conducting-social-engineering-penetration-test▌
mukul975/Anthropic-Cybersecurity-Skills · updated May 25, 2026
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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.
| name | conducting-social-engineering-penetration-test |
| description | 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. |
| domain | cybersecurity |
| subdomain | penetration-testing |
| tags | - social-engineering - phishing - vishing - pretexting - GoPhish - SET - OSINT - security-awareness - red-team |
| version | '1.0' |
| author | mahipal |
| license | Apache-2.0 |
| atlas_techniques | - AML.T0088 - AML.T0052 |
| nist_ai_rmf | - GOVERN-6.2 - MAP-5.2 |
| nist_csf | - ID.RA-01 - ID.RA-06 - GV.OV-02 - DE.AE-07 |
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
| 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
# 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
{
"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
└── Challenged by Employee: 1 time
Risk Scoring
| Attack Vector | Success Rate | Risk Level | Priority |
|---|---|---|---|
| Phishing (credential harvest) | 15.9% | High | P1 |
| Vishing (info disclosure) | 39.1% | Critical | P1 |
| Physical tailgating | 60% | High | P2 |
| USB drop | 20% | Medium | P3 |
| Spear phishing (exec) | 40% | Critical | P1 |
Phase 6 — Reporting and Recommendations
Remediation Priorities
| Priority | Recommendation | Timeline |
|---|---|---|
| P1 | Deploy phishing-resistant MFA (FIDO2/WebAuthn) | 30 days |
| P1 | Implement targeted security awareness training | 14 days |
| P1 | Deploy email gateway with URL rewriting | 30 days |
| P2 | Strengthen physical access controls (mantraps, visitor badges) | 60 days |
| P2 | Implement security champion program per department | 30 days |
| P3 | Deploy USB device control policy | 30 days |
| P3 | Establish phishing reporting button in email client | 14 days |
Tools Reference
| Tool | Purpose |
|---|---|
| GoPhish | Phishing campaign management platform |
| Evilginx2 | MFA bypass via reverse proxy phishing |
| Social Engineer Toolkit (SET) | Social engineering attack framework |
| Maltego | OSINT and relationship mapping |
| theHarvester | Email and domain OSINT |
| King Phisher | Phishing campaign tool |
| Modlishka | Reverse proxy for credential interception |
References
- GoPhish: https://getgophish.com/
- Evilginx2: https://github.com/kgretzky/evilginx2
- Social Engineer Toolkit: https://github.com/trustedsec/social-engineer-toolkit
- Verizon DBIR: https://www.verizon.com/business/resources/reports/dbir/
- NIST SP 800-61: Computer Security Incident Handling Guide
How to use conducting-social-engineering-penetration-test on Cursor
AI-first code editor with Composer
Prerequisites
Before installing skills in Cursor, ensure your development environment meets these requirements:
- ›Cursor installed and configured on your development machine
- ›Node.js version 16.0+ with npm package manager (verify with
node --version) - ›Active project directory or workspace where you want to add conducting-social-engineering-penetration-test
Execute installation command
Execute the skills CLI command in your project's root directory to begin installation:
The skills CLI fetches conducting-social-engineering-penetration-test from GitHub repository mukul975/Anthropic-Cybersecurity-Skills and configures it for Cursor.
Select Cursor when prompted
The CLI will show a list of available agents. Use arrow keys to navigate and space to select Cursor:
Verify installation
Confirm successful installation by checking the skill directory location:
Reload or restart Cursor to activate conducting-social-engineering-penetration-test. Access the skill through slash commands (e.g., /conducting-social-engineering-penetration-test) or your agent's skill management interface.
Security & Verification Notice
We perform automated surface-level scans (Gen AI Scanner, Socket, Snyk) during installation. These checks detect common vulnerabilities but do not guarantee complete security. Always review skill source code and verify the publisher's reputation before production use.
Skills execute code in your development environment. Always verify the publisher's identity, review recent commits, and test in isolated environments before production deployment.
