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Prompt course · 8 lessons · 24 prompts · 1 hour · Beginner

AI for Penetration Testers

Eight short lessons take you from scoping to retesting with prompts you can use on live engagements. Each one targets a real task, like scan triage, exploit planning, and client reporting.

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What you'll learn

  • Scope To Plan: Turn a client scope document into a testing plan and rules of engagement.
  • Triage Scan Output: Sort scan results so you know which targets deserve attention first.
  • Web App Test Cases: Build clear test cases from how an application responds.
  • Plan Safe Exploits: Work through exploitation steps and debug failures with a second set of eyes.
  • Phishing Simulation Copy: Draft authorized simulation emails and read the response results.
  • Logs And Evidence: Correlate log entries and organize evidence for your findings.
  • Client-Ready Reports: Turn technical findings into executive summaries and clear explanations.
  • Fixes And Retests: Recommend fixes, plan retests, and track remediation with clients.

What's inside

8 lessons · 24 prompts
  1. Before you start · framework course RACE Prompt Framework: Role, Action, Context, ExpectationRACE fits penetration testing because it defines your role, action, context, and expected quality when documenting a SQL injection finding.
  2. Start here Owen's Thursday, two waysA day in the life of a Penetration Tester, before and after these prompts.
  3. 01 Lesson 1 · 3 prompts Scoping And Planning
  4. 02 Lesson 2 · 3 prompts Recon And Scan Triage
  5. 03 Lesson 3 · 3 prompts Web Application Testing
  6. 04 Lesson 4 · 3 prompts Exploit Planning And Troubleshooting
  7. 05 Lesson 5 · 3 prompts Phishing Simulation Support
  8. 06 Lesson 6 · 3 prompts Log And Evidence Analysis
  9. 07 Lesson 7 · 3 prompts Client Reporting And Communication
  10. 08 Lesson 8 · 3 prompts Remediation And Retesting

About this course

7 topics

Prompts for Penetration Testers, Lesson by Lesson

This course is a set of prompts built for penetration testing work. Each lesson covers one task, from scoping and planning through reporting and retesting.

You do not need to learn a new tool. You open ChatGPT, Claude, or Gemini, paste the prompt, add your details, and work with what comes back.

  1. The lessons
    1. Scoping And Planning: Use AI to turn client requirements and scope documents into a clear penetration testing plan and rules of engagement.
    2. Recon And Scan Triage: Use AI to make sense of scan outputs, prioritize targets, and prepare focused reconnaissance tasks.
    3. Web Application Testing: Use AI to plan web app tests, interpret responses, and build clear test cases from app behavior.
    4. Exploit Planning And Troubleshooting: Use AI to plan exploitation steps, debug failures, and produce safe proof-of-concept guidance.
    5. Phishing Simulation Support: Use AI to write authorized phishing simulation content and analyze employee response results.
    6. Log And Evidence Analysis: Use AI to review logs, correlate activity, and organize evidence for findings.
    7. Client Reporting And Communication: Use AI to turn technical findings into clear executive summaries, client explanations, and report sections.
    8. Remediation And Retesting: Use AI to recommend fixes, plan retests, and track remediation progress with clients.
  2. What the course covers

    Eight lessons follow the shape of a real engagement: scoping and planning, recon and scan triage, web application testing, exploit planning and troubleshooting, phishing simulation support, log and evidence analysis, client reporting and communication, and remediation and retesting.

    Each lesson gives you prompts, examples, and a short explanation of when to use them.

  3. How the lessons connect

    The lessons are in the order you usually work. You scope first, then recon, then test, then report, then retest. Each lesson builds on the notes and findings from the one before.

    If you only have time for one, start with Scoping And Planning. It sets up everything that follows.

  4. How to use the prompts well

    Give the AI your real context: the client's industry, the scope, the technology, and what you already know. The more specific you are, the more useful the answer.

    Always check the output. AI can miss a detail or suggest a step that does not fit your rules of engagement. You are still the tester.

  5. Who this course is for

    This is for working penetration testers, from early career to senior. It also fits testers who write their own reports and want to move through them faster.

    If you are new to AI tools, the lessons start simple. If you already use them, you will find prompts tuned to testing work.

  6. Safety and privacy on the job

    Client data deserves care. Use tools your firm or client approves, strip out names and personal details where you can, and follow your rules of engagement every time.

    The course shows how to keep sensitive findings out of your prompts while still getting useful help with structure and wording.

  7. Your next step

    Open the first lesson and try it on your current engagement. Pick one task, run the prompt, and see what changes in your day.

    Then work through the rest at your own pace, and keep the prompts that earn their place in your workflow.