conducting-social-engineering-penetration-test
Design and execute a social engineering penetration test including phishing, vishing, smishing, and physical pretexting campaigns to measure human security resilience and identify training gaps.
What this skill does
# 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 ```bash # 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 | Group | Count | Pretext | Attack Vector | |-------|-------|---------|--------------| | Finance | 15 | Invoice approval | Phishing (credential harvest) | | IT Help Desk | 8 | Password reset | Vishing | | Executives | 5 | Board meeting update | Spear phishing | | New Hires (< 90 days) | 12 | HR onboarding form | Phishing (payload) | | All Employees | 200 | IT security update | Broad phishing | ## Phase 2 — Phishing Campaign ### Infrastructure Setup ```bash # 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: [email protected] # 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 ```json { "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 <[email protected]>" }, "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 <[email protected]> Dear {FirstName}, Our security team has detected unauthorized access attempts on our systems. As a precautionary measure, all employees must reset their passwords immediately. Please click below to reset your password within the next 24 hours: [Reset Password Now] -> {phishing_url} Failure to comply may result in temporary account suspension. Thank you, IT Security Team ``` **Template 2 — Finance Invoice:** ``` Subject: Invoice #INV-2025-4821 - Approval Required From: Accounts Payable <[email protected]> Hi {FirstName}, Please review and approve the attached invoice from our vendor. Amount: $47,250.00 | Due: March 15, 2025 [View Invoice] -> {phishing_url} Best regards, Accounts Payable ``` ## Phase 3 — Vishing Campaign ### Call Script Template ``` Pretext: IT Help Desk calling about suspicious login Caller: "Hi, this is [Name] from the IT Help Desk. Am I speaking with [Target Name]?" [Wait for confirmation] Caller: "We've detected some unusual login activity on your account from an unrecognized location. For your protection, I need to verify your identity before we can investigate further." Caller: "Can you confirm your employee ID and the email address associated with your account?" [Record responses] Caller: "Thank you. I'm going to send you a verification link to confirm it's really you. Can you click on it and enter your credentials so we can secure your account?" [Send phishing link via email/SMS during call] Caller: "Great, I can see you've been verified. Your account is now secured. If you notice any further issues, please call the help desk at [real number]." ``` ### Vishing Metrics to Track | Metric | Description | |--------|-------------| | Call answered | Target picked up the phone | | Engaged | Target continued conversation past initial question | | Information disclosed | Target provided credentials, employee ID, or PII | | Link clicked | Target clicked the verification link | | Credentials entered | Target entered credentials on phishing page | | Reported | Target reported the call to security | ## Phase 4 — Physical Social Engineering ### Physical Pretexting Scenarios ``` Scenario 1: Delivery Person - Arrive with package labeled for executive - Request access to deliver personally - Attempt to tailgate through secure doors - Drop USB drives in common areas Scenario 2: IT Vendor - Arrive with vendor badge (printed) - Claim scheduled maintenance on network closet - Attempt to access server rooms - Install rogue wireless AP if access gained Scenario 3: New Employee - Arrive claiming first day orientation - Request temporary badge - Attempt to access restricted areas - Photograph sensitive screens/documents Evidence Collection: - Body camera (if legally permitted and authorized) - Photographs of accessed areas - WiFi probe from rogue AP - Notes on which doors/checkpoints bypassed ``` ## Phase 5 — Metrics and Analysis ### Campaign Results Dashboard ``` Phishing Campaign Results: ├── Emails Sent: 200 ├── Emails Delivered: 195 (97.5%) ├── Emails Opened: 142 (72.8%) ├── Links Clicked: 68 (34.9%) ├── Credentials Submitted: 31 (15.9%) ├── MFA Bypassed: 8 (4.1%) [Evilginx] ├── Reported to SOC: 12 (6.2%) └── No Action: 53 (27.2%) Vishing Campaign Results: ├── Calls Made: 23 ├── Calls Answered: 18 (78.3%) ├── Engaged in Conversation: 15 (65.2%) ├── Information Disclosed: 9 (39.1%) ├── Credentials Provided: 4 (17.4%) └── Reported to Security: 2 (8.7%) Physical Assessment: ├── Tailgating Successful: 3/5 attempts ├── USB Drives Plugged In: 2/10 dropped ├── Restricted Areas Accessed: 2/4 attempted └──
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