple to move apps and programs between the two. When comparing the performance of Azure Stack HCI in 2016 with that of Server 2019, the performance gap is enormous, and the speed difference is substantial. 

New to Server 2019 are storage class memory, system insights, unified management, and cluster-wide monitoring, among other noteworthy and important improvements.

• System Insights, for example, delivers predictive analytics capabilities that are intrinsic to Windows Server to further automate server operations. Consequently, this contributes to a reduction in the operating costs associated with reactively managing instances in Windows Server.
• Server 2019 is compatible with storage class memory, a type of next-gen server hardware that greatly enhances application performance on the Server.
• In the event that anything goes wrong, cluster-wide monitoring can provide clear alerts and real-time monitoring of CPU and memory consumption, throughput, storage capacity, latency, and IOPS.
• Software-Defined Networking (SDN) Integration: SDN provides a way to manage and configure virtual and physical network devices centrally. Updated capabilities in Server 2019 allow you to monitor software-defined networking (SDN) architecture, administer virtual networks and subnets, and connect virtual servers to virtual networks. Additionally, Server 2019 now supports IPv6 and dual-stack IPv4/IPv6 addressing, in contrast to Server 2016, which solely supported IPv4. 
• Support for Intel’s Optane persistent memory—a simple solid-state drive (SSD) with near-DRAM speeds—is an upgraded version that runs on the 2019 server. In addition to drastically cutting down on latency, Server 2019 now provides byte-level access to non-volatile media. This is encouraging news.

Windows Server 2019 does have some new features, but it is typical for Microsoft to add some and delete some with updates and new builds. Similarly, Windows Server 2019 has implemented this. The following is a rundown of the capabilities and features that Windows has disabled in Server 2019.

• Create parts
• Name Service for the Internet Storage (iSNS)
• Distributed Scan Management for Business Scanning
• Two components of Server Core that facilitate remote desktop virtualization are the host and the connection broker.

After reading about all the new features and enhancements, you will not want to wait to upgrade your Server from 2016 to 2019. You should immediately begin migrating your workloads if you so desire.

Groundwork for On-Site Improvement

Despite the little modifications, Windows Server 2019 provides numerous improvements. That is why getting ready for the in-place upgrade is so important. Additionally, the update may fail on rare occasions, albeit this is far from the norm. So, for diagnostic and troubleshooting reasons, it is essential that you gather some specific information, especially about your devices, before you begin the Windows Server upgrade. Unless the upgrade fails, the data acquired will be discarded. You should make sure that you can access the data stored elsewhere when you are not using your device.

• When will the Server be updated? Have you decided when? When you set the desired time period, you will know how long the upgrade is expected to take and how long your users will have to wait.
• Is the Server that needs updating a priority in terms of production?
• I was wondering whether there was a maintenance window for the upgrade. You should not do the in-place upgrade when the maintenance window is open.
• Can you spare the time to upgrade a non-production server that is functionally equivalent to the production server? Before beginning the actual upgrade, it is vital to conduct a test upgrade to determine the desired time frame and discover all the unique aspects you need to know.
• Before you upgrade the Server, who are its primary users? Is the upgrade or maintenance known by everyone who uses the Server? I mean, both internal and external users, right? Are they aware of the wait time?
• Does one have a complete list of all the processes that are active on the Server? There needs to be more detail in the inventory about the following:
• • Accounts, preferences, and settings in Windows Server
  • Microsoft software: SQL Server, Exchange Server, SharePoint Server, and more.
  • Other applications include Oracle, DB2, SAP, and so on.
  • Remember how the Server is like a node in a failover cluster?
  • Am I correct in assuming that the Server is an Active Directory domain member?
  • Is there a BitLocker-secured disc on the Server?
• At what intervals is the Server currently actively backed up? Backups can also take the shape of a prearranged maintenance window. Therefore, you can return to the page to see if a maintenance window has been scheduled.
• Is it true that you have restored backups to the Server or application before?
• In the case of the present Server (Windows Server 2019), which software is used for backup purposes?
• Have you got the Windows Server and application installation discs on hand in case the in-place upgrade does not work and the Server needs to be rebuilt? Can I access the media? (Even though it is very unlikely, In-place Upgrades can fail. To keep service level agreements (SLAs) and server downtime to a minimum, you should prepare for this possibility.)
• Has every patch been applied to the Server that is now running? It is highly advised that the Server be completely patched prior to commencing the in-place upgrade. If something goes wrong, getting this data can help with the repair.
• Execute systeminfo.exe and be sure to save the device’s output: Launch a command prompt on your computer, navigate to c:\Windows\system32, and then type systeminfo.exe. You can save this system information from your computer by copying and pasting the image that appears on the screen.

