Windows Server 2019 In-Place Upgrade Expert Guide

Is it the right time to move to a newer version of Windows Server? Depending on what you're running currently, you have lots of options to get there – upgrading being one of them. Windows Server 2016 can be upgraded to Windows Server 2019 in a single upgrade process. A Windows Server Upgrade doesn't have to be a complete overhaul or a new installation.

You can decide to keep the same physical hardware and all the already set-up server roles without pulling down the entire Server, a process called In-Place Upgrade. In an In-Place Upgrade, you go from an older version of the Operating System to a newer version, while keeping your data, server roles, and settings intact. In this article, you will learn how to conduct an In-Place upgrade from Windows Server 2016 to Windows Server 2019.

What should you know before upgrading to Windows Server 2019?

Server upgrades are not standard, and if you decided to upgrade, you must have a good reason to disrupt your otherwise smooth working environment. However, while Windows Server 2016 is still relatively young, their argument made for upgrading to a Server 2019 environment feels decent enough.

Remember that Windows Server 2016 was the first server OS to be built on the Windows 10 kernel. There are a few changes with Windows Server 2019. For starters, Windows Server 2019 is markedly faster and has some changes, ranging from security to hybrid cloud integration.

Windows server has never had the option of In-Place Upgrade until now, in Server 2019, which can be upgraded while keeping your installation configurations, Active Directory, settings, server roles and data in place, and so forth. Furthermore, Server 2019 also has Cluster OS Rolling Upgrade. This means as an administrator, you can upgrade the OS of your Server from Server 2012 R2 and Server 2016 without stopping easily.

All you need to do is ensure that in-place OS upgrades work for you or if you'll need a clean install. There are no changes in hardware requirements to change from Server 2016 to 2019, which make the in-place upgrade possible.

According to Microsoft, Windows Server 2019 heavily invested in better security and patching. Some significant new features and areas of improvement include Windows Defender ATP agent, Virtual network encryption, New Shielded VM improvements, and System Guard Runtime Monitor. Windows Defender Advanced Threat Protection (ATP), for instance, has received a significant upgrade to provide visibility into the kernel-level attacker and memory activities and the ability to act on compromised machines. Defender both detects and blocks ransomware and restores data and files if a ransomware attack.

There is also an improvement in storage and migration of storage that you can check before you decided to invest in the upgrade. Furthermore, Server 2019 also introduces improved support for Kubernetes. This is different from what Server 2016 had for Kubernetes, which was merely an add-on. Besides, Server 2019 can now run Ubuntu comfortably, as well as Red Hat Enterprise Linux, and SUSE Linux Enterprise Server inside shielded virtual machines.

Windows Server 2019 is also the first to support Azure Stack HCI. Microsoft released Azure Stack after the release of Server 2016, thus serve 2019 is the one that natively supports it. With Azure Stack, you can run the Azure-like cloud environment on your own hardware, which gives you an azure environment within your firewall. Also, Azure Stack is wholly integrated with Azure service, and it's now easy to move programs or apps between the two. Azure Stack HCI, part of the Azure Stack product, is exponentially better and significantly faster in Server 2019 performance-wise compared to 2016.

Other notable and significant features new to Server 2019 include system insights, unified management, storage class memory, and cluster-wide monitoring.

System Insights, for instance, brings predictive analytics capabilities, which are native to Windows Server, to enable better automation of server operations. This, in turn, helps to decrease the operational expenses that relate to reactively managing instances in Windows Server.
Storage class memory is a Server 2019-supported new-generation server hardware, which significantly improves the performance of the server applications.
Cluster-wide monitoring helps to monitor CPU and memory usage, throughput, storage capacity, latency, and IOPS in real-time and gives clear alerts in case of something is wrong.
Software-Defined Networking (SDN) support: SDN now provides a technique to configure and manage virtual and physical network devices centrally. Server 2019 adds the capability to monitor and manage virtual networks and subnets, connect virtual server machines to virtual serve networks, and generally monitor SDN infrastructure. Also, unlike Server 2016 which only supported IPv4, Server 2019 now supports IPv6 as well as dual-stack IPv4/IPv6 addressing as well.
Persistent memory support is an improved version operating in server 2019 and supports Intel's Optane persistent memory, which is simply an SSD with near-DRAM speeds. Now, Server 2019 offers non-volatile media byte-level access while also significantly reducing the latency of storing or retrieving data. This is good news.

