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December 31, 2024

Defending AITM Phishing and Mamba Attacks

Analyze the challenges posed by AITM phishing threats and Mamba 2FA, and discover how to safeguard your systems effectively.
Inside the SOC
Darktrace cyber analysts are world-class experts in threat intelligence, threat hunting and incident response, and provide 24/7 SOC support to thousands of Darktrace customers around the globe. Inside the SOC is exclusively authored by these experts, providing analysis of cyber incidents and threat trends, based on real-world experience in the field.
Written by
Patrick Anjos
Senior Cyber Analyst
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31
Dec 2024

What are Adversary-in-the-Middle (AiTM) phishing kits?

Phishing-as-a-Service (PhaaS) platforms have significantly lowered the barriers to entry for cybercriminals, enabling a new wave of sophisticated phishing attacks. Among the most concerning developments in this landscape is the emergence of Adversary-in-the-Middle (AiTM) phishing kits, which enhance traditional phishing tactics by allowing attackers to intercept and manipulate communications in real-time. The PhaaS marketplace offers a wide variety of innovative capabilities, with basic services starting around USD 120 and more advanced services costing around USD 250 monthly [1].

These AiTM kits are designed to create convincing decoy pages that mimic legitimate login interfaces, often pre-filling user information to increase credibility. By acting as a man-in-the-middle, attackers can harvest sensitive data such as usernames, passwords, and even multi-factor authentication (MFA) tokens without raising immediate suspicion. This capability not only makes AiTM attacks more effective but also poses a significant challenge for cybersecurity defenses [2].

Mamba 2FA is one such example of a PhaaS strain with AiTM capabilities that has emerged as a significant threat to users of Microsoft 365 and other enterprise systems. Discovered in May 2024, Mamba 2FA employs advanced AiTM tactics to bypass MFA, making it particularly dangerous for organizations relying on these security measures.

What is Mamba 2FA?

Phishing Mechanism

Mamba 2FA employs highly convincing phishing pages that closely mimic legitimate Microsoft services like OneDrive and SharePoint. These phishing URLs are crafted with a specific structure, incorporating Base64-encoded parameters. This technique allows attackers to tailor the phishing experience to the targeted organization, making the deception more effective. If an invalid parameter is detected, users are redirected to a benign error page, which helps evade automated detection systems [5].

Figure 1: Phishing page mimicking the Microsoft OneDrive service.

Real-Time Communication

A standout feature of Mamba 2FA is its use of the Socket.IO JavaScript library. This library facilitates real-time communication between the phishing page and the attackers' backend servers. As users input sensitive information, such as usernames, passwords, and MFA tokens on the phishing site, this data is immediately relayed to the attackers, enabling swift unauthorized access [5].

Multi-Factor Authentication Bypass

Mamba 2FA specifically targets MFA methods that are not resistant to phishing, such as one-time passwords (OTPs) and push notifications. When a user enters their MFA token, it is captured in real-time by the attackers, who can then use it to access the victim's account immediately. This capability significantly undermines traditional security measures that rely on MFA for account protection.

Infrastructure and Distribution

The platform's infrastructure consists of two main components: link domains and relay servers. Link domains handle initial phishing attempts, while relay servers are responsible for stealing credentials and completing login processes on behalf of the attacker. The relay servers are designed to mask their IP addresses by using proxy services, making it more difficult for security systems to block them [3].

Evasion Techniques

To evade detection by security tools, Mamba 2FA employs several strategies:

  • Sandbox Detection: The platform can detect if it is being analyzed in a sandbox environment and will redirect users to harmless pages like Google’s 404 error page.
  • Dynamic URL Generation: The URLs used in phishing attempts are frequently rotated and often short-lived to avoid being blacklisted by security solutions.
  • HTML Attachments: Phishing emails often include HTML attachments that appear benign but contain hidden JavaScript that redirects users to the phishing page [5].

Darktrace’s Coverage of Mamba 2FA

Starting in July 2024, the Darktrace Threat Research team detected a sudden rise in Microsoft 365 customer accounts logging in from unusual external sources. These accounts were accessed from an anomalous endpoint, 2607:5500:3000:fea[::]2, and exhibited unusual behaviors upon logging into Software-as-a-Service (SaaS) accounts. This activity strongly correlates with a phishing campaign using Mamba 2FA, first documented in late June 2024 and tracked as Mamba 2FA by Sekoia [2][3].

