RooseveltAdvisors Customization
Before executing, check for user customizations at:
~/.claude/PAI/USER/SKILLCUSTOMIZATIONS/WebAssessment/
If this directory exists, load and apply any PREFERENCES.md, configurations, or resources found there. These override default behavior. If the directory does not exist, proceed with skill defaults.
🚨 MANDATORY: Voice Notification (REQUIRED BEFORE ANY ACTION)
You MUST send this notification BEFORE doing anything else when this skill is invoked.
Send voice notification:
curl -s -X POST http://localhost:8888/notify \ -H "Content-Type: application/json" \ -d '{"message": "Running the WORKFLOWNAME workflow in the WebAssessment skill to ACTION"}' \ > /dev/null 2>&1 &Output text notification:
Running the **WorkflowName** workflow in the **WebAssessment** skill to ACTION...
This is not optional. Execute this curl command immediately upon skill invocation.
WebAssessment Skill
Security assessment infrastructure integrating reconnaissance, threat modeling, and vulnerability testing.
Workflow Routing
| Trigger | Workflow |
|---|---|
| "understand application", "what does this app do", "map the application" | UnderstandApplication |
| "threat model", "attack scenarios", "how would I attack" | CreateThreatModel |
| "pentest", "security assessment", "test for vulnerabilities" | Pentest/MasterMethodology |
| "fuzz with ffuf", "directory fuzzing", "content discovery" | ffuf/FfufGuide |
| "OSINT", "reconnaissance", "open source intelligence" | osint/MasterGuide |
| "test web app", "Playwright", "browser automation" | webapp/TestingGuide |
| "bug bounty", "bounty programs" | bug-bounty/Programs |
| "vulnerability analysis with AI", "Gemini analysis" | VulnerabilityAnalysisGemini3 |
Skill Integration
WebAssessment coordinates with specialized skills:
| Phase | Skill | Purpose |
|---|---|---|
| Scope Definition | Recon | Corporate structure, domain enumeration |
| Target Discovery | Recon | Subdomains, endpoints, ports |
| Understanding | WebAssessment | App narrative, user flows, sensitive data |
| Threat Modeling | WebAssessment | Attack scenarios, test prioritization |
| Injection Testing | PromptInjection | LLM-specific attacks |
| Intelligence | OSINT | People, companies, social media |
Assessment Workflow
1. Corporate Structure (Recon) → Define scope and targets
2. Subdomain Enumeration (Recon) → Find all domains
3. Endpoint Discovery (Recon) → Extract JS endpoints
4. Understand Application → Build app narrative
5. Create Threat Model → Prioritize attack scenarios
6. Execute Testing → Test against identified threats
7. Report Findings → Document with PoCs
Recon Skill Tools
WebAssessment uses tools from the Recon skill:
# Corporate structure for scope
bun ~/.claude/skills/Security/Recon/Tools/CorporateStructure.ts target.com
# Subdomain enumeration
bun ~/.claude/skills/Security/Recon/Tools/SubdomainEnum.ts target.com
# Endpoint discovery from JavaScript
bun ~/.claude/skills/Security/Recon/Tools/EndpointDiscovery.ts https://target.com
# Port scanning
bun ~/.claude/skills/Security/Recon/Tools/PortScan.ts target.com
# Path discovery
bun ~/.claude/skills/Security/Recon/Tools/PathDiscovery.ts https://target.com
UnderstandApplication Output
Produces structured narrative including:
- Summary: Purpose, industry, user base, critical functions
- User Roles: Access levels and capabilities
- User Flows: Step-by-step processes with sensitive data
- Technology Stack: Frontend, backend, auth, third-party
- Attack Surface: Entry points, inputs, file uploads, websockets
CreateThreatModel Output
Generates prioritized attack plan:
- Threats: OWASP/CWE mapped with risk scores
- Attack Paths: Multi-step attack scenarios
- Test Plan: Prioritized with tool suggestions
- Effort Estimates: Quick/medium/extensive per threat
Threat Categories
| Category | Triggers On |
|---|---|
| Authentication | Auth mechanisms detected |
| Access Control | Multiple user roles |
| Injection | All web apps |
| Data Exposure | Sensitive data identified |
| File Upload | Upload functionality |
| API Security | API endpoints |
| WebSocket | WebSocket detected |
| Business Logic | All web apps |
| Payment Security | Payment flows |
6-Phase Pentest Methodology
Phase 0: Scoping & Preparation Phase 1: Reconnaissance (Recon skill) Phase 2: Mapping (content discovery) Phase 3: Vulnerability Analysis Phase 4: Exploitation Phase 5: Reporting
Key Principles
- Authorization first - Never test without explicit permission
- Understand before testing - Build app narrative first
- Threat model guides testing - Don't test blindly
- Breadth then depth - Wide recon, focused exploitation
- Document everything - Notes, screenshots, commands
Workflow Index
Core Assessment:
Workflows/UnderstandApplication.md- Application reconnaissanceWorkflows/CreateThreatModel.md- Attack scenario generation
Penetration Testing:
Workflows/pentest/MasterMethodology.md- 6-phase methodologyWorkflows/pentest/ToolInventory.md- Security tools referenceWorkflows/pentest/Reconnaissance.md- Asset discoveryWorkflows/pentest/Exploitation.md- Vulnerability testing
Web Fuzzing:
Workflows/ffuf/FfufGuide.md- FFUF fuzzing guideWorkflows/ffuf/FfufHelper.md- Automated fuzzing helper
Bug Bounty:
Workflows/bug-bounty/Programs.md- Program trackingWorkflows/bug-bounty/AutomationTool.md- Bounty automation
Web App Testing:
Workflows/webapp/TestingGuide.md- Playwright testingWorkflows/webapp/Examples.md- Testing patterns
OSINT:
Workflows/osint/MasterGuide.md- OSINT methodologyWorkflows/osint/Reconnaissance.md- Domain reconWorkflows/osint/SocialMediaIntel.md- SOCMINTWorkflows/osint/Automation.md- SpiderFoot/MaltegoWorkflows/osint/MetadataAnalysis.md- ExifTool analysis
AI-Powered:
Workflows/VulnerabilityAnalysisGemini3.md- Gemini deep analysis
Examples
Example 1: Full assessment workflow
User: "Security assessment on app.example.com"
→ Run UnderstandApplication to build narrative
→ Run CreateThreatModel to prioritize testing
→ Follow MasterMethodology with threat model guidance
→ Report findings with OWASP/CWE references
Example 2: Quick threat model
User: "How would I attack this app?"
→ Run CreateThreatModel on target
→ Get prioritized attack paths
→ Get test plan with tool suggestions
Example 3: Integrate with Recon
User: "Assessment on target.com including all subdomains"
→ CorporateStructure (Recon) → Find parent/child companies
→ SubdomainEnum (Recon) → Find all subdomains
→ EndpointDiscovery (Recon) → Extract JS endpoints
→ UnderstandApplication → Build app narrative
→ CreateThreatModel → Generate attack plan