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Introduction:
In the high-stakes world of penetration testing and red team operations, technical skill is only half the battle. The other half is communication. A silent vulnerability is just a secret; a properly documented vulnerability is a fix waiting to happen. However, the industry standard for reporting often falls into the trap of dry, technical jargon that fails to resonate with the Chief Information Security Officer (CISO) or the engineering team tasked with remediation. A new, free course aims to bridge this gap, teaching security professionals how to transform raw technical data into compelling security narratives.
Learning Objectives:
- Objective 1: Master the structure of a professional pentest report, distinguishing between technical annexes and executive summaries.
- Objective 2: Learn to integrate technical artifacts (logs, screenshots, command outputs) seamlessly into a narrative format.
- Objective 3: Explore the automation of repetitive reporting tasks using Large Language Models (LLMs) and custom scripts to increase efficiency.
You Should Know:
- The Anatomy of a Red Team Report (Beyond the Raw Scan)
Most novice pentesters make the mistake of attaching a Nessus or OpenVAS scan output and calling it a day. Professional reporting requires context. The report must tell the story of the attack chain, not just list findings. According to the course highlighted by Tony Moukbel, the focus is on moving from a “vulnerability list” to a “security narrative.”
What this means: You need to explain the impact. Instead of saying “SMBv1 is enabled,” you explain how an attacker leveraged this to move laterally and access the Domain Controller.
Step‑by‑step guide to structuring a finding:
- Use a standardized naming convention (e.g.,
[CVSS Score] Finding Name - Affected Asset). - Affected Asset: Specify the IP, Hostname, or URL.
3. Risk Rating: Critical, High, Medium, Low, Info.
- Description: Explain what the vulnerability is in plain English.
- Proof of Concept (PoC): Provide the technical evidence. This is where your commands come in.
– Linux Example: If you exploited a misconfiguration using a tool, show the exact command.
Example: Extracting sensitive data via exposed .git folder wget -r https://target.com/.git/
– Windows Example: If you found cleartext passwords in memory, show the tool output.
PowerShell command to check for insecure service permissions
Get-WmiObject -Class Win32_Service | Where-Object { $<em>.StartName -eq "LocalSystem" -and $</em>.PathName -match "Program Files" } | Select-Object Name, StartName, PathName
6. Remediation: Provide clear, actionable steps to fix the issue.
2. Automating the Pipeline with LLMs
The course touches on using Large Language Models to automate reporting. While AI cannot perform the test for you, it excels at taking raw tool output and formatting it into the narrative structure described above.
Step‑by‑step guide to using AI for reporting:
- Export Tool Data: Run your tools (e.g., Nmap, Gobuster, SQLMap) and save the output to a text file.
- Create a Prompt Template: Do not just copy-paste raw data into an LLM. Create a structured prompt.
– Prompt Example: “Act as a senior penetration tester. I am providing you with the raw output of an Nmap scan against a client’s external perimeter. Please summarize the findings into an executive summary paragraph. Focus on open ports that pose a high risk, such as SMB and RDP, and explain the business impact of leaving these exposed.”
3. Refine and Verify: AI can hallucinate. Always cross-reference the AI-generated summary with the raw data before placing it in the final report.
3. Extracting Technical Artifacts for Linux Environments
When writing a report for a Linux system compromise, specific commands are required to prove persistence or data exfiltration. Your report should include these commands so the client can verify or replicate the finding in a safe environment.
Step‑by‑step guide to documenting Linux persistence:
- Identify the Cron Job: Check for malicious scheduled tasks.
– Command: `cat /etc/crontab` or `ls -la /etc/cron.`
– Report Output: “An unauthorized cron job was found executing a reverse shell every 5 minutes.”
2. Document SSH Keys: Check for unauthorized access via SSH keys.
– Command: `cat ~/.ssh/authorized_keys`
– Reporting Tip: Screenshot the contents, but blur the key hash for confidentiality.
3. Analyze Logs for Anomalies: Show the exact log entry that indicates the breach.
– Command: `grep “Accepted password for root” /var/log/auth.log | tail -20`
4. Extracting Technical Artifacts for Windows Environments
Windows environments often require PowerShell or Command Prompt snippets to prove a point, especially regarding Active Directory security.
Step‑by‑step guide to documenting AD misconfigurations:
- Check for Kerberoastable Accounts: If you performed a Kerberoasting attack, show how you identified the accounts.
– Command (PowerShell): `Get-ADUser -Filter {ServicePrincipalName -ne “$null”} -Properties ServicePrincipalName`
2. Check Local Admin Groups: Prove that privilege escalation was possible due to local admin rights on multiple machines.
– Command: `net localgroup administrators`
3. Check for Unconstrained Delegation: Identify high-value targets for compromise.
– Command: `Get-ADComputer -Filter {TrustedForDelegation -eq $True} -Properties TrustedForDelegation, Name`
5. API Security Testing Documentation
Modern red teams often target APIs. Reporting on API flaws requires showing the exact HTTP requests and responses.
Step‑by‑step guide to documenting an API IDOR (Insecure Direct Object Reference):
1. The Normal Request: Show the legitimate request.
- Burp Suite/HTTPie example:
GET /api/user/profile/1234 HTTP/1.1 Host: target.com Cookie: [Redacted Session]
2. The Exploit Request: Show the manipulated request.
- Curl Command: `curl -X GET https://target.com/api/user/profile/1235 -H “Cookie: [Redacted Session]”`
3. The Impact: “By incrementing the user ID parameter from 1234 to 1235, we were able to access the personal identifiable information (PII) of another user without authorization.”
What Undercode Say:
- Key Takeaway 1: Report Writing is a Hacking Skill. It is the only deliverable the client pays for. If the report is poor, the penetration test is perceived as poor, regardless of the technical depth of the attack.
- Key Takeaway 2: Automation Augments, but Doesn’t Replace, Analysis. Using LLMs to format reports saves hours of tedious work. However, the analyst must remain the subject matter expert, ensuring the AI does not misrepresent the technical risk.
Analysis: The cybersecurity industry is currently saturated with tools that find vulnerabilities but starved of professionals who can explain them. Tony Moukbel’s highlight of this course underscores a critical market need: the ability to translate technical exploits into business risk. By teaching report writing alongside automation, this curriculum ensures that red teamers remain indispensable. The shift toward “actionable security narratives” is not just a trend; it is a response to the reality that CISOs need budget approval from boards who do not understand code, but do understand risk.
Prediction:
We predict that within the next two years, “AI-Assisted Reporting” will become a standard line item in pentest proposals. Red teamers who fail to adapt and leverage AI for the administrative heavy lifting will be undercut by those who can deliver a more polished, faster, and cheaper final product. The future of hacking is not just about breaking in; it is about telling the story of how you broke in, and how to stop it from happening again.
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