promptinjection

name

PromptInjection

description

Test LLM applications for prompt injection vulnerabilities — jailbreak attempts, system prompt extraction, context manipulation, guardrail bypass techniques, direct injection, indirect injection, multi-stage attacks, and reconnaissance. USE WHEN prompt injection, jailbreak, LLM security, AI security assessment, pentest AI application, test chatbot, guardrail bypass, direct injection, indirect injection, RAG poisoning, multi-stage attack, complete assessment, reconnaissance.

Customization

Before executing, check for user customizations at: ~/.claude/PAI/USER/SKILLCUSTOMIZATIONS/PromptInjection/

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.

2. Output text notification:

   Running the **WorkflowName** workflow in the **PromptInjection** skill to ACTION...
   

This is not optional. Execute this curl command immediately upon skill invocation.

PromptInjection Skill

🔒 AUTHORIZATION & ETHICAL USE REQUIREMENTS

⚠️ CRITICAL - READ BEFORE USE ⚠️

This skill is part of a Security Practice run by a security professional with extensive experience in offensive security testing.

Legal Requirements

AUTHORIZATION IS MANDATORY:

• ✅ ONLY test systems you own or have explicit written permission to test
• ✅ ONLY use these techniques as part of authorized penetration testing engagements
• ✅ ALWAYS document authorization before beginning any testing
• ✅ RESPECT scope boundaries defined in testing agreements
• ✅ FOLLOW responsible disclosure practices for any vulnerabilities discovered

UNAUTHORIZED TESTING IS ILLEGAL:

• ❌ NEVER test systems without explicit written permission
• ❌ NEVER exceed authorized scope boundaries
• ❌ NEVER use these techniques for malicious purposes
• ❌ NEVER disclose vulnerabilities publicly before vendor remediation
• ❌ NEVER exfiltrate real user data during testing

Ethical Framework

This skill exists for defensive security purposes:

1. Authorized penetration testing of client systems under formal engagement
2. Security assessment of your own systems and products
3. Research and education for improving AI/LLM security practices
4. Responsible disclosure of vulnerabilities to vendors for remediation

Any use of this skill constitutes acceptance of these terms and agreement to use only for authorized, ethical security testing purposes.

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When to Activate This Skill

Activate this skill when user says:

Direct Triggers

• "test for prompt injection", "prompt injection test", "prompt injection assessment"
• "LLM security testing", "AI security audit", "test chatbot security"
• "jailbreak test", "test for jailbreaking"
• "pentest AI application", "security test AI system"
• "check AI vulnerabilities", "assess AI security"

Research & Analysis

• "research prompt injection", "analyze LLM vulnerabilities"
• "study jailbreaking methods", "investigate AI attack vectors"

Engagement Work

• "client engagement for LLM security"
• "comprehensive AI security assessment"
• "vulnerability research for disclosure"

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Workflow Routing

When executing a workflow, output this notification:

Running the **WorkflowName** workflow in the **PromptInjection** skill to ACTION...

This skill provides 5 comprehensive testing workflows:

1. CompleteAssessment (Master Workflow)

File: Workflows/CompleteAssessment.md Triggers: "full assessment", "complete test", "comprehensive assessment" Description: End-to-end security assessment (12-20 hours)

• Phase 1: Authorization & scoping
• Phase 2: Reconnaissance (1-2 hours)
• Phase 3-5: Direct/indirect/multi-stage testing (6-8 hours)
• Phase 6-9: Defense analysis & reporting (4-6 hours)

Use for: Full security engagements, formal penetration tests

2. Reconnaissance

File: Workflows/Reconnaissance.md Triggers: "recon", "discover attack surface", "map application" Description: Application intelligence gathering via browser automation

• DOM extraction and analysis
• JavaScript inspection
• API endpoint enumeration
• Injection point identification

Use for: Initial assessment phase, attack surface mapping

3. DirectInjectionTesting

File: Workflows/DirectInjectionTesting.md Triggers: "test direct injection", "jailbreak testing", "basic injection" Description: Single-stage direct attacks

• Basic instruction override
• Jailbreaking & guardrail bypass
• System prompt extraction
• Token manipulation
• Obfuscation techniques

Use for: Quick vulnerability validation

4. IndirectInjectionTesting

File: Workflows/IndirectInjectionTesting.md Triggers: "test indirect injection", "RAG poisoning", "document injection" Description: Attacks via external data sources

• Document upload injection
• Web scraping attacks
• RAG system poisoning
• API response manipulation

Use for: Testing RAG systems, data processing pipelines

5. MultiStageAttacks

File: Workflows/MultiStageAttacks.md Triggers: "multi-stage attack", "sophisticated testing", "advanced attacks" Description: Complex multi-turn attack sequences

• Progressive escalation
• Context poisoning
• Trust exploitation chains

Use for: Advanced testing, sophisticated threat simulation

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Quick Start

For first assessment:

1. Read QuickStartGuide.md (30-60 minute methodology)
2. Verify written authorization
3. Run Reconnaissance workflow
4. Test top 5 attack types
5. Document findings

For comprehensive assessment:

1. Use CompleteAssessment workflow
2. Follow all 9 phases
3. Generate professional report

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Resource Library

Core Documentation:

• COMPREHENSIVE-ATTACK-TAXONOMY.md - 10 attack categories, 100+ techniques
• APPLICATION-RECONNAISSANCE-METHODOLOGY.md - 7-phase recon process
• DefenseMechanisms.md - Defense-in-depth strategies, remediation guidance
• AutomatedTestingTools.md - Promptfoo, Garak, PyRIT comparison
• QuickStartGuide.md - First assessment checklist (30-60 min)
• Reporting.md - Report structure, templates, presentation guidance

All resources are in the PromptInjection skill root directory.

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Key Principles

Authorization-First

1. Written authorization is mandatory
2. Document everything (scope, boundaries, approvals)
3. Respect boundaries - in-scope only
4. Stop if uncertain - clarify before proceeding

Methodical Testing

1. Systematic approach - follow established methodology
2. Document as you go - record all tests and results
3. Reproduce findings - ensure vulnerabilities are reliable
4. Assess impact accurately - distinguish theoretical vs practical risk

Responsible Disclosure

1. Give vendors time - 90-day disclosure timeline typical
2. Clear communication - detailed reproduction steps
3. Coordinate disclosure - work with vendor on timing
4. Protect users - no public details before patch

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Examples

Example 1: Quick test

User: "test this chatbot for prompt injection - I own it"
→ Verifies authorization
→ Runs Reconnaissance workflow
→ Tests top 5 attack types
→ Documents findings

Example 2: Full assessment

User: "comprehensive prompt injection assessment for client"
→ Loads CompleteAssessment workflow
→ 9-phase methodology (12-20 hours)
→ Professional report with remediation

Example 3: Research

User: "what are the latest jailbreaking methods?"
→ Searches COMPREHENSIVE-ATTACK-TAXONOMY.md
→ Returns categorized techniques with effectiveness ratings

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Support & Escalation

When to escalate:

• Authorization is unclear or questionable
• Ethical concerns arise
• Novel attack techniques discovered
• Critical 0-day vulnerabilities found

Contact:

• Configure in your USER settings

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🔒 REMINDER: AUTHORIZED USE ONLY 🔒

This skill contains powerful security testing techniques. Use only for:

• ✅ Systems you own
• ✅ Systems with explicit written authorization
• ✅ Ethical security research
• ✅ Defensive security purposes

Unauthorized use is illegal and unethical.

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