Tools of the Trade of a Penetration Tester

Penetration Testing, a critical aspect of cybersecurity, involves a wide array of tools each specialized for different aspects of a security assessment. Understanding these tools and their functions is essential for any cybersecurity professional. This article breaks down these tools into categories based on their primary functions, providing an insight into the tools of the trade for Penetration Testers. For additional techniques on these tools, visit our cyber tools section.

1. Reconnaissance Tools

Reconnaissance, or recon, is a crucial phase in penetration testing where information about the target system is gathered. Here is a list of 10 popular reconnaissance tools used by cybersecurity professionals:

1. Nmap (Network Mapper): A powerful tool used for network discovery and security auditing. Nmap can scan large networks as well as single hosts to identify what hosts are available, services offered, operating systems running, and other valuable information.
2. Shodan: Often referred to as a search engine for the Internet of Things (IoT), Shodan can find and provide information about devices connected to the internet, including servers, webcams, and industrial control systems.
3. Maltego: An interactive data mining tool that renders directed graphs for link analysis. It’s particularly effective for gathering information about network relationships, infrastructure, and individuals.
4. TheHarvester: A tool designed for gathering email accounts, subdomain names, hosts, employee names, open ports, and banners from different public sources like search engines and PGP key servers.
5. Recon-ng: A full-featured Web Reconnaissance framework written in Python. It’s aimed at reducing the time spent on reconnaissance by automating the process with various modules.
6. Netcraft: Provides various internet security services including anti-fraud and anti-phishing services, application testing, and site reports that detail the hosting provider, country, and uptime of a website.
7. Wireshark: While primarily known as a network protocol analyzer, Wireshark can also be used in the reconnaissance phase to analyze and sniff network traffic to gather information about a target.
8. OpenVAS (Open Vulnerability Assessment System): A framework of tools that offer a comprehensive and powerful vulnerability scanning and vulnerability management solution.
9. Nikto: A web server scanner that performs comprehensive tests against web servers, including over 6700 potentially dangerous files/programs, checks for outdated versions of over 1250 servers, and version-specific problems on over 270 servers.
10. OSINT Framework: An open-source tool for information gathering, mainly through publicly available information (Open Source Intelligence or OSINT). It provides a structured way to harness a wealth of information from the public domain.

Additional – SN1PER, HUNTER.IO

2. Traffic Analysis Tools

Traffic analysis is a critical aspect of network security and penetration testing, focusing on inspecting, monitoring, and analyzing network traffic to detect anomalies, vulnerabilities, or unauthorized activity. Here’s a list of 10 tools commonly used for traffic analysis in cybersecurity:

1. Wireshark: A widely-used network protocol analyzer, allowing users to capture and interactively browse the traffic running on a computer network. It’s essential for deep packet analysis and troubleshooting network issues.
2. Tcpdump: A powerful command-line packet analyzer; it allows the user to capture and display the traffic passing through a network interface using filters to narrow down the data.
3. Snort: An open-source network intrusion detection system (NIDS) that can perform real-time traffic analysis and packet logging on IP networks for the detection of anomalies and possible threats.
4. Arkime: An open-source, large scale, full packet capturing, indexing, and database system.
5. NetworkMiner: A network forensic analysis tool (NFAT) for Windows that can detect the OS, hostname, and open ports of network hosts through packet sniffing or by parsing a PCAP file.
6. Suricata: An open-source network threat detection tool. It functions as a network IDS, intrusion prevention system (IPS), and network security monitoring (NSM) solution, using rules to inspect network traffic.
7. Zeek (previously known as Bro): An open-source network analysis framework that transforms network traffic into comprehensive logs, file content, and fully-customizable, real-time alerts.
8. Tshark: The command-line version of Wireshark, offering similar packet capturing and analysis capabilities but suitable for automation in scripts and for use on remote or headless servers.
9. Fiddler: A web debugging tool that captures HTTP and HTTPS traffic between chosen computers and the internet, allowing inspection of incoming and outgoing data to monitor and modify requests and responses before they hit the browser.
10. EtherApe: A graphical network monitor for Unix modeled after etherman, displaying network activity graphically with network traffic segmented by protocol and subdivided by source and destination.

