Windows Server

How to install Windows Server 2019 on Virtualbox

Oracle VM VirtualBox is a free and open-source hosted hypervisor for x86 virtualization, developed by Oracle Corporation. You may want to run multiple VMs on your operating system, with the type 2 virtualization type, this is possible. To achieve this, the following steps below need to be performed. To proceed, ensure you have VirtualBox installed on your device. On how to perform Post OS Installation configuration of Windows Server 2019 Properties, how to install Windows Server 2016 Operating System. Also, you may be interested in my YouTube video on how to setup Windows Server 2019 on a VMware Workstation. On how to install and configure Ubuntu Linux, see the visit link.

Part A: Prepare the Virtualbox environment to hold the windows folders for the new VM. Click on “New” from the Oracle VM VirtualBox Manager. See this guide for how to install Windows Server 2022 on VMware Workstation.

Enter the name, version, desired path to host the VMs and click on continue

Select the memory size as shown below. You can type in the memory size or use the bar to increase it as well.

Click on “create a virtual hard disk now”

This will open the hard disk type window as shown below.
– I will select VDI (Virtual Disk image)

Choose if you wish the hard disk to dynamically increase or use a fixed hard disk file size. I will be using a fixed size which will be entered in the next page

Enter the Hard Disk size of your choice as shown below
– You can also change the file location if you wish from here.

Next, this will create the VM as shown below

Now the VM creation process is complate and VM successfull created.

Part B: To access and attached the Windows Server 2019 ISO file, the following steps should be followed.

Click on the Server and Click or settings or
– Right click on the server and select settings

Click on storage
– Click on Empty under the control IDE
– Select the Disk icon and choose the Operating system you wish to install as shown below

As you can see below, the ISO image has been selected. We can now proceed with our installation.

– Click on “ok”. Next, select the VM and click on start to continue the installation of Windows Server 2019.

This will load windows and prompt for the steps in Part C below.

Part C: This step is similar to installing Windows 10, Windows Server 2008, 2012, 2016 on Virtualbox. On the Windows Setup page,
– Select the language to install
– Time and currency format
– Keyboard or input method

Click on Next and Click on “Install now

Note: Here you could click on repair your computer if this is the approach you need to take or use “Reset this PC”. See how to repair Windows 10 locally for similar steps. Select the operating system you wish to install and click on Next.

Accept the license agreement as shown below and click on next

Select custom install as shown below to install Windows
– Select Custom: Install Windows only (advanced)

Select the Drive to install Windows and click on Next
Note: You can create an additional drive and install Windows on it. You can also format, delete and extend drives in this window.

After this step, Windows will be installed unto the system.

When this step complete, the the device will reboot after few seconds
– Note: You can restart immediately

This will prepare and get windows ready as shown below

the customise settings window will be displayed. Enter the Password and click on finish to complete Windows Server 2019 Installation.

Now Windows Server 2019 setup is now complete as shown below.

To access the login windows, use the Contl+Alt+Del and enter your password to access Windows. Refer to this guide for the Post OS Installation and configuration of Windows Server 2019 Properties (Configure TCP/IP Parameters).

I hope you found this blog post helpful. If you have any questions, please let me know in the comment session.

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John L.
John L.
3 years ago

In my case (Desktop PC with Win 10, Build 1909) it did not work when choosing “Other Windows – 64 bit”, only when I choose “Windows Server 2016 – 64bit” the installation routine started.

Thanks anyway!

Emir Husic
Emir Husic
2 years ago

Now the VM creation process is complate and VM successfull created.

Now, the VM creation process has completed.

Sarah L
Sarah L
2 years ago

I just finished installing server 2019 onto a new virtual machine in Virtual Box.

After the initial restart, when it asks you to ctrl + alt + del to log in, this command is bringing up the ctrl+alt+del screen for the os virtual box is installed on, not the server running on the virtual machine.

What do I do?

1 year ago

Thank you Christian, this helped me get ready for a lab tomorrow 🙂

Max Krumholz
Max Krumholz
1 year ago

how to add the last version of oracle virtual box 6.1 ansible server?
have server 2019 have no option 64 bit in other only 32 bit

Max Krumholz
Max Krumholz
1 year ago

Ok Desktop PC Win 10 [Version 10.0.19043.1165) 19043.1165 – version 21H1 i download
from Oracle no ansible server on oracle virtual box 6.1 on Desktop Pc

Would love your thoughts, please comment.x