Darktrace / IDENTITY  was able to identify the initial stages of the Mamba 2FA campaign by correlating subtle anomalies, such as unusual SaaS login locations. Using AI based on peer group analysis, it detected unusual behavior associated with these attacks. By leveraging Autonomous Response actions, Darktrace was able to neutralize these threats in every instance of the campaign detected.

On July 23, a SaaS user was observed logging in from a rare ASN and IP address, 2607:5500:3000:fea::2, originating from the US and successfully passed through MFA authentication.

Figure 2: Model Alert Event Log showing Darktrace’s detection of a SaaS user mailbox logging in from an unusual source it correlates with Mamba 2FA relay server.

Almost an hour later, the SaaS user was observed logging in from another suspicious IP address, 45.133.172[.]86, linked to ASN AS174 COGENT-174. This IP, originating from the UK, successfully passed through MFA validation.

Following this unusual access, the SaaS user was notably observed reading emails and files that could contain sensitive payment and contract information. This behavior suggests that the attacker may have been leveraging contextual information about the target to craft further malicious phishing emails or fraudulent invoices. Subsequently, the user was detected creating a new mailbox rule titled 'fdsdf'. This rule was configured to redirect emails from a specific domain to the 'Deleted Items' folder and automatically mark them as read.

Implications of Unusual Email Rules

Such unusual email rule configurations are a common tactic employed by attackers. They often use these rules to automatically forward emails containing sensitive keywords—such as "invoice”, "payment", or "confidential"—to an external address. Additionally, these rules help conceal malicious activities, keeping them hidden from the target and allowing the attacker to operate undetected.

Figure 3: The model alert “SaaS / Compliance / Anomalous New Email Rule,” pertaining to the unusual email rule created by the SaaS user named ‘fdsdf’.

Blocking the action

A few minutes later, the SaaS user from the unusual IP address 45.133.172[.]86 was observed attempting to send an email with the subject “RE: Payments.” Subsequently, Darktrace detected the user engaging in activities that could potentially establish persistence in the compromised account, such as registering a new authenticator app. Recognizing this sequence of anomalous behaviors, Darktrace implemented an Autonomous Response inhibitor, disabling the SaaS user for two hours. This action effectively contained potential malicious activities, such as the distribution of phishing emails and fraudulent invoices, and gave the customer’s security team the necessary time to conduct a thorough investigation and implement appropriate security measures.

Figure 4: Device Event Log displaying Darktrace’s Autonomous Response taking action by blocking the SaaS account.
Figure 5: Darktrace / IDENTITY highlighting the 16 model alerts that triggered during the observed compromise.

In another example from mid-July, similar activities related to the campaign were observed on another customer network. A SaaS user was initially detected logging in from the unusual external endpoint 2607:5500:3000:fea[::]2.

Figure 6: The SaaS / Compromise / SaaS Anomaly Following Anomalous Login model alert was triggered by an unusual login from a suspicious IP address linked to Mamba 2FA.

A few minutes later, in the same manner as demonstrated in the previous case, the actor was observed logging in from another rare endpoint, 102.68.111[.]240. However, this time it was from a source IP located in Lagos, Nigeria, which no other user on the network had been observed connecting from. Once logged in, the SaaS user updated the settings to "User registered Authenticator App with Notification and Code," a possible attempt to maintain persistence in the SaaS account.

Figure 7: Darktrace / IDENTITY highlighted the regular locations for the SaaS user. The rarity scores associated with the Mamba 2FA IP location and another IP located in Nigeria were classified as having very low regularity scores for this user.

Based on unusual patterns of user behavior, a Cyber AI Analyst Incident was also generated, detailing all potential account hijacking activities. Darktrace also applied an Autonomous Response action, disabling the user for over five hours. This swift action was crucial in preventing further unauthorized access, potential data breaches and further implications.

Figure 8: Cyber AI Analyst Incident detailing the unusual activities related to the SaaS account hijacking.

Since the customer had subscribed to Darktrace Security Operations Centre (SOC) services, Darktrace analysts conducted an additional human investigation confirming the account compromise.

