🔒Network Security and Forensics Unit 8 – Penetration Testing & Ethical Hacking

What's This Unit About?

• Penetration testing involves authorized simulated cyberattacks on computer systems to evaluate their security
• Ethical hacking uses the same techniques as malicious hackers but with permission and for the purpose of improving an organization's defenses
• Covers the entire process from planning and reconnaissance to exploitation and reporting
• Emphasizes the importance of staying within legal and ethical boundaries while conducting these activities
• Aims to identify vulnerabilities, misconfigurations, and weaknesses in an organization's network, systems, and applications
  • Includes testing for common issues like unpatched software, weak passwords, and insecure protocols
• Provides valuable insights to help organizations prioritize and address security risks before they can be exploited by real attackers
• Requires a diverse skill set spanning technical expertise, problem-solving, and communication

Key Concepts and Terminology

• Vulnerability: A weakness or flaw in a system that can be exploited by an attacker
• Exploit: A piece of software, chunk of data, or sequence of commands that takes advantage of a vulnerability to cause unintended behavior
• Payload: The part of an exploit that performs the intended malicious action (e.g., spawning a shell, installing malware)
• Pivot: Using a compromised system as a launching point to attack other systems on the network
• Black box testing: Penetration testing with no prior knowledge of the target system's internals
• White box testing: Penetration testing with full knowledge of the target system, often with access to source code and documentation
  • Also known as glass box or clear box testing
• Gray box testing: A hybrid approach between black box and white box testing, with limited knowledge of the target system
• Lateral movement: Techniques used by an attacker to move through a network after gaining initial access

Tools of the Trade

• Kali Linux: A popular penetration testing distribution that comes pre-installed with a wide range of security tools
• Metasploit: An open-source framework for developing, testing, and executing exploit code
  • Includes a large database of known exploits and payloads
• Nmap: A powerful network scanning and discovery tool used for mapping out target networks and identifying live hosts, open ports, and running services
• Burp Suite: An integrated platform for performing web application security testing, including tools for intercepting and modifying HTTP traffic, scanning for vulnerabilities, and exploiting them
• Wireshark: A network protocol analyzer that allows capturing and inspecting network traffic at a granular level
• John the Ripper: A fast and versatile password cracking tool that supports various attack modes and password hash formats
• Hydra: A parallelized login cracker that can perform rapid dictionary attacks against a wide range of network services
• Social engineering toolkit (SET): A tool for creating customized phishing emails and malicious websites used in social engineering attacks

Planning and Reconnaissance

• Defining the scope and objectives of the penetration test, including the systems to be tested and the types of attacks to be simulated
• Gathering information about the target organization and its network through publicly available sources (e.g., company website, social media, DNS records)
  • This process is known as open-source intelligence (OSINT) gathering
• Identifying the target network's IP address ranges, domain names, and other external-facing assets
• Scanning for live hosts, open ports, and running services using tools like Nmap
  • This helps create a map of the target network and identify potential entry points
• Enumerating user accounts, network shares, and web applications to gain a more detailed understanding of the target environment
• Analyzing the collected information to prioritize targets and plan the next steps of the penetration test
• Documenting all findings and observations throughout the reconnaissance phase

Vulnerability Assessment

• Identifying and prioritizing vulnerabilities in the target systems based on the information gathered during reconnaissance
• Scanning for known vulnerabilities using automated tools like Nessus, OpenVAS, or Qualys
  • These tools compare the target systems against databases of known vulnerabilities and misconfigurations
• Manually reviewing the configuration and hardening of operating systems, applications, and network devices
• Analyzing web applications for common vulnerabilities like SQL injection, cross-site scripting (XSS), and insecure file uploads
• Testing the strength of user passwords and authentication mechanisms
• Identifying weak or outdated cryptography used in network protocols and applications
• Evaluating the effectiveness of security controls like firewalls, intrusion detection/prevention systems (IDS/IPS), and antivirus software
• Documenting all discovered vulnerabilities, along with their severity and potential impact, to be used in the exploitation phase

Exploitation Techniques

• Attempting to exploit the vulnerabilities identified during the assessment phase to gain unauthorized access or elevate privileges
• Using known exploit code from databases like Exploit-DB or Metasploit to target unpatched software vulnerabilities
• Crafting custom exploits for newly discovered or complex vulnerabilities
• Performing brute-force and dictionary attacks to crack weak passwords and gain access to user accounts
• Exploiting misconfigurations in network services (e.g., anonymous FTP access, insecure NFS shares) to access sensitive data or pivot to other systems
• Launching social engineering attacks like phishing emails or physical tailgating to trick users into revealing their credentials or granting access
• Exploiting web application vulnerabilities to steal user data, manipulate application logic, or gain control over the underlying server
• Establishing persistence on compromised systems by creating backdoor accounts, installing rootkits, or adding scheduled tasks
• Escalating privileges on compromised systems to gain administrative access and move laterally through the network

Post-Exploitation and Reporting

• Gathering evidence and documenting the successful exploitation of vulnerabilities
  • This includes capturing screenshots, network traffic, and system logs
• Analyzing the compromised systems to identify sensitive data, confidential information, or intellectual property that could be at risk
• Assessing the potential impact of the discovered vulnerabilities and successful exploits on the organization's business operations and reputation
• Generating a detailed report of the penetration test findings, including:
  • A summary of the scope, objectives, and methodology of the test
  • A list of all discovered vulnerabilities, ranked by severity and risk level
  • Descriptions of successful exploits and their potential impact
  • Recommendations for remediating the identified vulnerabilities and improving the organization's overall security posture
• Presenting the report to the organization's management and technical teams
  • This often involves a meeting to discuss the findings, answer questions, and provide guidance on prioritizing and implementing the recommended security improvements
• Providing ongoing support and follow-up to ensure that the identified issues are properly addressed and the organization's security posture is continuously improved

Ethical Considerations and Legal Framework

• Obtaining explicit written permission from the organization before conducting any penetration testing activities
  • This permission should clearly define the scope, timeline, and rules of engagement for the test
• Adhering to all applicable laws and regulations, such as the Computer Fraud and Abuse Act (CFAA) in the United States
• Following industry standards and best practices for penetration testing, such as the Penetration Testing Execution Standard (PTES) or the NIST SP 800-115
• Maintaining the confidentiality of the organization's data and systems throughout the penetration test and after its completion
• Avoiding any unnecessary disruption or damage to the organization's production systems and networks
• Properly securing and disposing of any sensitive data or artifacts obtained during the penetration test
• Providing the organization with a clear process for reporting any suspected illegal activities or policy violations uncovered during the test
• Maintaining professional liability insurance to protect against potential legal claims or damages resulting from the penetration testing activities