3. Vulnerability Exploitation Tools

Vulnerability exploitation tools are designed to identify, analyze, and exploit vulnerabilities in systems and networks. They are essential for penetration testers to assess the security of systems. Here is a list of 10 notable tools used for vulnerability exploitation:

1. Metasploit: One of the most popular frameworks for developing, testing, and executing exploit code against a remote target machine. It also includes tools for network discovery and vulnerability scanning.
2. Exploit-DB: A non-commercial project that provides a comprehensive database of known exploits, making it a valuable resource for penetration testers looking for existing exploits.
3. SQLmap: An open-source penetration testing tool that automates the process of detecting and exploiting SQL injection flaws and taking over database servers.
4. John the Ripper: A fast password cracker, currently available for many flavors of Unix, Windows, DOS, BeOS, and OpenVMS. It’s used to test password strength and sometimes to recover lost passwords.
5. Hashcat: An advanced password cracking tool that is popular for its versatility and speed. It supports a wide range of hash types and algorithms.
6. Burp Suite Intruder: A part of the Burp Suite set of tools, this tool is used for automating attacks against web applications. It is useful for tasks like testing form submissions or authentication mechanisms.
7. Canvas: A commercial vulnerability exploitation tool that allows easy testing of a large number of systems for vulnerabilities. It is known for its regularly updated database of exploits.
8. Nessus: While primarily a vulnerability scanner, Nessus also contains features for exploitation such as identifying known vulnerabilities that can be exploited with Metasploit and other frameworks.
9. Core Impact: A commercial tool used by security experts to evaluate the security of a system by safely exploiting vulnerabilities. It supports a wide range of network infrastructures, operating systems, and applications.
10. Immunity Debugger: A powerful tool combining a debugger with a comprehensive vulnerability research tool. It is particularly useful for analyzing exploits and understanding their structure and impact.

4. Web Application Security Testing Tools

Web application security testing tools are specialized software designed to test web applications for security vulnerabilities. These tools play a crucial role in ensuring the security of web-based applications against various types of cyber threats. Here’s a list of 10 prominent tools used for web application security testing:

1. OWASP Zed Attack Proxy (ZAP): An open-source web application security scanner. It’s designed to automatically find security vulnerabilities in web applications during development and testing phases.
2. Burp Suite: A popular integrated platform for performing security testing of web applications. It offers a range of tools for scanning, probing, and attacking web applications.
3. Invicti (formerly Netsparker): An automated tool that scans web applications for vulnerabilities like SQL Injection and Cross-site Scripting (XSS), and provides detailed information about the vulnerabilities it discovers.
4. WebInspect: A dynamic application security testing tool by Micro Focus that identifies known and unknown vulnerabilities within the web application layer.
5. Acunetix: A comprehensive tool that scans and reports on a wide array of vulnerabilities. It’s known for its fast scanning capabilities and detailed reporting.
6. AppScan: A tool from IBM, it provides application security testing and risk management with a suite of automated security testing tools that deliver comprehensive vulnerability assessments.
7. Veracode: Offers an automated, on-demand, application security testing solution that is capable of scanning and auditing all types of web applications, including those that are complex and large.
8. Qualys Web Application Scanning (WAS): A cloud-based service that provides automated crawling and testing of custom web applications to identify vulnerabilities.
9. SQLMap: An open-source penetration testing tool that automates the process of detecting and exploiting SQL injection flaws and taking over of database servers.
10. W3af (Web Application Attack and Audit Framework): An open-source web application security scanner which helps in identifying and exploiting web application vulnerabilities.

5. Custom Scripting and Automation Tools

Custom scripting and automation tools are essential for streamlining the process of penetration testing and cybersecurity analysis. These tools allow security professionals to create bespoke solutions for specific security challenges, automate repetitive tasks, and efficiently manage data and network interactions. Here’s a list of 10 tools widely used for custom scripting and automation in cybersecurity:

1. Python: A versatile, high-level programming language that is widely used in cybersecurity for its ease of use and vast array of libraries, making it ideal for scripting and automating security tasks.
2. PowerShell: A task automation and configuration management framework from Microsoft, consisting of a command-line shell and associated scripting language. It’s widely used for automating administrative tasks and managing Windows-based systems.
3. Ruby: A dynamic, open-source programming language with a focus on simplicity and productivity, which has a range of applications in writing custom scripts for security and network analysis.
4. Bash (Bourne Again SHell): A Unix shell and command language, which is a default shell on Linux and macOS. Bash scripts are commonly used for automating tasks in penetration testing and system administration.
5. Perl: A high-level, general-purpose, interpreted, dynamic programming language known for its capabilities in text processing, which is useful in writing custom scripts for log analysis, pattern matching, and more.
6. Ansible: An open-source tool for software provisioning, configuration management, and application deployment. It enables infrastructure as code and is widely used for automating complex IT tasks.
7. Chef: A powerful automation platform that transforms infrastructure into code. Chef automates how infrastructure is configured, deployed, and managed across network devices.
8. Puppet: A configuration management tool used for deploying, configuring, and managing servers. It automates repetitive tasks, quickly deploying critical applications, and proactively managing change.
9. Terraform by HashiCorp: An open-source infrastructure as code software tool that allows building, changing, and versioning infrastructure safely and efficiently.
10. Selenium: Primarily used for automating web applications for testing purposes, but it is also effectively used in automating repetitive web-based administration tasks.

6. Wireless Network Testing Tools

Wireless network testing is essential for assessing the security of Wi-Fi networks and identifying vulnerabilities that could be exploited by attackers. Here’s a list of 10 tools commonly used for wireless network testing and security analysis:

1. Aircrack-ng: A complete suite of tools to assess Wi-Fi network security. It focuses on different areas of Wi-Fi security including monitoring, attacking, testing, and cracking.
2. Wireshark: While mainly known as a network protocol analyzer for wired networks, Wireshark can also be used to capture and analyze wireless traffic, providing insights into the security and performance of wireless networks.
3. Kismet: A wireless network and device detector, sniffer, wardriving tool, and WIDS (wireless intrusion detection) framework. Kismet works with Wi-Fi interfaces, Bluetooth interfaces, and some SDR (software-defined radio) hardware like RTLSDR.
4. AirSnort: A wireless LAN (WLAN) tool that recovers encryption keys. AirSnort operates by passively monitoring transmissions and computing encryption keys once enough packets have been gathered.
5. Netspot: A wireless survey tool for collecting, visualizing, and analyzing Wi-Fi data. It’s useful for assessing signal strength, planning Wi-Fi setups, and ensuring efficient network coverage and performance.
6. CommView for WiFi: A powerful wireless network monitor and analyzer for 802.11 a/b/g/n/ac networks. It provides a detailed picture of network traffic, helps identify network problems, and assists in site surveys.
7. WiFi Explorer: A tool that allows you to scan, monitor, and troubleshoot wireless networks. It provides useful information about network performance and helps identify channel conflicts and overlapping signals.
8. WirelessNetView: A small utility that runs in the background and monitors the activity of wireless networks around you. It displays information about each network, including the SSID, signal quality, and more.
9. Fern WiFi Wireless Cracker: A security auditing and attack software program written for Linux. It is used to discover network vulnerabilities and weaknesses in wireless networks.
10. inSSIDer: A Wi-Fi network scanner for Windows and Mac OS that displays Wi-Fi access points and clients in real-time, tracks signal strength over time, and helps optimize channel settings.

7. Password Cracking and Credential Testing Tools

Password cracking and credential testing are critical components of cybersecurity, used for assessing the strength of passwords and identifying vulnerabilities in authentication mechanisms. Here’s a list of 10 tools commonly used for password cracking and credential testing:

1. John the Ripper: An open-source password cracking tool widely used for its ability to automatically detect password hash types and perform dictionary, brute-force, and rainbow table attacks.
2. Hashcat: Known for its speed and versatility, Hashcat is a robust password recovery tool that supports many hashing algorithms, making it suitable for cracking a wide range of password types.
3. RainbowCrack: Uses time-memory tradeoff algorithm to crack hashes. It generates rainbow tables for using during the attack process, significantly speeding up the cracking of complex passwords.
4. Hydra (THC-Hydra): A fast network logon cracker that supports numerous protocols to attack, such as telnet, FTP, HTTP/S, SMB, and more. It is widely used in brute force attacks for password guessing.
5. Ophcrack: A free Windows password cracker based on rainbow tables. It is efficient in cracking most Windows passwords up to Windows 7.
6. Cain & Abel: A multipurpose tool for Microsoft Operating Systems. It can recover many kinds of passwords using methods such as network packet sniffing and employing various password cracking techniques like dictionary, brute-force, and cryptanalysis attacks.
7. CrackStation: A web-based interface for cracking password hashes. It utilizes massive pre-computed lookup tables to crack password hashes.
8. Medusa: A command-line tool for conducting parallel, speedy, and modular brute-force attacks on a variety of network services, including HTTP, SMB, FTP, and SSH.
9. Aircrack-ng: Primarily a Wi-Fi security tool, but it also includes a password cracking utility to test the strength of WPA/WPA2 passwords.
10. L0phtCrack: A password auditing and recovery tool that uses numerous methods to crack Windows passwords, including brute-force, dictionary, and hybrid attacks.

8. Social Engineering and Phishing Tools

Social engineering and phishing are tactics used to deceive individuals into divulging confidential or personal information that may be used for fraudulent purposes. Here’s a list of 10 tools commonly used for social engineering and phishing campaigns in cybersecurity:

1. Social-Engineer Toolkit (SET): An open-source tool designed to perform advanced attacks against the human element, including phishing, spear-phishing, and other social engineering tactics.
2. Gophish: An open-source phishing framework that makes it easy to create and track phishing campaigns with detailed reporting.
3. PhishX: A tool used for spear phishing and gathering information on social media platforms. It’s tailored for phishing attacks with advanced options like capturing credentials and webcam snapshots.
4. King Phisher: A tool for testing and promoting user awareness by simulating real-world phishing attacks. It supports sending phishing emails as well as hosting phishing websites.
5. BeEF (Browser Exploitation Framework): A penetration testing tool that focuses on the web browser. BeEF hooks one or more web browsers and uses them as beachheads for launching directed command modules and further attacks against the system.
6. Phishing Frenzy: An open-source Ruby on Rails application designed for managing phishing campaigns to assess the susceptibility of an organization to phishing attacks.
7. SpearPhisher: A simple point-and-click tool for creating and managing spear-phishing emails in complex security awareness testing scenarios.
8. Evilginx2: An advanced man-in-the-middle attack framework used for phishing credentials and session cookies from any web service. It’s a powerful tool for bypassing two-factor authentication (2FA).
9. Wifiphisher: A rogue Access Point framework for conducting red team engagements or Wi-Fi security testing. It can be used for various Wi-Fi-based social engineering attacks, including evil twin attacks.
10. BEEF (Browser Exploitation Framework): Primarily targeting web browsers, BEEF provides penetration testers with tools for demonstrating the impact of vulnerabilities like XSS (Cross-Site Scripting).

Custom Tool Development

Standard tools, while foundational, sometimes fall short in addressing specific security assessment scenarios. Here, custom tool development becomes pivotal. Penetration Testers with robust programming skills can tailor tools and scripts to meet the unique demands of each testing environment.

Scripting languages like Python, Ruby, and Perl are particularly favored for their flexibility and efficiency. They enable the creation of custom scripts that automate repetitive tasks, manipulate data, and handle network protocols effectively. This capability to develop bespoke tools empowers testers to uncover vulnerabilities that might elude standard testing software.

Continuous Learning and Community Engagement

The field of cybersecurity is in a constant state of flux, with new threats and technologies emerging regularly. To stay ahead, Penetration Testers must continually expand their knowledge base and toolset.

This involves engaging in beta testing of new tools, contributing to open-source security projects, and even developing proprietary software solutions that address novel security challenges.

Active participation in cybersecurity forums, social media platforms, and conferences is also a key aspect of a Penetration Tester’s professional development.

These platforms offer opportunities to exchange knowledge, discover innovative tools and techniques, and stay informed about the latest trends in cybersecurity.

By immersing themselves in the cybersecurity community and staying abreast of emerging threats and solutions, Penetration Testers can refine their skills and methodologies.

This commitment to continuous learning and community involvement ensures that they remain at the forefront of cybersecurity, equipped to provide the most effective defenses against sophisticated cyber attackers.