How Darktrace Combats Phishing Threats

The initial entry point for Mamba 2FA account compromises primarily involves phishing campaigns using HTML attachments and deceptive links. These phishing attempts are designed to mimic legitimate Microsoft services, such as OneDrive and SharePoint, making them appear authentic to unsuspecting users. Darktrace / EMAIL leverages multiple capabilities to analyze email content for known indicators of phishing. This includes looking for suspicious URLs, unusual attachments (like HTML files with embedded JavaScript), and signs of social engineering tactics commonly used in phishing campaigns like Mamba 2FA. With these capabilities, Darktrace successfully detected Mamba 2FA phishing emails in networks where this tool is integrated into the security layers, consequently preventing further implications and account hijacks of their users.

Mamba 2FA URL Structure and Domain Names

The URL structure used in Mamba 2FA phishing attempts is specifically designed to facilitate the capture of user credentials and MFA tokens while evading detection. These phishing URLs typically follow a pattern that incorporates Base64-encoded parameters, which play a crucial role in the operation of the phishing kit.

The URLs associated with Mamba 2FA phishing pages generally follow this structure [6]:

https://{domain}/{m,n,o}/?{Base64 string}

Below are some potential Mamba 2FA phishing emails, with the Base64 strings already decoded, that were classified as certain threats by Darktrace / EMAIL. This classification was based on identifying multiple suspicious characteristics, such as HTML attachments containing JavaScript code, emails from senders with no previous association with the recipients, analysis of redirect links, among others. These emails were autonomously blocked from being delivered to users' inboxes.

Figure 9: Darktrace / EMAIL highlighted a possible phishing email from Mamba 2FA, which was classified as a 100% anomaly.
Figure 10: Darktrace / EMAIL highlighted a URL that resembles the characteristics associated with Mamba 2FA.

Conclusion

The rise of PhaaS platforms and the advent of AiTM phishing kits represent a concerning evolution in cyber threats, pushing the boundaries of traditional phishing tactics and exposing significant vulnerabilities in current cybersecurity defenses. The ability of these attacks to effortlessly bypass traditional security measures like MFA underscores the need for more sophisticated, adaptive strategies to combat these evolving threats.

By identifying and responding to anomalous activities within Microsoft 365 accounts, Darktrace not only highlights the importance of comprehensive monitoring but also sets a new standard for proactive threat detection. Furthermore, the autonomous threat response capabilities and the exceptional proficiency of Darktrace / EMAIL in intercepting and neutralizing sophisticated phishing attacks illustrate a robust defense mechanism that can effectively safeguard users and maintain the integrity of digital ecosystems.

Credit to Patrick Anjos (Senior Cyber Analyst) and Nahisha Nobregas (Senior Cyber Analyst)

Get the latest insights on emerging cyber threats

Attackers are adapting, are you ready? This report explores the latest trends shaping the cybersecurity landscape and what defenders need to know in 2025.

  • Identity-based attacks: How attackers are bypassing traditional defenses
  • Zero-day exploitation: The rise of previously unknown vulnerabilities
  • AI-driven threats: How adversaries are leveraging AI to outmaneuver security controls

Stay ahead of evolving threats with expert analysis from Darktrace. Download the report here.

Appendices

Darktrace Model Detections

  • SaaS / Access / M365 High Risk Level Login
  • SaaS / Access / Unusual External Source for SaaS Credential Use
  • SaaS / Compromise / Login From Rare Endpoint While User Is Active
  • SaaS / Compliance / M365 Security Information Modified
  • SaaS / Compromise / Unusual Login and New Email Rule
  • SaaS / Email Nexus / Suspicious Internal Exchange Activity
  • SaaS / Compliance / Anomalous New Email Rule
  • SaaS / Email Nexus / Possible Outbound Email Spam
  • SaaS / Compromise / Unusual Login and Account Update
  • SaaS / Compromise / SaaS Anomaly Following Anomalous Login
  • SaaS / Compliance / M365 Security Information Modified
  • SaaS / Compromise / Login From Rare Endpoint While User Is Active
  • SaaS / Compromise / Unusual Login, Sent Mail, Deleted Sent
  • SaaS / Unusual Activity / Multiple Unusual SaaS Activities
  • SaaS / Email Nexus / Unusual Login Location Following Link to File Storage
  • SaaS / Unusual Activity / Multiple Unusual External Sources For SaaS Credential
  • IaaS / Compliance / Uncommon Azure External User Invite
  • SaaS / Compliance / M365 External User Added to Group
  • SaaS / Access / M365 High Risk Level Login
  • SaaS / Compliance / M365 Security Information Modified
  • SaaS/ Unusual Activity / Unusual MFA Auth and SaaS Activity
  • SaaS / Compromise / Unusual Login and Account Update

