Adversary In The Middle (AitM) attacks intercept authentication credentials and hijack sessions by positioning malicious actors between users and legitimate services. These attacks capture both passwords and session tokens during legitimate login processes, enabling attackers to bypass multi-factor authentication and maintain persistent system access.

AitM attacks target enterprise email security and authentication systems by manipulating communication flows while appearing legitimate. Attackers maintain access to email addresses, personal information, and enterprise resources even after password resets, as stolen session tokens remain valid until they expire.

Attackers execute AitM attacks through a sophisticated four-stage process that enables authentication bypass and persistent system access.

• Network Positioning: Attackers exploit networking protocols to force devices to communicate through adversary-controlled systems rather than legitimate services.

• Real-Time Interception: All communication between victims and legitimate services passes through the attacker's infrastructure, enabling comprehensive monitoring and manipulation of data transmissions, including credential theft.

• Authentication Capture: During legitimate user authentication, attackers simultaneously capture both credentials and critical session tokens that maintain authenticated access to systems, a technique frequently used in phishing-as-a-service operations.

• Session Hijacking: Captured session tokens enable attackers to hijack authenticated sessions with full privileges, circumventing MFA protections entirely and maintaining persistent access to compromised accounts.

AitM attacks propagate through multiple vectors that exploit both technical vulnerabilities and human factors in enterprise environments.

• Phishing Email Integration: Attackers embed malicious phishing links in convincing emails, including QR code phishing attacks, that redirect users to proxy servers positioned between victims and legitimate authentication services.

• Compromised Wi-Fi Networks: Evil twin attacks create malicious Wi-Fi hotspots that appear legitimate but redirect all traffic through the attacker's infrastructure.

• DNS Manipulation: Advanced threat actors modify DNS records at internet service providers to redirect legitimate domain requests to attacker-controlled servers.

• Social Engineering: Attackers combine technical exploitation with social engineering tactics and impersonation to encourage users to authenticate via compromised channels.

• Supply Chain Compromise: Threat actors target service providers and infrastructure components through vendor email compromise to establish persistent interception capabilities across multiple organizations.

• Credential Harvesting: Attackers target personal information, including email addresses through sophisticated phishing campaigns that enable broader organizational access and lateral phishing attacks.

Organizations can implement multiple-layered defenses to prevent and mitigate AitM attacks effectively. These include the following steps:

• Certificate Pinning: Ensure applications only accept specific, pre-validated certificates for critical services to prevent proxy-based interception attempts.

• Network Intrusion Prevention: Deploy systems with AitM-specific detection rules and behavioral analysis capabilities to identify suspicious traffic patterns before compromise occurs.

• Authentication Monitoring: Establish comprehensive tracking of session tokens, login patterns, and geographic locations of authentication to detect account takeover attempts in real time.

• Secure Communication Protocols: Configure proper certificate validation and encrypted communication channels, including DKIM authentication, across all enterprise systems.

• Security Awareness Training: Conduct regular security training focused on recognizing phishing attempts and suspicious authentication requests that could indicate AitM attacks.

• Advanced Email Security: Deploy solutions that analyze authentication flows and detect proxy-based interception attempts, including protection against consent phishing and BEC scams, before compromise occurs.

Ready to protect your organization from AitM attacks that bypass traditional security controls? Get a demo to see how Abnormal can strengthen your authentication security.