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How To Install Server 2016 In Virtualbox

Published: December 1, 2025 (Updated: Dec 1, 2025)

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Mastering Your Test Lab: How to Install Windows Server 2016 on VirtualBox (Step-by-Step Guide)

Hi there! This is Darren from Darren’s Tech Tutorials, and I’m thrilled to guide you through setting up an essential piece of infrastructure today.

Whether you’re studying for an IT certification, testing out new features, or just want a safe environment to learn system administration, setting up a virtual server is the perfect solution. In this comprehensive guide, we’re going to walk through the entire process of installing Windows Server 2016 right inside Oracle VM VirtualBox.

VirtualBox offers a free, powerful way to run server operating systems without needing dedicated hardware. Let’s jump in and get your test environment built!

Prerequisites: What You Need to Get Started

Before we begin, make sure you have the following installed and available:

  1. Oracle VM VirtualBox: Installed and running on your host machine.
  2. Adequate System Resources: We recommend at least 4GB of RAM and two CPU cores free on your host machine to dedicate to the virtual server.
  3. High-Speed Internet: To download the Server 2016 ISO file.

Step 1: Downloading the Windows Server 2016 Trial ISO

Since we are creating a test environment, we will use the official free trial ISO provided by Microsoft. This is the first crucial step to ensure you have the necessary installation media.

  1. Search for the Trial: Open your web browser and search for “Windows Server 2016 free trial.”
  2. Navigate to Microsoft: Click on the official Microsoft result offering the free trial download.
  3. Select ISO: When prompted, ensure you select the ISO download type, as this is the file we need for VirtualBox.
  4. Enter Details and Download: Microsoft will prompt you to enter a few details (name, location, etc.). Fill out the form, select your desired language (English), and click Download.
  5. Save the File: Choose a location on your computer to save the ISO file. Note: This is a large file and may take several minutes to complete.

Step 2: Creating the Virtual Machine in VirtualBox

Once the download is complete, it’s time to prepare the container for the operating system within VirtualBox.

  1. Launch VirtualBox: Open the VirtualBox application.
  2. Click ‘New’: In the main menu, click the New button to start the Create Virtual Machine wizard.
  3. Name and Type:
    • Name: Enter a descriptive name, such as Windows Server 2016 Test.
    • VirtualBox should automatically detect the Type as Microsoft Windows and the Version as Windows 2016 (64-bit).
  4. Memory (RAM) Allocation: We need to give the server enough memory to run smoothly.
    • Set the memory size to at least 4096 MB (4 GB). If your host machine has limited RAM, you can use less, but be aware that performance will suffer.
  5. Hard Disk:
    • Select Create a virtual hard disk now.
    • Click Create.
  6. Hard Disk File Type: Leave the default setting (VDI - VirtualBox Disk Image). Click Next.
  7. Storage on Physical Hard Disk: Select Dynamically allocated. This means the virtual disk will only use the physical space it needs, up to the maximum limit we define next. Click Next.
  8. File Location and Size:
    • Set the file size to at least 50 GB.
    • Click Create.

Your new virtual machine container now appears in the VirtualBox dashboard!

Step 3: Configuring the VM Settings and Mounting the ISO

Before we hit the start button, we need to make two quick configuration tweaks: assigning an extra processor (optional, but helpful) and mounting the ISO file we downloaded earlier.

  1. Open Settings: Right-click on your newly created Windows Server 2016 Test VM and select Settings.
  2. Adjust Processor (Optional):
    • Navigate to the System category, then click the Processor tab.
    • If your host machine allows, slide the processor count up to 2 CPUs for better performance.
  3. Mount the ISO: This tells the VM to “insert” the installation disc (our ISO file).
    • Navigate to the Storage category.
    • Under the Storage Tree, select the empty CD icon next to the SATA Controller.
    • On the right-hand panel, click the small blue disk icon next to “Optical Drive.”
    • Select Choose/Create a Virtual Optical Disk… and locate the Windows Server 2016 ISO file you downloaded in Step 1.
  4. Confirm: Click Open, and then click OK to save the VM settings.

Step 4: Running the Windows Server 2016 Installation

We are ready for the final stretch—installing the operating system itself!

  1. Start the VM: Select your Windows Server 2016 Test VM and click the Start button in the main VirtualBox menu.
  2. Initial Setup Screen: The VM will boot from the ISO file. Once the setup screen appears, confirm your language, time/currency format, and keyboard input method. Click Next.
  3. Install Now: Click the big Install Now button.
  4. Product Key: Since we are using the trial version, click I don’t have a product key.
  5. Choose Your Edition: Select the Windows Server 2016 Standard (Desktop Experience) edition. The Desktop Experience ensures you have the graphical user interface (GUI) necessary for easy testing. Click Next.
  6. Accept License: Check the box to accept the license terms and click Next.
  7. Installation Type: Select Custom: Install Windows only (advanced).
  8. Select Drive: Select the 50 GB drive we created in VirtualBox and click Next.

The installation process will now begin, copying files and installing features. This will take some time and the VM will reboot automatically.

Finalizing Setup

  1. Password Prompt: After the final reboot, you will be prompted to set the Administrator password. Choose a strong, memorable password and enter it twice. Click Finish.
  2. Log In: The server will bring you to the lock screen. You can usually press Host Key + Delete (by default, the Right Ctrl key + Delete) to send the Ctrl+Alt+Delete command to the VM. Enter your new password to log into your brand new Windows Server 2016 Desktop!

Pro-Tip: If your mouse cursor gets stuck inside the virtual machine window, simply press the Right Control (Ctrl) key on your keyboard to release it back to your host operating system.

Ready to Master Your Server Environment!

And there you have it! You’ve successfully installed a fully functional Windows Server 2016 environment within VirtualBox. You now have a fantastic platform ready for testing, learning, and developing your system administration skills.

If this tutorial helped you get your lab set up, please hit the Like button and Subscribe to Darren’s Tech Tutorials for more clear, accessible technology guides. If you run into any snags during the process, drop a comment below—I’m always happy to help!

Happy learning!