Cyber AI Analyst Incidents:

  • Possible Hijack of Office365 Account
  • Possible Hijack of AzureActiveDirectory Account
  • Possible Unsecured Office365 Resource

List of Indicators of Compromise (IoCs)

IoC       Type    Description + Confidence

2607:5500:3000:fea[::]2 - IPv6 - Possible Mamba 2FA relay server

2607:5500:3000:1cab:[:]2 - IPv6 - Possible Mamba 2FA relay server

References

1.     https://securityaffairs.com/136953/cyber-crime/caffeine-phishing-platform.html

2.     https://any.run/cybersecurity-blog/analysis-of-the-phishing-campaign/

3.     https://www.bleepingcomputer.com/news/security/new-mamba-2fa-bypass-service-targets-microsoft-365-accounts/

4.     https://cyberinsider.com/microsoft-365-accounts-targeted-by-new-mamba-2fa-aitm-phishing-threat/

5.     https://blog.sekoia.io/mamba-2fa-a-new-contender-in-the-aitm-phishing-ecosystem/

MITRE ATT&CK Mapping

Tactic – Technique

DEFENSE EVASION, PERSISTENCE, PRIVILEGE ESCALATION, INITIAL ACCESS - Cloud Accounts

DISCOVERY - Cloud Service Dashboard

RESOURCE DEVELOPMENT - Compromise Accounts

CREDENTIAL ACCESS - Steal Web Session Cookie

PERSISTENCE - Account Manipulation

PERSISTENCE - Outlook Rules

RESOURCE DEVELOPMENT - Email Accounts

INITIAL ACCESS - Phishing

Inside the SOC
Darktrace cyber analysts are world-class experts in threat intelligence, threat hunting and incident response, and provide 24/7 SOC support to thousands of Darktrace customers around the globe. Inside the SOC is exclusively authored by these experts, providing analysis of cyber incidents and threat trends, based on real-world experience in the field.
Written by
Patrick Anjos
Senior Cyber Analyst

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December 18, 2025

Why organizations are moving to label-free, behavioral DLP for outbound email

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Why outbound email DLP needs reinventing

In 2025, the global average cost of a data breach fell slightly — but remains substantial at USD 4.44 million (IBM Cost of a Data Breach Report 2025). The headline figure hides a painful reality: many of these breaches stem not from sophisticated hacks, but from simple human error: mis-sent emails, accidental forwarding, or replying with the wrong attachment. Because outbound email is a common channel for sensitive data leaving an organization, the risk posed by everyday mistakes is enormous.

In 2025, 53% of data breaches involved customer PII, making it the most commonly compromised asset (IBM Cost of a Data Breach Report 2025). This makes “protection at the moment of send” essential. A single unintended disclosure can trigger compliance violations, regulatory scrutiny, and erosion of customer trust –consequences that are disproportionate to the marginal human errors that cause them.

Traditional DLP has long attempted to mitigate these impacts, but it relies heavily on perfect labelling and rigid pattern-matching. In reality, data loss rarely presents itself as a neat, well-structured pattern waiting to be caught – it looks like everyday communication, just slightly out of context.

How data loss actually happens

Most data loss comes from frustratingly familiar scenarios. A mistyped name in auto-complete sends sensitive data to the wrong “Alex.” A user forwards a document to a personal Gmail account “just this once.” Someone shares an attachment with a new or unknown correspondent without realizing how sensitive it is.

Traditional, content-centric DLP rarely catches these moments. Labels are missing or wrong. Regexes break the moment the data shifts formats. And static rules can’t interpret the context that actually matters – the sender-recipient relationship, the communication history, or whether this behavior is typical for the user.

