Installing Windows Server 2016 on Oracle VirtualBox

The following demonstrates installing Windows Server 2016 as a VM using Oracle VirtualBox. Active Direcotry starts with a Windows server installation and setting up Active Directory with the AD DS server role as the origion of the Windows domain.

Windows Server

Windows Server is a server-grade operating system developed by Microsoft, built specifically to manage and support enterprise-level networks, applications, and services. Unlike regular desktop versions of Windows, Windows Server is optimized for handling infrastructure roles such as file storage, identity management, virtualization, web hosting, and network control.

It acts as the central brain of many IT environments — running services like Active Directory, DNS, DHCP, Group Policy, and Hyper-V to keep an organization's digital operations secure, scalable, and efficient.

Key Capabilities:

• Hosts and manages network resources (users, devices, and applications).
• Supports domain-based identity and access control through Active Directory.
• Powers virtual environments using Hyper-V.
• Facilitates remote management and automation via PowerShell and Windows Admin Center.
• Provides built-in security features like Windows Defender, BitLocker, and Just Enough Administration (JEA).

Whether managing a small office network or a global enterprise infrastructure, Windows Server serves as the backbone — delivering reliability, centralized control, and enterprise-grade performance.

Download Windows Server 2016 (Evaluation Edition)

For this lab, I used the official 180-day evaluation ISO of Windows Server 2016, which Microsoft provides for testing and learning purposes.

You can download it directly from Microsofts Evaluation Center:

Oracle VirtualBox

Oracle VirtualBox is a powerful, free, and open-source virtualization platform that allows you to run multiple operating systems as virtual machines (VMs) on a single physical computer. In the context of a Windows Server domain lab, VirtualBox provides an ideal environment to simulate enterprise setups — including Active Directory, Group Policy, DNS, and DHCP — without needing dedicated hardware.

It’s perfect for building isolated test environments where you can configure domain controllers, join client machines, and safely experiment with domain-level administrative tasks and policy management — all from one host machine.

Download Oracle VirtualBox

Oracle VirtualBox can be downloaded from here:

Windows Server 2016 Installation on Oracle VirtualBox Steps

1. Creating a new VM in Oracle VirtualBox

2. Allocating System Resources

• Base Memory
• Processors

In this example, I'm going to allocate 3460MB of base memory and 2 Processors.

3. Create a Virtual Hard Disk.

4. Configuration Summary

5. Adding the ISO Image to the VM

6. Starting up the VM

Windows Server 2016 Installation

1. Install Now

2. Select Language, click Next

3. Setup is starting

4. Select Operating System version

In this example, I'm going to install Windows Server 2016 Desktop Experience

5. Accept the license terms, click Next

6. Select the type of installation

7. Windows Installation Process

8. The user's password must be changed before signing in.

9. Reset Password

10. Press Ctrl, Alt, Del

11. Desktop Experience

12. Starting Server Manager

13. Server Manager

This demonstration included adding and setting up a new virtual machine in Oracle VirtualBox and installing Windows Server 2016 on the new VM. From here, I'll walk through setting up the DNS and DHCP server roles on this fresh installation, then from there installing the AD DS server role to setup Active Directory.