AI Prompts Cheatsheet for Penetration Testing

πŸ“± Mobile Security Tips

Sarah Chen — iOS Security Specialist

Why AI Changes the Game for Penetration Testing

Artificial Intelligence is transforming the landscape of penetration testing by providing tools that enhance the efficiency and accuracy of assessments. With AI, security analysts can automate mundane tasks, analyze vast amounts of data, and quickly generate insights that would traditionally take hours or even days.

Before You Start: How to Set Context Properly

Setting context is crucial for getting the most relevant responses from AI models. Always provide background information regarding the target environment, specific vulnerabilities of interest, or the tools at your disposal. This helps the AI generate focused and pertinent results.

Core Prompts Cheatsheet

1. Analyze the target for vulnerabilities:
Describe the target environment, including its IP, open ports, and any known issues.

Usage:
When to use: Before running scans or assessments.
Customization: Add specific details about the target.

Prompt:
Analyze the target environment at IP [TARGET_IP] and identify potential vulnerabilities.
2. Generate a report template:
Request a detailed template for your penetration testing report, including sections for executive summary, findings, and recommendations.

Usage:
When to use: At the planning stage of your pen test.
Customization: Specify the format you prefer (Markdown, PDF).

Prompt:
Generate a penetration testing report template in Markdown format.
3. Suggest the best tools for a specific vulnerability:
Ask the AI to recommend tools for specific vulnerabilities like SQL Injection or Cross-Site Scripting.

Usage:
When to use: After discovering a vulnerability.
Customization: Replace examples with your findings.

Prompt:
What are the best tools for exploiting an SQL Injection vulnerability?
4. Create a step-by-step guide for exploiting a vulnerability:
Get a detailed guide on how to exploit a known vulnerability, including payloads and methods.

Usage:
When to use: During the exploitation phase.
Customization: Mention specific tools you intend to use.

Prompt:
Provide a step-by-step guide for exploiting an XSS vulnerability using Burp Suite.
5. Forensics analysis and threat detection:
Inquire about methods for conducting forensics analysis on a compromised system.

Usage:
When to use: After a successful attack to learn more about the threat.
Customization: Specify the system type and observed behavior.

Prompt:
How can I analyze a Windows machine that has been compromised by malware?

Weak vs Strong Prompt Examples

❌ Weak: How do I do a pen test?
βœ… Strong: Provide a complete penetration testing plan for a web application, covering recon, scanning, exploitation, and reporting.

Advanced Prompt Techniques

Utilize techniques like role prompting where you ask the model to assume a specific role (e.g., “Act as an experienced penetration tester”), chain-of-thought to guide the AI through complex reasoning or steps, and few-shot examples to showcase what you’re looking for. Emphasizing output formatting (like specifying JSON or Markdown) is also beneficial in reducing post-processing time.

Claude vs ChatGPT: Which Works Better For This

While both Claude and ChatGPT are capable, ChatGPT often excels with context-rich prompts, providing detailed explanations and nuanced insights. Claude, conversely, may offer faster but sometimes more generalized advice. Test both with your most common scenarios to see which performs better for your use case.

Tips for Getting Consistent Results

  • Set clear context and background information in your prompts.
  • Iteratively refine your prompts based on previous outputs; if something doesn’t work, tweak the wording or specificity.
  • Regularly review AI responses to adjust your strategies and remain aligned with technological advances in security.

Quick Reference: All Prompts in One Place

  • Analyze the target environment
  • Generate a report template
  • Suggest tools for vulnerabilities
  • Step-by-step vulnerability exploitation guide
  • Forensics analysis methods