Penetration testing, also known as pen testing, is a simulated cyber attack against a computer system, network, or web application to identify and exploit vulnerabilities. The goal of penetration testing is to assess the security posture of the system and uncover weaknesses that could be exploited by attackers.
- Reconnaissance (Information Gathering)
Description:
Information Gathering is the initial stage where the penetration tester collects as much information as possible about the target, including domain names, IP addresses, network infrastructure, employee details, and the technology stack.
There are two types of reconnaissance:
- passive (gathering information without interacting with the target);
- active (direct interaction with the target).
Usage Example:
Performing a WHOIS lookup to obtain registration details of a domain, including the registrant’s name, contact information, and the domain’s expiration date, which can help in identifying potential social engineering targets or finding out more about the organization’s infrastructure.
Tools:
- WHOIS: For obtaining domain registration information.
- Maltego: data mining tool for collecting and connecting information to visualize relationships between entities.
- theHarvester: tool for gathering emails, subdomains, hosts, employee names, open ports, and more from different public sources like search engines and PGP key servers.
Demonstration:
- Scanning and Enumeration
Description:
The phase involves actively probing the target to discover live hosts, open ports, and services running on those ports. Enumeration takes this a step further by identifying detailed information about network resources, shares, users, and services.
Usage Example:
Using Nmap to scan a target network for open ports and running services. For example, a scan might reveal that a web server is running on port 80 and an FTP server on port 21, along with the versions of the software running on those ports.
Tools:
- Nmap: powerful network scanning tool used to discover hosts and services on a computer network.
- Nessus: comprehensive vulnerability scanner that identifies security vulnerabilities in systems and applications.
- OpenVAS: open-source vulnerability scanner and management tool.
- Vulnerability Analysis
Description:
The tester analyzes the scan results to identify known vulnerabilities in the discovered services, which involves cross-referencing the versions of software with known vulnerabilities and misconfigurations.
Usage Example:
Using Metasploit to verify if a detected service vulnerability can be exploited. For instance, if an outdated version of Apache Tomcat is detected, Metasploit can be used to exploit the vulnerability to gain access to the server.
Tools:
- Metasploit: framework for developing, testing, and executing exploits against a target system.
- Burp Suite: web vulnerability scanner for identifying issues like SQL injection, cross-site scripting (XSS), and other web application vulnerabilities.
- Nexpose: vulnerability scanner that helps identify, assess, and manage security vulnerabilities.
- Exploitation
Description:
It involves attempting to exploit identified vulnerabilities to gain unauthorized access to systems, applications, or data. The goal is to demonstrate the potential impact of the vulnerabilities.
Usage Example:
Using Metasploit to exploit a buffer overflow vulnerability in a target application can allow the tester to execute arbitrary code on the target system and gain control.
Tools:
- Metasploit: provides a wide range of exploits and payloads for different vulnerabilities.
- Core Impact: penetration testing tool that offers advanced exploits and automated exploitation capabilities.
- Custom Scripts: Tailored exploits created specifically for unique vulnerabilities discovered during testing.
- Post-Exploitation
Description:
Once access is gained, the tester focuses on maintaining access, escalating privileges, and gathering further information from the compromised system, which is crucial for understanding the extent of potential damage.
Usage Example:
Using Meterpreter to create a persistent backdoor on the compromised system allows the tester to reconnect at any time, while the tester can also use Meterpreter to escalate privileges and access sensitive data.
Tools:
- Meterpreter: post-exploitation tool that provides a wide range of capabilities, including file system manipulation, process execution, and network pivoting.
- Empire: post-exploitation framework for Windows that provides PowerShell and Python agents.
- Cobalt Strike: adversary simulation tool for advanced post-exploitation and threat emulation.
- Social Engineering
Description:
It involves manipulating individuals to divulge confidential information or perform actions that compromise security by exploiting human psychology rather than technical vulnerabilities.
Usage Example:
Crafting a phishing email that appears to be from the IT department, asking users to reset their passwords on a fake but convincing website, and when users enter their credentials, the tester captures them.
Tools:
- Social-Engineer Toolkit (SET): A framework for automating social engineering attacks, including phishing and spear-phishing.
- Phishing Frameworks: Tools like Gophish for creating and managing phishing campaigns.
- Custom Scripts: Specific scripts designed for tailored social engineering attacks.
- Password Attacks
Description:
The attacks aim to obtain passwords to gain unauthorized access to systems; methods include brute force attacks, dictionary attacks, and password spraying.
Usage Example:
Using Hydra to perform a brute force attack on a web login page, try different combinations of usernames and passwords until a valid one is found.
Tools:
- Hydra: fast and flexible login cracker for various protocols.
- John the Ripper: popular password cracker that can detect weak passwords.
- Hashcat: advanced password recovery tool that supports a wide range of hashing algorithms.
- Web Application Testing
Description:
Testing web applications for common vulnerabilities such as SQL injection, cross-site scripting (XSS), and remote code execution. The focus is on identifying and exploiting weaknesses in web application logic and security controls.
Usage Example:
Using Burp Suite to intercept and manipulate HTTP requests to identify and exploit an SQL injection vulnerability in a web application’s login form.
Tools:
- Burp Suite: comprehensive tool for testing web application security.
- OWASP ZAP: open-source web application security scanner.
- SQLmap: automated tool for detecting and exploiting SQL injection vulnerabilities.
- Wireless Network Testing
Description:
Testing the security of wireless networks involves identifying weak encryption, rogue access points, and other vulnerabilities, which ensures the security of data transmitted over wireless networks.
Usage Example:
Using Aircrack-ng to capture and crack a WPA2 handshake, gaining access to the wireless network and potentially intercepting network traffic.
Tools:
- Aircrack-ng: suite of tools for assessing the security of wireless networks.
- Kismet: network detector, sniffer, and intrusion detection system for wireless networks.
- Wireshark: network protocol analyzer that can capture and analyze network traffic.
- Reporting and Documentation
Description:
Compiling detailed reports on the findings, vulnerabilities, exploitation methods, and remediation steps is essential for communicating the results to stakeholders and providing actionable recommendations to improve security.
Usage Example:
Using Dradis to document all the findings from the penetration test, including screenshots, logs, and detailed descriptions of each vulnerability, along with remediation steps.
Tools:
- Dradis: tool for collaboration and reporting in penetration tests.
- CherryTree: flexible, hierarchical note-taking and documentation, especially for individual use or smaller projects
- Faraday: integrated multi-user penetration testing environment for managing the lifecycle of penetration tests.
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