DTT

How to install Server 2019

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

Enjoying this content? Subscribe to the Channel!

The Ultimate Step-by-Step Guide to Installing Windows Server 2019 (VirtualBox or Physical Machine)

Hi there, tech enthusiasts! Darren O’Neill here from Darren’s Tech Tutorials. Today, we’re diving into the heart of modern enterprise networking: Windows Server 2019.

Server 2019 is a robust and powerful operating system, and getting it installed is the first step on your journey to mastering system administration. In this comprehensive guide, I’ll walk you through the entire installation process.

While I will be demonstrating this installation inside a virtual environment using VirtualBox, rest assured that the steps for installing it on a physical machine are essentially the same—you’ll just need to burn the installation image onto a DVD or USB drive instead of mounting it virtually.

Let’s get started!

1. Securing the Windows Server 2019 ISO

Before we can begin the installation, we need the installation file—the ISO image.

A Quick Note on Downloads: Microsoft periodically updates its download locations for evaluation copies. If you run into trouble finding the official evaluation ISO due to temporary bugs or redirects, you might need a direct link.

For a full text tutorial and the currently available download link for the Windows Server 2019 ISO, please reference the full resource here:

https://darrenoneill.eu/?p=1521

Once you have the ISO file downloaded, you’re ready to proceed!

2. Setting Up Your Virtual Machine in VirtualBox

If you are installing on a physical server, you can skip to Step 4. If you are following along in a virtual environment, we need to create the new server container first.

If you don’t already have it, VirtualBox is a free, popular hypervisor tool that lets us run virtual operating systems.

Creating the Virtual Machine

  1. Open VirtualBox and click the New button.
  2. Name: Call the machine Server 2019. VirtualBox should automatically adjust the type to Microsoft Windows.
  3. Type: Select Microsoft Windows.
  4. Version: Select Windows 2019 (64-bit).
  5. Memory (RAM): For this test environment, I recommend allocating at least 2048 MB (2 GB) of RAM.
  6. Click Next.

Creating the Virtual Hard Disk

We now need to assign storage space for our new server.

  1. Select Create a virtual hard disk now.
  2. Choose the default VDI (VirtualBox Disk Image) and keep the default selection for Dynamically allocated (this saves space on your host machine).
  3. File location and size: For testing purposes, 20 GB is sufficient. Click Create.

3. Mounting the Server 2019 Installation Media

Now that the virtual machine exists, we need to tell it where the installation files are.

  1. Right-click on your newly created Server 2019 VM in the VirtualBox list and select Settings.
  2. In the Settings window, navigate to Storage.
  3. Under the Storage Tree, select the Empty CD icon under the Controller: IDE section.
  4. On the right-hand side, click the smaller CD icon next to “Optical Drive.”
  5. Select Choose a disk file… and navigate to where you saved the Windows Server 2019 ISO file. Select it and click Open.
  6. Click OK to close the Settings window.

The ISO is now mounted! Click Start to boot up your new virtual server.

4. The Windows Server 2019 Installation Walkthrough

Once the virtual machine boots up (or your physical machine boots from the USB/DVD), the steps are identical.

Step 1: Initial Setup

  1. The Windows Setup screen will appear. Select your Language, Time and Currency format, and Keyboard input. For most users, leaving the defaults is fine.
  2. Click Next, then click Install now.

Step 2: Selecting the Installation Type

You will be prompted to choose the edition of Windows Server you wish to install.

Crucially, you must select the Desktop Experience version if you want a graphical interface (GUI).

  1. Select Windows Server 2019 Standard (Desktop Experience) or Datacenter (Desktop Experience), depending on your needs.
  2. Click Next.

Step 3: Licensing and Drive Selection

  1. Read through the license terms and check the box to Accept the license agreements. Click Next.
  2. When asked “Which type of installation do you want?”, select Custom: Install Windows only (advanced).
  3. You will see your 20 GB hard drive listed. Select this drive and click Next.

Windows will now begin copying files and installing the necessary features. This process takes a few minutes, so grab a coffee! The machine will reboot several times during this phase.

Step 4: Finalizing the Account

Once the installation is complete, you will be prompted to set the password for the built-in Administrator account.

  1. Enter a strong password that meets the complexity requirements.
  2. Re-enter the password to confirm.
  3. Click Finish.

Congratulations! Windows Server 2019 is now installed and ready for its initial login.

5. Logging In

Since you are running this virtually, you might need to use the VirtualBox shortcut to send the familiar CTRL+ALT+DEL command.

  1. In VirtualBox, go to the Input menu, select Keyboard, and then Insert Ctrl-Alt-Delete.
  2. Enter the Administrator password you just created.

Your Server 2019 Desktop will load up, giving you access to the Server Manager dashboard and the full Windows Server interface!

Ready to Build Your Network?

That was a quick, step-by-step walkthrough of installing Windows Server 2019! Whether you chose a virtual environment or a physical machine, you now have a solid foundation for building and managing your own server infrastructure.

If you found this tutorial useful and are ready to tackle the next steps in system administration, please do like this post and subscribe to Darren’s Tech Tutorials for more clear, accessible guides. If you ran into any issues, leave a comment below—I’m always happy to help!