Upgradation 2019

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 particular 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.how to run system information on windows server

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

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 downLive 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

  1. 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
  2. Locate the Setup media for your Windows Server 2019. 

Run the Setup. Double click the setup.exe to run it.

  1. 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) optionYou 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

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.disk image

Depending on your distribution channel of Windows Server media, the license agreements often appear different. Click Accept:in place windows server 2019 upgrade

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


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

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

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:installing windows server 2019

  1. 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 completed.

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.