Have you ever wondered what happens during a successful cyberattack and how cybersecurity professionals respond? In real time, we’ll take you inside a particularly dangerous technique known as an Adversary-in-the-Middle (AiTM) attack, where a simulated cybercriminal steals a user’s token in Microsoft 365 (M365). Discover how effortlessly attackers can break into your systems and how effective security measures can shut them down in minutes.
What Is an Adversary-in-the-Middle (AiTM) Attack?
In an AiTM attack, a cybercriminal places themselves between a user and a trusted service—like M365—without the user knowing. The attacker can intercept login credentials, Multi-Factor Authentication (MFA) tokens, and session cookies, which allows them to impersonate the user. AiTM attacks are particularly dangerous because, even if MFA is enabled, attackers can steal tokens to gain unauthorized access to the user’s account.
This video perfectly illustrates how quickly and easily an AiTM attack can unfold if proper defenses aren’t in place.
The Attack Unfolds: Real-Time Identify Theft in an Unprotected Environme
The first part of our demo shows a user, Lester, receiving a seemingly authentic email from a trusted contact. The email contains a link to download project files from Microsoft 365. Unaware of any threat, Lester follows the standard steps: he opens the email, clicks the link, and enters his credentials, including completing the MFA process.
Here’s where the AiTM attacker steps in. While Lester is completing his MFA, the attacker intercepts his credentials and the authentication token issued by M365. The attacker inserts the token into their own browser, bypassing the need for credentials or MFA. Just like that, they’re logged into M365, with full access to everything Lester does—emails, files, and sensitive company data.
Why MFA Alone Isn't Enough
MFA has long been the gold standard for securing user accounts, adding an extra layer of security by requiring users to provide more than just a password. But as our scenario shows, MFA isn’t bulletproof.
The key takeaway? MFA is an essential cybersecurity component, but it’s no longer enough on its own to protect against more sophisticated attacks, like AiTM. Businesses need additional layers of security to detect and respond to these types of threats in real-time.
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Protected Environments: The Role of XDR, SOAR, and Automation in Stopping AiTM Attacks
The second part of the video shows the same attack, but in a protected environment, enhanced by Extended Detection and Response (XDR) and Security Orchestration, Automation, and Response (SOAR) capabilities. This setup uses automation and advanced monitoring to spot and stop the AiTM attack in its tracks.
In this scenario, Lester receives the same email, follows the same steps, and the attacker attempts to steal his token again. But here’s the difference: the automated system quickly recognizes that two separate IP addresses (one from Lester and one from the attacker) are attempting to access M365 at the same time, and flags the unusual activity.
Within minutes, the automation locks Lester’s account, revokes the attacker’s session, and forces a password reset—all before any sensitive data can be compromised. This response is possible because of real-time anomaly detection, which catches discrepancies that would be very difficult for humans to observe.
Why You Need Automated Threat Detection
As Lester learned, relying solely on MFA or manual security practices is no longer enough. Automated solutions like XDR and SOAR provide critical protection against attacks like AiTM by detecting threats faster and responding more effectively.
Automation doesn’t just detect an attack; it stops it. As demonstrated, automated systems can lock accounts, terminate sessions, and prevent further damage—all in the time it would take a human team to even realize there’s a problem.
Learn more: Managed Detection and Response Solutions
Learn from Lester: Protect Your Business from AiTM Attacks
AiTM attacks represent a growing risk in modern cybersecurity, especially for organizations relying on cloud services like M365. This demo highlights just how vulnerable your environment can be. But you don’t have to face these threats alone.
As a Managed Security Services Provider (MSSP), TechMD specializes in securing your business through proactive measures, 24/7 monitoring, and automated threat detection. By utilizing a defense-in-depth approach that leverages cutting-edge tools like XDR and AI-powered analytics, we ensure that suspicious activity—like an AiTM attack—is detected and stopped before any real damage is done. With TechMD, you get:
- Continuous Protection: Our Security Operations Center (SOC) monitors your environment around the clock, so threats are caught in real-time.
- Expert Support: We handle everything from initial threat detection to incident response and remediation, saving your team valuable time.
- Automation and AI: Using advanced automation, we lock compromised accounts, revoke sessions, and initiate a password reset—like in the protected demo.
- Tailored Security Solutions: We build custom security strategies that fit your specific needs, ensuring seamless integration with your existing tools and platforms.
Don’t wait for a cyberattack to expose vulnerabilities in your system. Reach out to TechMD today to learn how we can secure your environment and safeguard your future.