While there are additions to Windows Server 2019, it is the norm of Microsoft that, during upgrades and new builds, it adds some features and removes some. The same has been applied in the Windows server 2019. Here is the list of features and functionalities that Windows has removed from Server 2019.

Print components
Internet Storage Name Service (iSNS)
Business Scanning (Distributed Scan Management)
Remote Desktop Virtualization Host and Remote Desktop Connection Broker in a Server Core installation

From all the described improvements and advantages, there's no reason to hold off Server upgrade from Server 2016 to Server 2019. If you want to migrate your workloads should do it right away.

Preliminary Preparation for In-Place Upgrade

Windows Server 2019 brings a lot of improvements, even though the changes are minimal. Thus, it is vital to put everything in order in preparation for the in-place upgrade. And sometimes, also though with very minimal chances, the upgrade may fail. Thus, before you start the Windows Server upgrade, it is recommended that you collect some specific information, particularly your devices, just for troubleshooting and diagnostic purposes. The collected data will only be used if the upgrade fails. Ensure that you store the collected information somewhere that you can get to it off of your device.

Have you set the target time frame for updating the Server? Setting the target time frame gives you the estimated time you need and what time your users will have to wait for the upgrade to be complete
Is the Server you're updating production-critical?
Does the upgrade have a scheduled maintenance window? The in-place upgrade should not be conducted during the same period as the maintenance window
Do you have enough time for a test upgrade on a similar or identical non-production server? Test upgrade is essential as it will help you calculate the target time frame and let you learn all the unique things you need to know before you commence the actual upgrade.
Who are the principal users of the Server you want to upgrade? Have you informed those that are using the Server – internal, external, or both – of the upgrade or maintenance? Do they know how long they've to wait?
Is there an accurate inventory of what is running on the Server? The inventory must elaborate on the following

Windows Server Features, settings and Roles
Microsoft applications: Exchange Server, SharePoint Server, SQL Server, etc.
3rd-Party applications: Oracle, DB2, SAP, etc.
Is the server part of a Failover Cluster?
Is the Server joined to an Active Directory domain?
Does the Server have any disk that is BitLocker protected?

How often is the currently running server backed-up? Sometimes backups come in the form of a scheduled maintenance window? So, you can go back and check if there is a scheduled maintenance window.
Have backups ever been successfully restored to the application or Server?
Which is the backup software for the current Server (Windows Server 2019)?
In case the In-place Upgrade fails, which would require rebuilding the Server, do you have access to the Windows Server and application install media? Is the media available? (Although it is highly minimal, In-place Upgrade can fail which necessitates ensuring that a plan is put in place for such a possibility, to maintain SLAs and minimize server downtime.)
Is the running server fully patched? (It is a strong recommendation to have the Server fully patched before starting the In-place Upgrade. Just in case a failure occurs, retrieving this information can support the restoration)
Run systeminfo.exe and ensure to save the output off of your device: on your system, open a command prompt, go to c:\Windows\system32, and while you're there, type systeminfo.exe. An image like this will appear on the screen; copy, paste, and store this system information off of your PC.

Run ipconfig /all and again save the output – resulting configuration information – in the same place as above:
Run Get-WindowsFeature and still keep the output as below:
Finally, run the Registry Editor (RegEdit), and capture the value of the HKEY_LOCAL_MACHINE\SOFTWARE\Microsoft\Windows NT\CurrentVersion key, this will show you the exact version (BuildLabEx) and Edition (EditionID) of Windows Server. You also need to copy, paste, and store the information as above.

