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AI Pentest Prompt Guide: Creating Effective Prompts for Security Testing

Overview

This guide provides best practices for crafting effective prompts when using AI for penetration testing and security analysis. Good prompts lead to more accurate, detailed, and actionable security assessments.

Core Prompt Engineering Principles

1. Role Assignment

Start your prompt by assigning the AI a specific security expert role:

You are an experienced penetration tester and security analyst with expertise in web application security, network security, and vulnerability assessment.

2. Clear Task Definition

Be specific about what you want the AI to analyze or accomplish:

Good: 

Analyze this web application for SQL injection vulnerabilities in the login form, focusing on input validation and parameterized queries.

Poor: 

Check this app for security issues.

3. Structured Input Using XML Tags

Use XML tags to organize different components of your prompt:

<target>
Application: E-commerce website
URL: https://example-shop.com
Technology: PHP/MySQL
</target>

<scope>
- Authentication mechanisms
- Payment processing
- User data handling
</scope>

<constraints>
- Read-only testing only
- No destructive actions
- Focus on OWASP Top 10
</constraints>

4. Chain of Thought Reasoning

Encourage step-by-step analysis by asking the AI to explain its reasoning:

Analyze the following code for security vulnerabilities. For each potential issue:
1. Identify the vulnerability type
2. Explain the potential impact
3. Provide a specific remediation recommendation
4. Rate the severity (Critical/High/Medium/Low)

Security-Specific Prompt Templates

Vulnerability Assessment Template

You are a senior security consultant performing a comprehensive security assessment.

<target_info>
Application: {{APPLICATION_NAME}}
Technology Stack: {{TECH_STACK}}
Environment: {{ENVIRONMENT}}
</target_info>

<assessment_scope>
{{SCOPE_DETAILS}}
</assessment_scope>

Please analyze the provided information and:
1. Identify potential security vulnerabilities
2. Categorize findings by OWASP Top 10 classification
3. Provide proof-of-concept examples where applicable
4. Suggest specific remediation steps
5. Prioritize findings by risk level

<constraints>
- Follow responsible disclosure principles
- Focus on defensive recommendations
- Provide actionable remediation guidance
</constraints>

Web Application Security Assessment Template

You are a web application security expert conducting a comprehensive security assessment.

<web_app_info>
Application: {{APPLICATION_NAME}}
URL: {{BASE_URL}}
Technology Stack: {{TECH_STACK}}
Authentication: {{AUTH_METHOD}}
</web_app_info>

<application_scope>
{{PAGES_AND_FUNCTIONALITY}}
</application_scope>

<analysis_focus>
{{SPECIFIC_CONCERNS}}
</analysis_focus>

Analyze the web application and provide:
1. OWASP Top 10 vulnerability assessment
2. Authentication and session management analysis
3. Input validation and output encoding review
4. Business logic flaw identification
5. Client-side security assessment
6. Detailed remediation recommendations with code examples

Mobile Application Security Assessment Template

You are a mobile security specialist analyzing mobile application security.

<mobile_app_info>
Platform: {{PLATFORM}} (iOS/Android)
Application: {{APP_NAME}}
Version: {{APP_VERSION}}
Architecture: {{ARCHITECTURE}}
</mobile_app_info>

<app_components>
Binary: {{BINARY_INFO}}
Manifest/Info.plist: {{MANIFEST_DATA}}
Network Communications: {{NETWORK_TRAFFIC}}
</app_components>

<analysis_focus>
{{SPECIFIC_CONCERNS}}
</analysis_focus>

Perform mobile security analysis focusing on:
1. Platform-specific security controls (iOS/Android)
2. Data storage security (keychain, shared preferences)
3. Network communication security (certificate pinning, encryption)
4. Authentication and authorization mechanisms
5. Runtime protection and anti-tampering measures
6. Privacy and permission model compliance
7. OWASP Mobile Top 10 assessment

API Security Assessment Template

You are an API security expert specializing in REST, GraphQL, and other API technologies.

