StructuredFor DevelopersCybersecurity & Privacy

Penetration Testing Preparation Guide.

When commissioning or conducting a penetration test and wanting a structured, professional approach.

ChatGPT Β· Claude Β· GeminiΒ·BeginnerΒ·~218 tokens
Curated by the AIPP team
Last updated 14 May 2026 Β· v3
penetration-testing-preparation-guide.md Β· 218 words
You are a senior {{role}} brought in to help {{target_user}} complete a Penetration Testing Preparation Guide.

# Context
Original working context: Act as a security tester. Prepare a web application penetration testing scope and methodology for {{describe_the_application}}. Scope: {{in_scope_systems_out_of_scope}}. Include: (1) pre-engagement checklist (authorisation letter, rules of engagement, escalation contact), (2) testing methodology (reconnaissance, vulnerability scanning, exploitation, post-exploitation β€” what is in scope), (3) the OWASP Testing Guide checklist for web applications, (4) tools list with purpose (Burp Suite, OWASP ZAP, SQLMap, etc.), (5) report template for findings (executive summary, technical findings, recommendations).

# Goal
Produce the exact deliverable requested for this use-case. Make the output practical, specific, and ready to use.

# Constraints
- Use the user's variables exactly where relevant.
- Avoid generic filler and vague advice.
- Be specific to the stated audience, platform, market, role, industry, or situation.
- Ask only essential clarifying questions if required; otherwise make reasonable assumptions and continue.

# Output
Return the final deliverable in a clean, skimmable format with clear headings, bullets, tables, scripts, templates, or steps as appropriate.

The variables to fill in

PlaceholderWhat to put thereExample
{{describe_the_application}}Describe the applicationinsert your specific value
{{in_scope_systems_out_of_scope}}In scope systems out of scopeinsert your specific value
{{role}}Rolefreelance client onboarding strategist
{{target_user}}Target usera freelance consultant

How to customize this prompt

  1. Replace each {{double-curly}} with your real context.
  2. Adjust the constraints section to match your tone β€” formal, casual, blunt.
  3. If the engagement is recurring, change the duration line to mention milestones rather than days.
  4. Run it in your tool of choice. The output should be ready to paste with at most one small edit.

When to use

When commissioning or conducting a penetration test and wanting a structured, professional approach.

PRO TIP

Penetration tests without a signed scope agreement create legal liability β€” get explicit written permission for every system in scope before testing starts.

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