Cheatsheets

AI Prompts Cheatsheet for Penetration Testing

by n8n admin

🤖 AI Prompts Cheatsheet

Priya Nair — Prompt Engineering Expert

Why AI Changes the Game for Penetration Testing

Penetration testing is a critical activity that helps organizations identify vulnerabilities in their systems before malicious actors can exploit them. The integration of AI tools such as ChatGPT and Claude offers penetration testers a way to enhance their methodologies, automate mundane tasks, and even generate creative approaches to testing.

Before You Start: How to Set Context Properly

Setting context is essential when working with AI to ensure that the generated outputs are relevant and actionable. Always introduce your AI with the specific role it is to play by including details like the target environment, types of tests to conduct, and desired output format.

Core Prompts Cheatsheet

“You are a cybersecurity expert specializing in penetration testing. I want you to help me devise a penetration testing plan for an upcoming assessment on a web application that uses React and Node.js. Include the types of tests to perform, possible tools, and methodologies to follow.”

This prompt sets a clear context about the task and provides enough details for relevant outputs.

“List the top ten vulnerabilities found in web applications based on the OWASP Top Ten. For each vulnerability, provide a brief explanation and potential mitigation strategies.”

This can help with research on current vulnerabilities and aid in understanding the risks involved.

“Generate a hypothetical vulnerable application scenario that I can utilize to practice my penetration testing skills. Please include the technology stack used, possible vulnerabilities, and testing objectives.”

This promotes hands-on experience for penetration testers.

“Act as if you are a red team member. Create a step-by-step guide for exploiting an insecure deserialization vulnerability in a Java application. Include tools and scripts that would be effective in the exploitation process.”

This prompt focuses on practical offensive security techniques.

“Provide me with a checklist for a penetration test, including phases like information gathering, scanning, exploitation, and reporting. Detail the aspects to consider at each phase.”

A checklist can streamline the penetration testing process.

“Draft an executive summary of a recent penetration test report to present findings to stakeholders, focusing on high-level risks and recommended actions.”

This helps in communicating technical findings to non-technical stakeholders effectively.

Weak vs Strong Prompt Examples

❌ Weak: “Tell me about penetration testing.”
âś… Strong: “You are a penetration tester. Provide an overview of the steps involved in performing a penetration test, focusing on the methodologies and tools used at each stage.”
❌ Weak: “What tools should I use?”
âś… Strong: “List 5 penetration testing tools I should use for web application testing, and provide brief descriptions of what each tool does.”

Advanced Prompt Techniques

Utilizing advanced prompting techniques can yield better results from AI. Here are a few methods:

  • Role Prompting: Assign a specific role to the AI (e.g., “You are a penetration testing expert”). This provides context for the AI’s responses.
  • Chain-of-Thought: Encourage the AI to think through a problem step-by-step by structuring your prompts to require a process-oriented response.
  • Few-Shot Examples: Provide a couple of examples to show the AI exactly what type of response you’re expecting.
  • Output Formatting: Specify how you want the output structured—whether in bullet points, tables, or detailed paragraphs.

Claude vs ChatGPT: Which Works Better For This

Both AI tools have strengths. ChatGPT is typically better at generating more conversational and context-driven outputs, while Claude can be more efficient with structured information requests. It’s worth testing both tools with your specific prompts to see which better serves your needs.

Tips for Getting Consistent Results

Here are some tips to enhance your experience with AI tools:

  • Context Setting: Always start with a context-setting statement. This primes the AI for the answers you seek.
  • Specificity: Provide detailed, specific instructions to help the AI understand exactly what you need.
  • Iterative Refinement: Use follow-up prompts to refine and adjust the AI’s responses. Don’t hesitate to ask for clarification or additional details.

Quick Reference: All Prompts in One Place

1. “You are a cybersecurity expert specializing in penetration testing…”
2. “List the top ten vulnerabilities found in web applications…”
3. “Generate a hypothetical vulnerable application scenario…”
4. “Act as if you are a red team member…”
5. “Provide me with a checklist for a penetration test…”
6. “Draft an executive summary of a recent penetration test report…”

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