<api_details>
API Type: {{API_TYPE}}
Base URL: {{API_BASE_URL}}
Authentication: {{AUTH_METHOD}}
Documentation: {{API_DOCS_URL}}
Technology: {{FRAMEWORK}}
</api_details>

<endpoints>
{{ENDPOINT_LIST}}
</endpoints>

<sample_requests>
{{REQUEST_EXAMPLES}}
</sample_requests>

Conduct comprehensive API security assessment covering:
1. Authentication and authorization vulnerabilities
2. Input validation and injection attacks
3. Rate limiting and DoS protection
4. Data exposure and information leakage
5. Business logic vulnerabilities
6. API versioning and deprecation security
7. CORS and cross-origin security policies
8. Provide specific test cases and curl commands for validation

Best Practices for AI Pentest Prompts

Do's

  • Be Specific: Include exact versions, configurations, and parameters
  • Provide Context: Explain the business purpose and criticality of systems
  • Set Boundaries: Clearly define what's in and out of scope
  • Request Evidence: Ask for specific examples and proof-of-concept code
  • Seek Prioritization: Request risk-based ranking of findings

Don'ts

  • Avoid Vague Requests: Don't ask for generic "security checks"
  • Don't Skip Context: Always provide relevant system information
  • Avoid Yes/No Questions: Ask for detailed analysis instead
  • Don't Ignore Compliance: Consider regulatory requirements in your prompts

Example Prompt Scenarios

Scenario 1: Generic Security Test

You are a security consultant performing a general security assessment.

<target>
Application: {{APPLICATION_NAME}}
Type: {{APPLICATION_TYPE}} (Web/Mobile/API/Desktop)
Technology Stack: {{TECH_STACK}}
Environment: {{ENVIRONMENT}}
</target>

<scope>
{{TESTING_SCOPE}}
</scope>

<constraints>
- Time limit: {{TIME_CONSTRAINT}}
- Access level: {{ACCESS_LEVEL}}
- Compliance requirements: {{COMPLIANCE}}
</constraints>

Conduct a comprehensive security evaluation covering:
1. Common vulnerability patterns for this technology stack
2. Configuration and deployment security
3. Authentication and access control mechanisms
4. Data protection and privacy considerations
5. Security monitoring and logging capabilities

Provide a prioritized list of findings with risk ratings and remediation timelines.

Scenario 2: Specific Feature Test with Documentation

You are a security expert testing a specific application feature.

<feature_details>
Feature: {{FEATURE_NAME}}
Functionality: {{FEATURE_DESCRIPTION}}
User Roles: {{USER_ROLES}}
Data Handled: {{DATA_TYPES}}
</feature_details>

<documentation>
Official Documentation: {{DOC_LINKS}}
API Specification: {{API_SPEC}}
Security Guidelines: {{SECURITY_DOCS}}
</documentation>

<test_parameters>
{{SPECIFIC_PARAMETERS}}
</test_parameters>

Focus your security analysis on:
1. Feature-specific vulnerabilities and edge cases
2. Compliance with documented security requirements
3. Proper implementation of security controls per documentation
4. Data flow security throughout the feature lifecycle
5. Integration security with other system components

Cross-reference findings with official documentation and provide specific sections that address or contradict your discoveries.

Scenario 3: Vulnerability Retest and Bug Bounty Report Validation

You are a senior security analyst validating and retesting reported vulnerabilities.

<original_report>
Vulnerability Type: {{VULN_TYPE}}
Severity: {{REPORTED_SEVERITY}}
Reporter: {{REPORTER_INFO}}
Discovery Date: {{DISCOVERY_DATE}}
</original_report>

<vulnerability_details>
{{VULNERABILITY_DESCRIPTION}}
</vulnerability_details>

<proof_of_concept>
{{POC_STEPS}}
</proof_of_concept>

<remediation_claims>
{{CLAIMED_FIXES}}
</remediation_claims>

Perform thorough validation by:
1. Reproducing the original vulnerability using provided PoC
2. Testing variations and edge cases of the reported issue
3. Validating effectiveness of implemented remediation measures
4. Assessing potential bypass techniques for the fix
5. Confirming the actual risk level and business impact
6. Documenting any residual risks or incomplete fixes

Provide a detailed retest report with:
- Vulnerability status (Confirmed/Fixed/Partially Fixed/False Positive)
- Evidence of testing performed
- Risk assessment validation
- Recommendations for additional security measures

Prompt Refinement Tips

  1. Iterate and Improve: Refine prompts based on AI responses
  2. Test Different Approaches: Try various prompt structures for complex scenarios
  3. Include Examples: Provide sample inputs/outputs when possible
  4. Validate Results: Cross-reference AI findings with established security frameworks
  5. Document Successful Prompts: Build a library of effective prompts for reuse

Conclusion

Effective AI prompting for security testing requires clear role definition, structured input, and specific task instructions. By following these guidelines and templates, you can leverage AI tools more effectively in your penetration testing and security assessment workflows while maintaining professional standards and ethical practices.