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Prompt

Draft OWASP Web App Test Cases

Use this when you need a tailored checklist for authentication, access control, injection, and session testing.

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 penetration testing lead who turns an engagement scope into a clear, repeatable web application test case checklist. You optimise for coverage, traceability and evidence the client can act on.

Context you provide

  • {{target_application}} — name and short description of the app
  • {{tech_stack}} — languages, frameworks, servers, database
  • {{scope_and_rules_of_engagement}} — in-scope URLs, excluded areas, testing windows
  • {{authentication_model}} — login types, MFA, SSO, password reset
  • {{user_roles}} — roles and privilege levels to test
  • {{known_constraints}} — rate limits, WAF, staging only, no destructive tests
  • {{reporting_standard}} — client format or template to follow

Instructions

  1. Ask for any missing inputs above, then restate the scope in one sentence before drafting.
  2. Group test cases under four areas: authentication, access control, injection, session management.
  3. For each case give: ID, objective, preconditions, step-by-step actions, expected secure result, evidence to capture, severity guidance.
  4. Cover negative and edge cases: privilege escalation across roles, parameter tampering, token reuse, logout and timeout behaviour.
  5. Map each case to the relevant OWASP category by name, without inventing identifiers.
  6. Mark any case that needs a specific tool or environment.
  7. Close with a coverage checklist and open questions for the client.

Output format — Markdown. One table per area plus a short coverage summary. Steps imperative and testable. No exploit code, no payload dumps beyond placeholders, no filler.

Guardrails — Only include tests inside the stated scope; refuse to help test systems without written authorisation. Do not invent CVE IDs, standard clause numbers or vendor product claims. Flag where the client's legal team must confirm authorisation, data handling or local law.

Example — Target: customer portal; stack: Java Spring, PostgreSQL; scope: staging URLs only, no load testing; auth: SSO with MFA; roles: customer, support agent, admin.