Now you are ready for the upgrade before you proceed with the In-Place Upgrade

Ensure that you backup your device, including operating systems, virtual machines, and applications.
You MUST also Shut down, Live migrate, or Quick migrate any virtual machines that are running on the Server at the moment. During the in-place upgrade, you can't have any virtual machines running on the Server

All these are just security measures to ensure that the upgrade doesn't fail and that the process is smooth and less tedious. In simple terms, you must minimize the technical related errors as much as possible

How to Upgrade to Windows Server 2019 from 2016

First, you need to conduct one last check. Ensure that the value in the BuildLabEx confirms that you're running Windows Server 2016. Remember, you are performing an in-place Upgrade from windows server 2016 to windows server 2019. Thus, in case your current Server is 2012 then there are other procedures you will need to run before you commence the upgrade
Locate the Setup media for your Windows Server 2019.
Run the Setup. Double click the setup.exe to run it.
You will be prompted with a message to allow or deny the program to make changes to your computer. Click Yes to enable the Setup to proceed.
If your device is connected to the internet-connected, it is recommended that you select the Download updates, drivers, and optional features (recommended) option. You can also check the bottom left-hand corner of the screen to opt-in or out of the CEIP process. Then you select Next.
At this time setup will take a moment to check your device configuration – you need to wait. Check Next, when the configuration is complete.
Depending on the distribution channel that supplied your Windows Server media (Volume License, OEM, ODM, Retail, etc.) and the Server's license, you may see a screen prompting you to enter a licensing key. Enter the product key for you to continue with the Upgrade to Windows Server 2019.
You will see a screen prompting you to select the image of the Edition to upgrade to. The upgrade will then recognize the variant of the legacy Operating System you are coming from and present you with the correct option for upgrade. Since you are coming from Windows Server 2016, these are the options that will be presented. Select the Windows Server 2019 edition you want to install, and then select Next.
The next prompt is the typical EULA and notices from Microsoft. Depending on your distribution channel of Windows Server media, the license agreements often appear different. Click Accept:
A window will prompt you to choose what you want to keep during the upgrade. Since you are running and In-Place Upgrade, you need to keep personal files and apps. Select that option then click Next;
After clicking Next, an upgrade process will start checking for updates as was directed to do with the configuration options. This may not happen if the Server had been updated recently.
And, since this controls the domain, the in-place upgrade will recognize whether or not the domain has run the Forestprep and Domainprep processes. Forestprep will come first followed by domain prep
The method of running the domain prep and forestprep processes is similar as in previous generations. You will need to navigate the installation media to find the Support\adprep folder and use appropriate switches to run the adprep utility. First, run forestprep, and then domainprep.

$support\adprep$
As aforementioned, there the system will only have one schema file to extract and apply. Ensure that you see the forestprep process complete successfully.
Next, you will apply the domainprep process. It only takes a moment, and adprep shall have successfully updated the domain-wide information message. This will have made the actual upgrade process ready to run, consuming the earlier selected configuration in the upgrade wizard.
Setup will now analyze your device for readiness. When the analysis is complete, Setup will again prompt you to click Back to change choices (of what to keep) or proceed with the In-place Upgrade. Click Install:
The in-place upgrade starts immediately, on an Upgrading Windows screen showing its progress. After the upgrade finishes, and then the tour server will reboot.
Your set up will complete after some time, and your Windows Server 2019 will reboot several times to complete the upgrade. The screen will display "Working on updates" with a percentage until the process is complete.

Post Upgrade

After Setup completes installing successfully and the Server rebooted, login to check that the Server upgrade to Windows Server 2019 is successful. The image of the Windows Server 2019 Server Manager window appears like this:

You'll need to run the tun RegEdit and check the value of the HKEY_LOCAL_MACHINE\SOFTWARE\Microsoft\WindowsNT\CurrentVersion hive – and view the ProductName. You should also see the Edition of your upgraded Windows Server 2019, for example, Windows Server 2019 Datacenter.

Ensure that all of your applications are smoothly running and that your client connections to the applications are successful. This is an important check that you cannot forego.

If, for some reason, you feel there has been a hitch during the upgrade, copy and zip the %SystemRoot%\Panther (usually C:\Windows\Panther) directory then contact Microsoft for support.

Find anything you need

What should you know before upgrading to Windows Server 2019?

Preliminary Preparation for In-Place Upgrade

How to Upgrade to Windows Server 2019 from 2016

Post Upgrade