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

# 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 ```bash # 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....