How to Install Windows Server 2019 in VirtualBox (Step By Step Guide)

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Published on Sep 19, 2025 This response is partially generated with the help of AI. It may contain inaccuracies.

Table of Contents

Introduction

This tutorial will guide you through the process of installing Windows Server 2019 Datacenter Evaluation Edition in Oracle VirtualBox. By following these steps, you'll set up a virtual server environment, which is ideal for testing and learning purposes.

Step 1: Check System Requirements

Before starting the installation, ensure your system meets the necessary requirements to run Windows Server 2019.

Step 2: Download Windows Server 2019 ISO

You will need the Windows Server 2019 Evaluation ISO file to proceed with the installation.

  • Go to the Microsoft Evaluation Center: Download Windows Server 2019.
  • Select the appropriate version and download the ISO file to your computer.

Step 3: Install Oracle VirtualBox

If you don't already have Oracle VirtualBox installed, follow these steps:

  1. Visit the VirtualBox website and download the latest version for your operating system.
  2. Run the installer and follow the on-screen instructions to complete the installation.

Step 4: Create a New Virtual Machine

Now, you will create a new virtual machine in VirtualBox.

  1. Open Oracle VirtualBox.
  2. Click on "New" to create a new virtual machine.
  3. Enter a name for your virtual machine (e.g., "Windows Server 2019").
  4. Set the type to "Microsoft Windows" and version to "Windows 2019 (64-bit)."
  5. Allocate memory (RAM) to the virtual machine (minimum 2048 MB recommended).
  6. Create a new virtual hard disk:
    • Choose "VDI" (VirtualBox Disk Image).
    • Select "Dynamically allocated."
    • Set the disk size (minimum 20 GB recommended).

Step 5: Configure the Virtual Machine Settings

Before starting the installation, configure the settings of the virtual machine.

  1. Select the newly created virtual machine and click on "Settings."
  2. Under "System," ensure that "Enable EFI" is checked if you want to use UEFI.
  3. Go to the "Storage" section:
    • Click on "Empty" under Controller: IDE.
    • On the right, click the disk icon and select "Choose a disk file."
    • Locate and select the downloaded Windows Server 2019 ISO file.
  4. Adjust network settings if necessary (NAT or Bridged Adapter depending on your needs).

Step 6: Start the Virtual Machine

You are now ready to start the installation process.

  1. With your virtual machine selected, click on "Start."
  2. The virtual machine will boot from the ISO file.
  3. Follow the installation prompts:
    • Select your language, time, and keyboard preferences.
    • Click "Next," then "Install now."

Step 7: Choose Installation Type

You will need to select the type of installation.

  • Select "Windows Server 2019 Datacenter (Desktop Experience)" for a full installation with a GUI.
  • Click "Next," then accept the license terms.

Step 8: Create a Partition

During installation, you will need to create a partition for Windows Server.

  1. Select the unallocated space and click "New" to create a new partition.
  2. Click "Apply" to create the necessary partitions.
  3. Select the primary partition and click "Next" to continue.

Step 9: Complete the Installation

Allow the installation process to complete. This may take some time, and your virtual machine will restart several times.

  • After the final restart, you will be prompted to set up the administrator account.
  • Enter a password and complete any additional configuration steps.

Conclusion

You have successfully installed Windows Server 2019 in Oracle VirtualBox. This setup allows you to explore server features and functionalities in a safe environment. For further learning, consider configuring roles and features, or testing server applications. Happy exploring!