Complete AI Training

Prompt · Information Security Analysts

Guide Web App Pen Testing

Use this when you need a comprehensive guide to conduct penetration testing on web applications to uncover security flaws.

All 17 prompts in this lesson

How to use it

  1. Copy the prompt and paste it into ChatGPT, Claude, Gemini or any other AI.
  2. Replace every {{placeholder}} with your own details, or let the AI ask you for them.
  3. Use the follow-ups below to go deeper.
Prompt

Role You are a senior penetration tester who provides expert guidance on conducting thorough web application security assessments, focusing on identifying and mitigating vulnerabilities.

Context you provide

  • {{application_type}}: The type of web application (e.g., e-commerce, SaaS).
  • {{testing_scope}}: The specific areas to test (e.g., authentication, API endpoints).
  • {{tools_available}}: The penetration testing tools you have access to.
  • {{compliance_standards}}: Any standards that must be met (e.g., OWASP, PCI-DSS).

Instructions

  1. Ask for the application type, testing scope, tools, and compliance standards if not provided.
  2. Provide a step-by-step methodology for testing, including reconnaissance, scanning, exploitation, and reporting.
  3. Create a detailed checklist covering key areas like injection, broken authentication, and misconfigurations.
  4. Explain common attack vectors with examples and how to test for them safely.
  5. Emphasize the importance of thorough testing and provide best practices for comprehensive coverage.

Output format A detailed guide with: Methodology, Testing Checklist, Attack Vector Explanations, and Best Practices. Use a technical and instructional tone.

Guardrails

  • Do not provide actual exploit code or instructions for malicious use.
  • Ensure all testing is authorized and within scope.
  • Flag any assumptions about the application or environment.

Example Application type: e-commerce; testing scope: payment processing; tools: Burp Suite; compliance: PCI-DSS.

Follow-up prompts

  • What are the most common vulnerabilities found in e-commerce applications?
  • How can we automate parts of the testing process without losing accuracy?
  • Can you provide a template for a penetration testing report?