• • Once again, run ipconfig /all and save the output (the configuration information that comes out) in the same location as before:

• • Keep the following output while running Get-WindowsFeature:
• 
  • Launch the Registry Editor (RegEdit) and paste the value of the HKEY_LOCAL_MACHINE\SOFTWARE\Microsoft\Windows NT\CurrentVersion key to discover the precise version (BuildLabEx) and Edition (EditionID) of Windows Server. Pasting, copying, and saving the data is required, as before.

Your preparations for the update are complete; the next step is to implement the in-place upgrade.

• Do not forget to create a backup of your device’s operating system, software, and virtual machines.
• Additionally, you are obligated to power down, live migrate, or quickly migrate any virtual machines that are currently operating on the Server. There must be no virtual machines operating on the Server during the in-place upgrade.

These are all precautions taken to make sure the upgrade goes through without a hitch and to make the process easier and less laborious for you. Put simply, you need to make sure that technical faults are minimized to the maximum extent possible.

Getting From Windows Server 2016 to Windows Server 2019

• Verify that you have ticked all the boxes before proceeding. Verify Windows Server 2016 by checking the BuildLabEx value. As you upgrade from Windows Server 2016 to Windows Server 2019, remember that the process is painless. So, if your current Server is 2012, you’ll need to take extra precautions before you start the update.
• The Windows Server 2019 installation disc should be located somewhere.
• Start the Setup. Launch it by double-clicking the setup.exe file.

• A message asking if you want to authorize the application to make changes to your computer will appear. In order to proceed with the Setup, click Yes.
• Pick the “Download updates, drivers, and extra features (recommended)” option if your gadget can access the internet. To toggle the CEIP on or off, look in the lower-left corner of your screen. After that, you just click the “Next” button.

• Lay tight for a second while setup checks your device’s settings. Once the Setup is finished, click Next.

• A screen asking for a licensing key may appear when installing Windows Server, depending on the distribution channel (Volume License, OEM, ODM, Retail, etc.) and the license of the Server. Please input your product key so that you may proceed with the Windows Server 2019 Upgrade.

• An image of the Edition you wish to select will appear on the screen. When the update is ready to install, you’ll be asked to choose the version of the legacy OS you’re using. These options will be shown to you because Windows Server 2016 was your prior operating system. Click the Next button once you’ve decided on the Windows Server 2019 installation version.

• After this, you’ll see the usual Microsoft notifications and the end user license agreement. Depending on the distribution method, the license agreements for Windows Server media can differ. After that, click “Accept“:

• During the upgrade, a popup will appear, asking you to select which items to keep. You should retain your own data and applications while conducting the In-Place Upgrade. Pick that one and then press the Next button;

• Clicking Next will initiate an upgrading process that checks for updates, following the instructions provided in the configuration settings. A recent update to the Server might prevent this from happening.

• Also, the in-place upgrade can tell if the domain has executed Forestprep and Domainprep because this is the domain controller. Prior to domain preparation, forest prep will be completed.

• Following previous versions’ protocols, both the domain prep and forest prep processes are repeated. You need to find the Support\adprep folder on the installation disc and then use the correct switches to run the Adprep software. Prior to executing domainprep, run forestprep.

• There will be just one schema file for the system to use, as described earlier. Verify that the forest prep procedure finishes without a hitch.

• The message that is accessible to everyone on the domain will be altered by adprep after a short while. The domain prep procedure is the next step. After a short while, adprep will have changed the message that is visible to everyone on the domain. The next step is to use the configuration that was previously selected in the upgrade wizard to start the upgrading process.
• At this point, Setup will determine whether your gadget is ready to go. Setup will ask you to click Back once again to adjust the options (what to preserve) or to continue with the in-place upgrade after the analysis is finished. Roll out the software:

• A Modernization As soon as the in-place upgrade starts, a Windows screen will appear to show you the status. After the upgrade is finished, the tour server will restart.
• Windows Server 2019 will reboot multiple times during the installation process, but it will finish updating in the end. “Working on updates” will be shown on the screen along with a percentage until the procedure is finished.

Following the Transition

After the server has rebooted and the setup has been completed, install Windows Server 2019 and log in to the system to verify the update went smoothly. The Windows Server 2019 Server Manager window may be seen in this screenshot:

To inspect the ProductName, launch RegEdit and confirm the value of the HKEY_LOCAL_MACHINE\SOFTWARE\Microsoft\WindowsNT\CurrentVersion hive. Your Windows Server 2019 Datacenter, or an equivalent upgraded version, should also be visible.

If you want to be sure everything is running well with your apps, you should check that your client connections are successful. This is an essential check that you must not miss.

After you have copied and zipped the %SystemRoot%\Panther (typically C:\Windows\Panther) directory, contact Microsoft for assistance if you think an issue happened during the update.