Install Windows 2019 Server (LTSC & SAC) on VirtualBox with ISO/VHDX

It is always advisable to install and test the new Operating Systems in the virtual platform before trying in a live environment, especially the server version which we use in the production. In this guide, let me shows the steps I followed to install Windows 2019 server LTSC and SAC versions on Oracle VirtualBox.  The Windows 2019 server OS was built on the firm foundation of the earlier Windows 2016 server. Windows 2016 was the popular and fastest adopted Windows server Operating System ever, and Microsoft is expecting the 2019 version to overtake it.

To learn more about what is new in Windows 2019 server version, you can check here. As a Windows server administrator or a learner you would love the new features it brings up.  The project Honolulu is something I’m incredibly interested in and happy to have.

Two Versions of Windows 2019

You must understand the significant difference between both Windows 2019 versions. I have shown the way of installing both Semi-Annual Channel (SAC) and Long-Term Servicing Channel (LTSC) on VirtualBox with my Windows 10 computer. Find below the major differences between both versions.

1) Semi-Annual Channel (SAC)

  • It gets feature updates from Microsoft twice a year. Your organization should have Software Assurance to be eligible for the upgrade.
  • The Windows 2019 SAC doesn’t have GUI. So, it is like Windows Server Core or Nano installation. It is well secured and optimized, but management is not easy without GUI.

2) Long-Term Servicing Channel (LTSC)

  • It is for the organizations that prefer the more traditional release of feature updates in two to three years.
  • It comes with both Server Core and Desktop Experience (GUI) versions.

Let’s dive into the installation of the Windows 2019 server on VirtualBox.

I already published a guide showing how to install Windows 2012 R2 on VirtualBox with a pre-installed VHD file from Microsoft. At the moment, Microsoft Provides ISO and VHD files of the Windows 2019 server on their official website.

To continue further, you must be able to download the Windows 2019 ISO file from the Microsoft Windows Insider Program website. It will help if you have a Windows live account that is part of the Insider program (Free to join). Here is the URL to download Windows 2019 server version for testing and demo installation purposes.

Windows 2019 Server VHDX on VirtualBox

Unfortunately, I could not use the VHDX file of both Windows 2019 SAC and LTSC versions on the VirtualBox. VirtualBox was unable to read the VHDX file properly. Therefore it can’t be used to boot the virtual machine from it.

It threw the following error while attaching the VHDX, “Failed to open the disk image file..” with the “MediumWrap” “E_FAIL”. It is still doubtful whether VHDX is supported in VirtualBox for reading and writing access. It looks like it supports only read-only as of now. As you are aware, VHDX files are mainly made for Microsoft Hyper-V hypervisor.

The Error Message When Open VHDX

VHDX to VHD

I used “vboxmanage clonemedium” command to convert the VHDX to VHD, it succeeded and converted the Windows 2019 Server VHDX to VHD. Also, this time I managed to add the converted VHD disk to the new Virtual Machine. But it did not boot. It gave the error saying the “No Bootable medium found.” To reconfirm the readability of the converted VHD file, I attached the disk to another working Windows VM and managed to read the content on the VHD file. I’m yet to find the solution in mounting the preinstalled Windows 2019 Server VHDX on VirtualBox and see how it works.

At the moment, the final solution is to use the ISO file and do the fresh installation.

Windows 2019 Semi-Annual Channel (SAC) on VirtualBox

It worked, but I’m not sure why you need to install a Server Core version in VirtualBox without Desktop experience. But for a full-fledged test lab setup, you can install in multiple VMs to test the feature of the Windows 2019 server cluster and server farm.

I assume that you have already worked on the Server Core version. The installation is simple and straightforward. Download the ISO file of Windows 2019 SAC from Microsoft and start installing.

1. Select the Operating System as “Windows 2016” or Windows 2019 based on the version of the Oracle VirtualBox you have.

Select The OS Version2. Make sure that Processor settings remain the same as below. By default when you select the Windows 2016 version, it sets automatically.

Processor Settings3. Set the RAM; I allocated 4GB RAM and 50GB new hard disk.

4. Attach the downloaded ISO and start the Virtual Machine.

Added Windows 2019 ISO5. Select either “Standard” or “Data Center” version to install. I selected the Data Center version and continued the installation.

6. Once installation is completed, you will get the first screen to set an administrator account. It is going to be the server core version; you need to play with the command prompt and PowerShell. Mouse and keyboard integration works fine.

7. With the ‘sconfig’ command you can configure the Windows 2019 Core on VirtualBox.

Windows 2019 Server Core On VirtualBox8. Network worked without installing VirtualBox additions inside VM (NAT type, it should work with any type including Bridged or Internal only).

Working Network Inside VM Windows 2019 Server Core

We do not need to install guest additions on this Server Core since it doesn’t have a desktop graphical interface.

Windows 2019 Long-Term Servicing Channel (LTSC) on VirtualBox

The LTSC version of Windows 2019 Standard and Datacenter have both Desktop experience GUI and core installation. Here I selected the Datacenter with the desktop experience.

9. The installation steps are the same as the SAC server mentioned earlier. Select the correct version you want to test with the Desktop experience as mentioned

Desktop Experience On Windows 2019 Server10. You can leave the OS key; this will enable your evaluation period once the installation is completed. You need to set a new complex password for the Administrator account. You will land on the Windows 2019 server desktop which is almost identical to Windows 2016 and 2012 R2 versions.

Below is the first screen without VirtualBox guest additions. You can see the space between the console and Windows 2019 virtual machine desktop because no guest additions were installed hence the auto-size of the display not working.

Desktop Without VB Additions

11. Click on Devices and mount the guest additions as shown below.

Mount Guest Additions12. It will be as the DVD disk inside the VM. Open it and execute the 64-bit version (even you can execute the normal one which will detect the OS and install the appropriate version).

Windows 2019 server on VirtualBox with guest additions13. Click yes to install if the warning comes as not a trusted driver.

Trust The Application14. Reboot the VM after completion.

15. Once it is rebooted and logged in, you will see a better display, mouse integration and performance enhancement inside the VM. Also, the auto display re-size will work fine.

Take a snapshot before you do any changes from this point.

There you go, you have both versions of the Windows 2019 server (LTSC and SAC) on your Windows 10 desktop or laptop by using Oracle VirtualBox. Hope this guide is useful for the testing or demo lab setup at home/office.

Dinesh is the founder of Sysprobs and written more than 400 articles. Enthusiast in Microsoft and cloud technologies with more than 15 years of IT experience.

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