How to install Server 2019 | Darren's Tech Tutorials

Installing Windows Server 2019: Your Complete Step-by-Step Guide

Welcome to Darren’s Tech Tutorials! Windows Server 2019 remains a foundational operating system for professional network environments, and getting it installed correctly is the crucial first step toward managing your infrastructure.

Whether you are spinning up a lab environment for practice or preparing a brand new physical machine, this tutorial walks you through every necessary step. We’ll be demonstrating this installation within Oracle VirtualBox, but rest assured, the process is virtually identical if you are installing directly onto physical hardware.

Let’s dive in and get your new server up and running!

Getting Started: Prerequisites and Downloads

Before we can begin the actual installation, we need the essential software. Windows Server 2019 is typically downloaded as an ISO file—a disk image that we can use as virtual installation media.

What You Need:

A Hypervisor: We are using VirtualBox, but VMware Workstation or Hyper-V are also suitable.
The Windows Server 2019 ISO: You can download an evaluation copy directly from Microsoft.

Pro Tip: For a direct download link and a text version of this tutorial, please visit our detailed resource page: https://darrenoneill.eu/?p=1521

Setting Up Your Virtual Environment (Creating the Virtual Machine)

If you are installing on a physical machine, you can skip this section and proceed directly to booting from the installation media. For everyone using VirtualBox, follow these steps to create a container for your new server:

Open VirtualBox and click New to start the VM creation wizard.
Name and Operating System: Give your VM a descriptive name (e.g., “Server 2019 Test”). Ensure the Type is set to “Microsoft Windows” and the Version is set to “Windows 2019 (64-bit).”
Memory Allocation: Allocate adequate RAM. For Server 2019, we recommend a minimum of 2048 MB (2 GB), but 4 GB is ideal for better performance.
Hard Disk: Select Create a virtual hard disk now. Use the default VDI (VirtualBox Disk Image) type. We recommend using Dynamically Allocated storage, which only uses physical space as needed.
Disk Size: Allocate a minimum of 50 GB for your virtual hard drive.

Once these settings are confirmed, click Create.

Mounting the Installation Media

Now that your virtual machine exists, we need to tell it where to find the operating system installer (your downloaded ISO file).

Access VM Settings: In the VirtualBox manager, select your newly created Server 2019 VM and click the Settings button.
Go to Storage: In the Settings menu, click on the Storage section.
Attach the ISO: Under the ‘Storage Tree,’ click on the empty Controller: IDE or Controller: SATA item (it usually has a small CD icon).
On the right-hand panel, click the small CD icon next to “Optical Drive” and select Choose a disk file… Navigate to and select the Windows Server 2019 ISO you downloaded earlier.
Click OK to save the settings.

Your virtual machine is now ready to boot from the installation media!

The Full Windows Server 2019 Installation Process

This is where the magic happens. Select your VM in VirtualBox and click the green Start button.

1. Initial Setup Screens

Language and Keyboard: Confirm your language, time and currency format, and keyboard layout. Click Next.
Click the large Install Now button.
Product Key: If you have a license key, enter it here. If you are using the evaluation copy, select I don’t have a product key to continue.

2. Selecting the Server Version

This is a critical choice. You will see several options.

Windows Server 2019 Standard/Datacenter (Evaluation/Standard Install): This is the Server Core installation—a command-line-only environment.
Windows Server 2019 Standard/Datacenter (Desktop Experience): This is the version we recommend for beginners and for this tutorial. This option includes the full graphical user interface (GUI) familiar to Windows users. Select the Desktop Experience version and click Next.

3. License and Installation Type

License Terms: Review the Microsoft license terms and check the box that says, “I accept the license terms.” Click Next.
Installation Type: You will be asked: “Which type of installation do you want?”
- Select Custom: Install Windows only (advanced). Since this is a fresh setup, this is the correct choice.

4. Drive Partitioning

Where do you want to install Windows? You should see the virtual disk space you allocated (e.g., 50 GB of unallocated space).
Select the unallocated space and click Next. Windows will automatically create the necessary partitions and begin copying files.

5. Finalizing the Installation

The installation process will now copy files, install features, and perform required reboots. This may take some time.

Wait for Reboots: Your VM will reboot several times. Do not press any keys when prompted to boot from CD/DVD, as this will restart the whole process.
Set Administrator Password: Once the installation is complete, the system will prompt you to create the Administrator password. Choose a strong, complex password that meets the server’s security requirements.
Click Finish.

You will now be taken to the familiar Server 2019 login screen, ready to log in using the password you just set!

Conclusion: Ready to Build Your Network!

Congratulations! You have successfully downloaded, configured, and installed Windows Server 2019 using our step-by-step guide. Your new server is now ready for configuration—whether you’re setting up Active Directory, configuring file shares, or running internal applications.

This operating system is the backbone of so many professional environments, and mastering its installation is the first big step in your IT journey.

What’s next? Log in and explore Server Manager! If this tutorial helped you get up and running, please hit that Like button, Subscribe to Darren’s Tech Tutorials for more clear, accessible guides, and let us know in the comments what you plan to do with your new Windows Server 2019 installation! Happy serving!