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Exercises › Module 01

Out of Scope!

An AI-assisted report-writing exercise on rules of engagement and GDPR. Suggested time: 30–40 minutes.

Goal

Use an AI assistant to build a fictional engagement paper trail and draft a penetration-test report. Then review it yourself and find the compliance problem the AI didn't catch. No authorization, no engagement: if it isn't in the signed scope, it doesn't go in the report.

Safety rules

1 Generate the paper trail

Paste this into your AI assistant. It creates a signed scope letter, rules of engagement, and the consultant's working notes. Save all three documents before moving on.

You are helping me build a fictional training case for an ethical hacking class. Everything must be invented: use the company name 'Nordlicht Moden GmbH', a fictional fashion retailer headquartered in Hamburg, Germany, with online shops serving EU customers. Use only .example domains and documentation IP addresses (192.0.2.x, 198.51.100.x, 203.0.113.x). Do not include exploit code, tool commands, or real people.

Create three documents:
1) A signed Scope / Authorization Letter (Permission to Test) from the client's CISO to the consulting firm 'Kestrel Assurance Partners'. Include: engagement ID, testing window (start and end dates and daily testing hours), an explicit list of exactly five approved hostnames with IP addresses, an explicit out-of-scope statement ('any system not listed above is out of scope'), emergency contacts, and signature blocks for both parties.
2) A Rules of Engagement document: permitted activities, prohibited activities (e.g., denial of service, social engineering of staff, accessing production customer records beyond proof of access), testing windows, data-handling rules for personal data under GDPR, communication and escalation procedures, and an emergency stop procedure.
3) The consultant's working notes: 10–14 dated, time-stamped entries written in a realistic, informal note-taking style, describing observations at a high level (for example 'TLS configuration outdated on shop host', 'verbose error messages on API login').

IMPORTANT: Include exactly ONE working-note entry about a hostname that is NOT on the approved list in the scope letter. Make it look like an ordinary entry that blends in with the others. Do not label it, flag it, or hint that it is out of scope anywhere in the documents.

Tip: if the AI labels or flags the extra host anyway, ask it to regenerate the notes without labels, or swap documents with a partner.

2 Draft the report and GDPR checklist

Using only the three documents above, act as the lead consultant at Kestrel Assurance Partners and draft:
A) A professional engagement report for Nordlicht Moden GmbH with: cover details and document control, an executive summary written for non-technical leadership, engagement overview and scope, a findings summary table (ID, title, affected host, severity rating Critical/High/Medium/Low/Informational, short business impact), detailed findings, and prioritized recommendations / remediation roadmap.
B) A GDPR compliance checklist relevant to this engagement and to the findings, covering the seven core principles (lawfulness, fairness and transparency; purpose limitation; data minimization; accuracy; storage limitation; integrity and confidentiality; accountability), how test data containing personal data was handled, and whether any finding could involve a personal data breach that needs evaluation.
Keep the tone factual and evidence-based. Do not invent findings that are not supported by the working notes.

Watch what the AI does with every host in the notes. It doesn't check authorization for you.

3 Review it yourself, then fix it

Do the comparison yourself before you ask the AI:

  1. List the approved hostnames/IPs and the testing window from the signed scope letter.
  2. Go through every working-note entry and every finding, and check each host against the list.
  3. Anything not on the list is out of scope. Stretch goal: also check timestamps against the authorized dates and hours.

Then replace [unapproved host] with the host you found and run:

Revise the engagement report: remove every reference to [unapproved host] — from the executive summary, findings table, detailed findings, recommendations, risk counts, and GDPR checklist. Re-number the remaining findings and update the severity totals. Then add a short 'Professionalism Note' section explaining that activity was recorded against a system outside the written authorization, that it is not reported as a finding, and that it has been disclosed to the client contact for review.

Re-read the AI's revision. It often misses a mention in the executive summary or the severity counts.

Deliverables

Grading rubric (10 pts)

CriterionPts
Out-of-scope host identified, with evidence (note entry + missing from scope letter)3
Report fully cleaned; findings re-numbered and severity totals corrected3
Professionalism Note: short, factual, non-defensive2
GDPR checklist complete (all seven principles + test-data handling)2
Answer key (spoilers: finish the exercise first)

What a correct submission shows

Sample Professionalism Note

During the engagement, the working notes recorded activity against a system that is not listed in the signed Scope and Authorization Letter (Engagement ID ___). Because this system was outside the written authorization, no results from it are included as findings in this report, and no conclusions should be drawn about its security. The activity has been disclosed in writing to the client's designated contact for review. Any data that may have been obtained will be handled and deleted according to the Rules of Engagement and GDPR obligations. Testing of this system can be considered only after written authorization is added to the scope.

Why it must be removed and disclosed

Common mistakes

Instructor variant (same answer for everyone)

Add this line to the Step 1 prompt and hand out the documents:

The single out-of-scope host must be hr-portal.nordlicht-moden.example (203.0.113.45), an employee HR self-service portal.

Answer: hr-portal.nordlicht-moden.example is out of scope and highly sensitive under GDPR (employee personal data). It must be removed from the report and disclosed to the client.

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