Agent Skills: Performing Adversary-in-the-Middle Phishing Detection

Detect and respond to Adversary-in-the-Middle (AiTM) phishing attacks that use reverse proxy kits like EvilProxy, Evilginx, and Tycoon 2FA to bypass MFA and steal session tokens.

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Skill Metadata

Name
performing-adversary-in-the-middle-phishing-detection
Description
Detect and respond to Adversary-in-the-Middle (AiTM) phishing attacks that use reverse proxy kits like EvilProxy, Evilginx, and Tycoon 2FA to bypass MFA and steal session tokens.

Performing Adversary-in-the-Middle Phishing Detection

Overview

Adversary-in-the-Middle (AiTM) phishing attacks use reverse-proxy infrastructure to sit between the victim and the legitimate authentication service, intercepting both credentials and session cookies in real time. This allows attackers to bypass multi-factor authentication (MFA). The most prevalent PhaaS kits in 2025 include Tycoon 2FA, Sneaky 2FA, EvilProxy, and Evilginx. Over 1 million PhaaS attacks were detected in January-February 2025 alone. These attacks have evolved from QR codes to HTML attachments and SVG files for link distribution.

When to Use

  • When conducting security assessments that involve performing adversary in the middle phishing detection
  • When following incident response procedures for related security events
  • When performing scheduled security testing or auditing activities
  • When validating security controls through hands-on testing

Prerequisites

  • Azure AD / Entra ID Conditional Access policies
  • SIEM with authentication log ingestion (Azure AD sign-in logs)
  • Web proxy with SSL inspection and URL categorization
  • Endpoint Detection and Response (EDR) solution
  • FIDO2/phishing-resistant MFA capability

Key Concepts

How AiTM Works

  1. Victim receives phishing email with link to attacker-controlled domain
  2. Attacker domain runs reverse proxy that mirrors legitimate login page
  3. Victim enters credentials on proxied page; credentials captured in transit
  4. Reverse proxy forwards credentials to real authentication service
  5. MFA challenge sent to victim; victim completes MFA on proxied page
  6. Attacker captures session cookie returned by legitimate service
  7. Attacker replays session cookie to access victim's account without MFA

Major AiTM Kits (2025)

| Kit | Type | Primary Targets | Evasion | |---|---|---|---| | Tycoon 2FA | PhaaS | Microsoft 365, Google | CAPTCHA, Cloudflare turnstile | | EvilProxy | PhaaS | Microsoft 365, Google, Okta | Random URLs, IP rotation | | Evilginx | Open-source | Any web application | Custom phishlets | | Sneaky 2FA | PhaaS | Microsoft 365 | Anti-bot checks | | NakedPages | PhaaS | Multiple | Minimal infrastructure |

Detection Indicators

  • Authentication from unusual IP not matching user profile
  • Session cookie reuse from different IP/device than authentication
  • Login page served from non-Microsoft/non-Google infrastructure
  • CDN requests to legitimate auth providers from phishing domains
  • Impossible travel between authentication and session usage

Workflow

Step 1: Deploy Phishing-Resistant MFA

  • Implement FIDO2 security keys or Windows Hello for Business for high-value accounts
  • Configure Conditional Access to require phishing-resistant MFA for admins
  • Enable certificate-based authentication where possible
  • Disable SMS and voice MFA for privileged accounts
  • AiTM cannot intercept FIDO2 because authentication is bound to origin domain

Step 2: Configure Conditional Access Policies

  • Require compliant/managed device for sensitive application access
  • Block authentication from anonymous proxies and Tor exit nodes
  • Enforce token binding to limit session cookie replay
  • Configure continuous access evaluation (CAE) for real-time token revocation
  • Implement sign-in risk policies that require re-authentication for risky sign-ins

Step 3: Build AiTM Detection Rules

  • Alert on sign-in followed by session from different IP within 10 minutes
  • Detect authentication where proxy IP does not match user's expected location
  • Monitor for impossible travel patterns in session usage
  • Alert on inbox rules created immediately after authentication (common post-compromise)
  • Detect new MFA method registration from suspicious sign-in

Step 4: Monitor Web Proxy for AiTM Infrastructure

  • Log and analyze DNS queries to newly registered domains
  • Detect connections to known PhaaS infrastructure IPs
  • Alert on authentication page backgrounds loaded from legitimate CDNs through proxy domains
  • Monitor for SSL certificates issued to domains mimicking corporate login pages
  • Block access to known EvilProxy/Evilginx infrastructure via threat intelligence

Step 5: Implement Post-Compromise Detection

  • Alert on mailbox forwarding rules created after suspicious authentication
  • Detect OAuth app consent after AiTM sign-in
  • Monitor for email sending patterns indicating BEC follow-up
  • Alert on SharePoint/OneDrive mass download after session hijack
  • Track lateral movement from compromised account

Tools & Resources

  • Microsoft Entra ID Protection: Risk-based Conditional Access
  • Azure AD Sign-in Logs: Authentication event analysis
  • Okta ThreatInsight: AiTM proxy detection at IdP level
  • Sekoia TDR: AiTM campaign tracking and intelligence
  • Evilginx (defensive): Understanding attack mechanics for detection

Validation

  • Phishing-resistant MFA blocks AiTM session capture in test scenario
  • Conditional Access denies session replay from different device/IP
  • SIEM alerts fire on simulated AiTM sign-in patterns
  • Web proxy blocks connections to known PhaaS infrastructure
  • Post-compromise rules detect inbox rule creation after suspicious auth