Basic Man-in-the-Middle

Basic Man-in-the-Middle - Traffic Interception and Manipulation

Basic Man-in-the-Middle (MitM) attacks position attackers between communicating parties to intercept, monitor, and manipulate network communications, providing capabilities for credential harvesting, session hijacking, and traffic modification.

Understanding MitM Attack Positioning

Interception Positioning: MitM attacks require strategic network positioning to place the attacker’s system in the communication path between target systems.

Active Manipulation: Unlike passive sniffing, MitM attacks actively participate in communications, enabling real-time traffic modification and injection.

Protocol Exploitation: MitM techniques exploit trust relationships in network protocols to redirect traffic through attacker-controlled systems.

MitM Attack Categories

Network-Layer Positioning:

  • ARP spoofing for Layer 2 traffic redirection (see Layer 2 Attacks module)
  • DHCP manipulation for gateway assignment
  • Route injection for network path control

Application-Layer Interception:

  • DNS spoofing for hostname resolution control
  • HTTP/HTTPS proxy interception
  • SSL/TLS downgrade and certificate manipulation

Session-Layer Exploitation:

  • Session token theft and replay
  • Cookie manipulation and injection
  • Authentication bypass through session control

Attack Methodology Overview

Positioning Phase

  • Network Analysis: Understanding target network topology and communication flows
  • Trust Relationship Identification: Mapping protocol trust dependencies
  • Optimal Positioning: Selecting attack vectors for maximum traffic interception

Interception Phase

  • Traffic Redirection: Implementing techniques to route traffic through attacker
  • Communication Monitoring: Real-time analysis of intercepted communications
  • Credential Harvesting: Extraction of authentication information from traffic

Manipulation Phase

  • Content Modification: Real-time alteration of intercepted communications
  • Session Control: Manipulation of authentication and session state
  • Attack Injection: Insertion of malicious content into legitimate sessions

Professional Context

Basic MitM attacks are fundamental to security assessment because they:

  • Test Network Segmentation: Validate effectiveness of network isolation controls
  • Assess Protocol Security: Evaluate resilience of communication protocols to interception
  • Verify Encryption Implementation: Test proper deployment of secure communication protocols
  • Demonstrate Attack Vectors: Show realistic threats to business communications

Module Structure

This module covers five essential Basic Man-in-the-Middle categories:

MitM Fundamentals

Core concepts, positioning strategies, and fundamental techniques for man-in-the-middle attack implementation.

Network-Layer Positioning

DHCP manipulation, route injection, and integration with Layer 2 ARP techniques for network-level traffic redirection.

DNS Spoofing

Domain name resolution manipulation and cache poisoning techniques for traffic redirection and phishing.

HTTP/HTTPS Interception

Web traffic interception, SSL stripping, and certificate manipulation for application-layer attack positioning.

Session Hijacking

Authentication bypass through session token theft, cookie manipulation, and session replay attacks.

Basic Man-in-the-Middle attacks demonstrate the critical importance of end-to-end encryption and certificate validation, providing essential skills for testing network security while highlighting fundamental vulnerabilities in network communication protocols.