Quick take - Pivoting is a key technique in penetration testing that allows cybersecurity professionals to exploit a compromised system to gain deeper access within a target network through methods such as tunneling/proxying and port forwarding.

Fast Facts

Definition and Purpose: Pivoting is a key technique in penetration testing that allows cybersecurity professionals to exploit a compromised system for deeper access within a target network, facilitating lateral movement to internal systems.
Core Methodologies: The primary methods of pivoting include Tunneling/Proxying and Port Forwarding, each serving different purposes in redirecting traffic and accessing services within a network.
Tools for Tunneling/Proxying: Notable tools for tunneling and proxying include Proxychains, FoxyProxy, SSH Tunneling, Socat, Chisel, and sshuttle, which help in managing and redirecting traffic through compromised hosts.
Port Forwarding: This method connects a local machine’s port to a target machine’s port via the compromised host, using tools like SSH Forwarding, Plink, and Socat, and is optimal for accessing specific services.
Importance of Enumeration: Effective pivoting requires thorough enumeration to gather information about the network layout, utilizing tools like Nmap or Netcat, and strategies such as reviewing ARP cache and DNS configurations.

Understanding Pivoting in Penetration Testing

Pivoting is a fundamental technique in penetration testing, used by cybersecurity professionals to exploit a compromised system for deeper access within a target network. This method allows for lateral movement within a network, enabling access to internal systems that may not be directly reachable from an initial point of entry. Typically, initial access to a network, such as through a public-facing server, does not provide direct access to critical internal systems. Pivoting serves as a crucial bridge between initial access and more extensive network exploitation.

Core Methodologies of Pivoting

An illustrative scenario involves a network architecture with one public-facing server and three internal machines. In this example, the compromised server acts as a gateway, providing a means to access the internal network. The core methodologies involved in pivoting primarily include Tunneling/Proxying and Port Forwarding.

Tunneling/Proxying

Tunneling/Proxying creates a pathway for traffic to flow through the compromised host. Common protocols for this technique include HTTP, SSH, and various custom proxies. Noteworthy tools that facilitate tunneling and proxying include:

Proxychains: A Linux utility that redirects local traffic through a proxy.
FoxyProxy: A browser extension for managing proxy configurations.
SSH Tunneling: A method for redirecting traffic using the SSH protocol.
Socat: A versatile tool for traffic forwarding.
Chisel: A cross-platform tool for constructing HTTP tunnels.
Sshuttle: A VPN-like solution for tunneling on Unix-based systems.

Tunneling is particularly effective for redirecting multiple traffic types, conducting scans of internal subnets, and accessing various services.

Port Forwarding

Port Forwarding, on the other hand, connects a local machine’s port to a specific port on a target machine via the compromised host. This method tends to be faster and more reliable than tunneling, albeit with limitations to specific ports. Key tools for port forwarding include:

SSH Forwarding: Facilitates local or reverse traffic forwarding.
Plink: A command-line tool for SSH forwarding on Windows.
Socat: Also applicable for forwarding TCP/UDP ports.

Port forwarding is optimal for accessing single services and testing vulnerabilities on designated ports.

Importance of Enumeration

To effectively pivot, Enumeration is essential for gathering information about the network layout prior to executing pivoting techniques. Enumeration techniques may involve reviewing existing data on the compromised machine, such as ARP cache and DNS configurations. Utilizing pre-installed tools to identify accessible systems is another method. Deploying statically compiled tools like Nmap or Netcat is useful, particularly when pre-installed options are unavailable. Crafting simple scripts for tasks like ping sweeps and port checks can also be effective. Using Proxychains to redirect traffic from local tools to the internal network is another strategy.

Practical Tools and Techniques relevant to pivoting include Proxychains Setup, SSH Tunneling, Socat, and Chisel. Proxychains Setup allows tools like Nmap or Metasploit to route traffic through a compromised host. Configuration requires editing proxy settings and executing commands through Proxychains. SSH Tunneling can be utilized for both port forwarding and tunneling. Local forwarding directs traffic from a local port to a target machine’s port, while dynamic forwarding can establish a SOCKS proxy. Socat is useful for forwarding or relaying traffic, including setting up reverse shells. Chisel enables the creation of rapid HTTP-based tunnels, necessitating server setup on one machine and connection from the target machine.

Overall, mastering pivoting techniques is essential for cybersecurity professionals seeking to enhance their penetration testing capabilities and navigate complex network architectures effectively.

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