What is Pivoting?

Pivoting is the art of using access obtained over one machine to exploit another machine deeper in the network. It is one of the most essential aspects of network penetration testing, and is one of the three main teaching points for this room.
Put simply, by using one of the techniques described in the following tasks (or others!), it becomes possible for an attacker to gain initial access to a remote network, and use it to access other machines in the network that would not otherwise be accessible:
In this diagram, there are four machines on the target network: one public facing server, with three machines which are not exposed to the internet. By accessing the public server, we can then pivot to attack the remaining three targets.

High-Level Overview

The methods we use to pivot tend to vary between the different target operating systems. Frameworks like Metasploit can make the process easier, however, for the time being, we'll be looking at more manual techniques for pivoting.
There are two main methods encompassed in this area of pentesting:
  • Tunnelling/Proxying: Creating a proxy type connection through a compromised machine in order to route all desired traffic into the targeted network. This could potentially also be tunnelled inside another protocol (e.g. SSH tunnelling), which can be useful for evading a basic Intrusion Detection System (IDS) or firewall.
  • Port Forwarding: Creating a connection between a local port and a single port on a target, via a compromised host.
A proxy is good if we want to redirect lots of different kinds of traffic into our target network -- for example, with an nmap scan, or to access multiple ports on multiple different machines.
Port Forwarding tends to be faster and more reliable, but only allows us to access a single port (or a small range) on a target device.
Which style of pivoting is more suitable will depend entirely on the layout of the network, so we'll have to start with further enumeration before we decide how to proceed. It would be sensible at this point to also start to draw up a layout of the network as you see it -- although in the case of this practice network, the layout is given in the box at the top of the screen.
As a general rule, if you have multiple possible entry-points, try to use a Linux/Unix target where possible, as these tend to be easier to pivot from. An outward facing Linux webserver is absolutely ideal.


We will use the following tools for pivoting:
  • RINETD is a simple port forwarding tool
  • SSH Tunneling can be used to create both port forwards, and proxies
  • Plink is an SSH client for Windows, allowing you to create reverse SSH connections on Windows
  • sshuttle is a nicer way to create a proxy when we have SSH access on a target
  • Chisel can do the exact same thing as with SSH portforwarding/tunneling, but doesn't require SSH access on the box


As always, enumeration is the key to success. Information is power -- the more we know about our target, the more options we have available to us. As such, our first step when attempting to pivot through a network is to get an idea of what's around us.
There are five possible ways to enumerate a network through a compromised host:
  1. 1.
    Using material found on the machine. The hosts file or ARP cache, for example.
  2. 2.
    Using pre-installed tools.
  3. 3.
    Using statically compiled tools.
  4. 4.
    Using scripting techniques.
  5. 5.
    Using local tools through a proxy.
These are written in the order of preference. Using local tools through a proxy is incredibly slow, so should only be used as a last resort. Ideally we want to take advantage of pre-installed tools on the system (Linux systems sometimes have Nmap installed by default, for example). This is an example of Living off the Land (LotL) -- a good way to minimize risk. Failing that, it's very easy to transfer a static binary, or put together a simple ping-sweep tool in Bash (which we'll cover below).

Static Binaries

Before anything else though, it's sensible to check to see if there are any pieces of useful information stored on the target. arp -a can be used to Windows or Linux to check the ARP cache of the machine -- this will show you any IP addresses of hosts that the target has interacted with recently. Equally, static mappings may be found in /etc/hosts on Linux, or C:\Windows\System32\drivers\etc\hosts on Windows. /etc/resolv.conf on Linux may also identify any local DNS servers, which may be misconfigured to allow something like a DNS zone transfer attack (which is outwith the scope of this content, but worth looking into). On Windows the easiest way to check the DNS servers for an interface is with ipconfig /all. Linux has an equivalent command as an alternative to reading the resolv.conf file: nmcli dev show.
If there are no useful tools already installed on the system, and the rudimentary scripts are not working, then it's possible to get static copies of many tools. These are versions of the tool that have been compiled in such a way as to not require any dependencies from the box. In other words, they could theoretically work on any target, assuming the correct OS and architecture. For example: statically compiled copies of Nmap for different operating systems (along with various other tools) can be found in various places on the internet. A good (if dated) resource for these can be found here:
A more up-to-date version of Nmap for Linux specifically can be found here:
Be aware that many repositories of static tools are very outdated. Tools from these repositories will likely still do the job; however, you may find that they require different syntax, or don't work in quite the way that you've come to expect.
The difference between a "static" binary and a "dynamic" binary is in the compilation. Most programs use a variety of external libraries (.so files on Linux, or .dll files on Windows) -- these are referred to as "dynamic" programs. Static programs are compiled with these libraries built into the finished executable file. When we're trying to use the binary on a target system we will nearly always need a statically compiled copy of the program, as the system may not have the dependencies installed meaning that a dynamic binary would be unable to run.
Finally, the dreaded scanning through a proxy. This should be an absolute last resort, as scanning through something like proxychains is very slow, and often limited (you cannot scan UDP ports through a TCP proxy, for example). The one exception to this rule is when using the Nmap Scripting Engine (NSE), as the scripts library does not come with the statically compiled version of the tool. As such, you can use a static copy of Nmap to sweep the network and find hosts with open ports, then use your local copy of Nmap through a proxy specifically against the found ports.

Living off the Land

Before putting this all into practice let's talk about living off the land shell techniques. Ideally a tool like Nmap will already be installed on the target; however, this is not always the case. If this happens, it's worth looking into whether you can use an installed shell to perform a sweep of the network. For example, the following Bash one-liner would perform a full ping sweep of the 192.168.1.x network:
for i in {1..255}; do (ping -c 1 192.168.1.${i} | grep "bytes from" &); done
The above command generates a full list of numbers from 1 to 255 and loops through it. For each number, it sends one ICMP ping packet to 192.168.1.x as a backgrounded job (meaning that each ping runs in parallel for speed), where i is the current number. Each response is searched for "bytes from" to see if the ping was successful. Only successful responses are shown.
The equivalent of this command in Powershell is unbearably slow, so it's better to find an alternative option where possible. It's relatively straight forward to write a simple network scanner in a language like C# (or a statically compiled scanner written in C/C++/Rust/etc), which can be compiled and used on the target. Or, use my Python Nmap implementation:
It's worth noting as well that you may encounter hosts which have firewalls blocking ICMP pings (Windows boxes frequently do this, for example). This is likely to be less of a problem when pivoting, however, as these firewalls (by default) often only apply to external traffic, meaning that anything sent through a compromised host on the network should be safe. It's worth keeping in mind, however.
If you suspect that a host is active but is blocking ICMP ping requests, you could also check some common ports using a tool like netcat.
Port scanning in bash can be done (ideally) entirely natively:
for i in {1..65535}; do (echo > /dev/tcp/$i) >/dev/null 2>&1 && echo $i is open; done
Bear in mind that this will take a very long time, however!


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