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Use Cases▌
Task Automation & Efficiency
Automate repetitive workflows and reduce manual effort
Example
Generate reports, summarize documents, draft communications
Save 3-5 hours per week on routine tasks
Knowledge Enhancement
Learn new skills, understand complex topics, get expert guidance
Example
Explain concepts, provide examples, suggest learning resources
Accelerate learning and skill development by 2x
Quality Improvement
Enhance output quality through reviews, suggestions, and refinements
Example
Review drafts, suggest improvements, catch errors
Improve work quality by 30-40% with less effort
Implementation Guide▌
Prerequisites
- ›Claude Desktop or compatible AI client with skill support
- ›Clear understanding of task or problem to solve
- ›Willingness to iterate and refine outputs
Time Estimate
15-45 minutes depending on use case complexity
Installation Steps
- 1.Install skill using provided installation command
- 2.Test with simple use case relevant to your work
- 3.Evaluate output quality and relevance
- 4.Iterate on prompts to improve results
- 5.Integrate into regular workflow if valuable
Common Pitfalls
- ⚠Expecting perfect results without iteration
- ⚠Not providing enough context in prompts
- ⚠Using skill for tasks outside its intended scope
- ⚠Accepting outputs without review and validation
Best Practices▌
✓ Do
- +Start with clear, specific prompts
- +Provide relevant context and constraints
- +Review and refine all outputs before using
- +Iterate to improve output quality
- +Document successful prompt patterns
✗ Don't
- −Don't use without understanding skill limitations
- −Don't skip validation of outputs
- −Don't share sensitive information in prompts
- −Don't expect skill to replace human judgment
💡 Pro Tips
- ★Be specific about desired format and style
- ★Ask for multiple options to choose from
- ★Request explanations to understand reasoning
- ★Combine AI efficiency with human expertise
When to Use This▌
✓ Use When
Use when skill capabilities match your task, clear ROI on time saved, and you can validate outputs. Best for repetitive tasks, learning, and quality improvement.
✗ Avoid When
Avoid when task requires deep expertise you can't validate, involves sensitive decisions, or when learning process is more valuable than speed of completion.
Learning Path▌
- 1Familiarize yourself with skill capabilities and limitations
- 2Start with low-risk, non-critical tasks
- 3Progress to more complex and valuable use cases
- 4Build expertise through regular use and experimentation
Discussion
Product Hunt–style comments (not star reviews)- No comments yet — start the thread.
Ratings
4.7★★★★★30 reviews- ★★★★★William Martinez· Dec 24, 2024
Solid pick for teams standardizing on skills: conducting-social-engineering-penetration-test is focused, and the summary matches what you get after install.
- ★★★★★Ganesh Mohane· Dec 12, 2024
conducting-social-engineering-penetration-test is among the better-maintained entries we tried; worth keeping pinned for repeat workflows.
- ★★★★★Arjun Brown· Dec 12, 2024
We added conducting-social-engineering-penetration-test from the explainx registry; install was straightforward and the SKILL.md answered most questions upfront.
- ★★★★★Kaira Harris· Nov 27, 2024
conducting-social-engineering-penetration-test fits our agent workflows well — practical, well scoped, and easy to wire into existing repos.
- ★★★★★Ishan Bhatia· Nov 15, 2024
conducting-social-engineering-penetration-test has been reliable in day-to-day use. Documentation quality is above average for community skills.
- ★★★★★Sakura Yang· Nov 3, 2024
Useful defaults in conducting-social-engineering-penetration-test — fewer surprises than typical one-off scripts, and it plays nicely with `npx skills` flows.
- ★★★★★Neel Sanchez· Oct 22, 2024
conducting-social-engineering-penetration-test has been reliable in day-to-day use. Documentation quality is above average for community skills.
- ★★★★★Isabella Martinez· Oct 18, 2024
conducting-social-engineering-penetration-test is among the better-maintained entries we tried; worth keeping pinned for repeat workflows.
- ★★★★★William Huang· Oct 6, 2024
Useful defaults in conducting-social-engineering-penetration-test — fewer surprises than typical one-off scripts, and it plays nicely with `npx skills` flows.
- ★★★★★Rahul Santra· Sep 5, 2024
Keeps context tight: conducting-social-engineering-penetration-test is the kind of skill you can hand to a new teammate without a long onboarding doc.
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