Network Penetration Testing

This phase establishes the "rules of the game" and is critical for a safe and successful test.

1.1. Define Objectives and "Flags"

• Objectives: Clearly define the goals. Is it to gain Domain Administrator rights? Access a specific database? Steal a file from a specific server?
• "Flags": Define what constitutes success (e.g., "Capture the flag" by retrieving a proof.txt file from the Domain Controller).

1.2. Define Scope

• In-Scope Assets: Explicitly list all target IP ranges, subnets, domains, and applications.
• Out-of-Scope Assets: Define what must not be tested (e.g., production systems, third-party assets, Industrial Control Systems).
• Test Type:

1.3. Establish Rules of Engagement (ROE)

• Authorization: Obtain explicit, written permission in a signed contract or "Get Out of Jail Free" card.
• Testing Window: Define precise dates and times when testing (especially disruptive exploitation) is permitted.
• Communication Channels: Establish a dedicated 24/7 point of contact and communication channel (e.g., for reporting critical findings immediately or stopping the test if an issue arises).
• Data Handling: Define how sensitive data found during the test will be handled, stored, and ultimately purged.

2.1. Passive Reconnaissance and OSINT

• Gather information without directly interacting with the target's network.
• Examples: DNS record enumeration (e.g., dig, nslookup), identifying public IP blocks owned by the organization, finding employee names and emails from public sources (e.g., LinkedIn, social media), and searching for leaked credentials or code (e.g., GitHub).

2.2. Active Reconnaissance

• Directly interacting with the target's network to gather data.
• Host Discovery: Use nmap ping sweeps, arp-scan, and other tools to find live hosts within the in-scope IP ranges.
• Port Scanning: Perform comprehensive TCP and UDP port scans (nmap -sS -sU -p-) on live hosts to identify all open ports.
• Service Enumeration & Versioning: Fingerprint the services and their exact versions running on open ports (e.g., nmap -sV). This is critical for matching services to known exploits.
• OS Fingerprinting: Attempt to identify the operating system of the target hosts.

3.1. Vulnerability Mapping

• Correlate the enumerated services and versions with public vulnerability databases (e.g., CVE, Exploit-DB).
• Run a vulnerability scanner (e.g., Nessus, OpenVAS) in a non-intrusive mode to get a baseline, then manually verify the findings.

3.2. Attack Vector Identification

• Prioritize potential entry points based on exploitability and potential impact.
• Examples:

These are the primary methods used to gain the foothold:

4.1. Service Exploitation

• Attempt to exploit known vulnerabilities in public-facing services (e.g., RCE on a web server, using metasploit to exploit a known bug in an FTP server).

4.2. Password Attacks

• Password Spraying: Use a small list of common passwords (e.g., "Winter2025!", "Password123") against a large list of usernames (found during recon) for services like VPN, OWA, or SSH.
• Brute Forcing: Attempt to brute-force weak credentials on login portals (if not rate-limited).

4.3. Man-in-the-Middle (MITM) Attacks (if allowed)

• On an internal test, attempt to intercept and relay network traffic using tools like Responder or mitm6 to capture password hashes.

4.4. Post-Exploitation

• This phase simulates the actions an attacker takes after successfully gaining an initial foothold within a system or network. The primary objectives are to:
• Note: This sophisticated level of testing will only be executed with explicit, documented authorization.

4.4.1. Internal Reconnaissance

• Once on a compromised host, repeat the reconnaissance phase from this new internal vantage point.
• Identify high-value targets (e.g., Domain Controllers, file servers, databases) and map the internal network topology.

4.4.2. Privilege Escalatio

• Attempt to escalate privileges on the compromised machine.
• Windows: Look for weak service permissions, unquoted service paths, stored credentials, or missing patches (e.g., ms16-032).
• Linux: Look for SUID binaries, weak file permissions on /etc/shadow, sudo misconfigurations, or kernel exploits.

4.4.3. Lateral Movement

• Use the compromised host (and escalated privileges) to pivot and attack other systems on the internal network.
• Techniques include:
• The ultimate goal is often to gain Domain Administrator-level access, which constitutes a "total compromise" of the Windows environment.

4.4.4. Persistence

• Establish a "backdoor" to maintain access to the compromised system or network, simulating how an attacker would survive a reboot or credential change.
• Examples: Creating a new user account, planting a webshell, or creating a scheduled task that runs a reverse shell.

5.1. Reporting

• Executive Summary: A high-level, non-technical summary for management. It focuses on the business impact, risk, and a high-level overview of the findings.
• Technical Report: A detailed report for technical staff.
• Attack Narrative: A step-by-step walkthrough of the entire attack, from recon to post-exploitation. This is the most valuable part of the report.
• Vulnerability Details: For each vulnerability exploited (or found), provide a detailed description, evidence (screenshots, logs), and a risk rating (e.g., Critical, High, Medium, Low).
• Remediation: Provide clear, prioritized, and step-by-step instructions to fix each vulnerability. The focus should be on fixing the root cause (e.g., "implement a patch management program," not just "apply this one patch").

Remediation and Re-testing

• Present the findings to the client in a debrief meeting.
• After the client has implemented the fixes, perform a targeted re-test to validate that the vulnerabilities have been successfully remediated.