Installing Windows Server 2016 on Oracle VirtualBox
The following demonstrates installing Windows Server 2016 as a VM using Oracle VirtualBox. Active Directory starts with a Windows Server installation and setting up AD DS as the origin of the Windows domain.
Windows Server
Windows Server is a server-grade operating system developed by Microsoft, built to manage and support enterprise networks, applications, and services. It’s the central brain for many environments—running services like Active Directory, DNS, DHCP, Group Policy, and Hyper-V to keep operations secure and efficient.
Key Capabilities
- Hosts and manages network resources (users, devices, applications)
- Supports domain-based identity and access via Active Directory
- Powers virtual environments with Hyper-V
- Enables remote management and automation via PowerShell
- Provides built-in security features (Defender, BitLocker, JEA)
Download Windows Server 2016 (Evaluation)
For this lab, I used the official 180-day evaluation ISO of Windows Server 2016 from Microsoft’s Evaluation Center:
Oracle VirtualBox
Oracle VirtualBox is a free, open-source virtualization platform that lets you run multiple operating systems as VMs on a single machine. It’s perfect for simulating an enterprise lab—Active Directory, Group Policy, DNS, DHCP—without dedicated hardware.
Download Oracle VirtualBox
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 installing the AD DS server role to set up Active Directory.