It’s the everyday mistakes that hurt the most. The classic example: the Friday 5:58 p.m. mis-send, when auto-complete selects Martin, a former contractor, instead of Marta in Finance.

What traditional DLP approaches offer (and where gaps remain)

Most email DLP today follows two patterns, each useful but incomplete.

  • Policy- and label-centric DLP works when labels are correct — but content is often unlabeled or mislabeled, and maintaining classification adds friction. Gaps appear exactly where users move fastest
  • Rule and signature-based approaches catch known patterns but miss nuance: human error, new workflows, and “unknown unknowns” that don’t match a rule

The takeaway: Protection must combine content + behavior + explainability at send time, without depending on perfect labels.

Your technology primer: The three pillars that make outbound DLP effective

1) Label-free (vs. data classification)

Protects all content, not just what’s labeled. Label-free analysis removes classification overhead and closes gaps from missing or incorrect tags. By evaluating content and context at send time, it also catches misdelivery and other payload-free errors.

  • No labeling burden; no regex/rule maintenance
  • Works when tags are missing, wrong, or stale
  • Detects misdirected sends even when labels look right

2) Behavioral (vs. rules, signatures, threat intelligence)

Understands user behavior, not just static patterns. Behavioral analysis learns what’s normal for each person, surfacing human error and subtle exfiltration that rules can’t. It also incorporates account signals and inbound intel, extending across email and Teams.

  • Flags risk without predefined rules or IOCs
  • Catches misdelivery, unusual contacts, personal forwards, odd timing/volume
  • Blends identity and inbound context across channels

3) Proprietary DSLM (vs. generic LLM)

Optimized for precise, fast, explainable on-send decisions. A DSLM understands email/DLP semantics, avoids generative risks, and stays auditable and privacy-controlled, delivering intelligence reliably without slowing mail flow.

  • Low-latency, on-send enforcement
  • Non-generative for predictable, explainable outcomes
  • Governed model with strong privacy and auditability

The Darktrace approach to DLP

Darktrace / EMAIL – DLP stops misdelivery and sensitive data loss at send time using hold/notify/justify/release actions. It blends behavioral insight with content understanding across 35+ PII categories, protecting both labeled and unlabeled data. Every action is paired with clear explainability: AI narratives show exactly why an email was flagged, supporting analysts and helping end-users learn. Deployment aligns cleanly with existing SOC workflows through mail-flow connectors and optional Microsoft Purview label ingestion, without forcing duplicate policy-building.

Deployment is simple: Microsoft 365 routes outbound mail to Darktrace for real-time, inline decisions without regex or rule-heavy setup.

A buyer’s checklist for DLP solutions

When choosing your DLP solution, you want to be sure that it can deliver precise, explainable protection at the moment it matters – on send – without operational drag.  

To finish, we’ve compiled a handy list of questions you can ask before choosing an outbound DLP solution:

  • Can it operate label free when tags are missing or wrong? 
  • Does it truly learn per user behavior (no shortcuts)? 
  • Is there a domain specific model behind the content understanding (not a generic LLM)? 
  • Does it explain decisions to both analysts and end users? 
  • Will it integrate with your label program and SOC workflows rather than duplicate them? 

For a deep dive into Darktrace’s DLP solution, check out the full solution brief.

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Carlos Gray
Senior Product Marketing Manager, Email

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December 17, 2025

Beyond MFA: Detecting Adversary-in-the-Middle Attacks and Phishing with Darktrace

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What is an Adversary-in-the-middle (AiTM) attack?

Adversary-in-the-Middle (AiTM) attacks are a sophisticated technique often paired with phishing campaigns to steal user credentials. Unlike traditional phishing, which multi-factor authentication (MFA) increasingly mitigates, AiTM attacks leverage reverse proxy servers to intercept authentication tokens and session cookies. This allows attackers to bypass MFA entirely and hijack active sessions, stealthily maintaining access without repeated logins.

This blog examines a real-world incident detected during a Darktrace customer trial, highlighting how Darktrace / EMAILTM and Darktrace / IDENTITYTM identified the emerging compromise in a customer’s email and software-as-a-service (SaaS) environment, tracked its progression, and could have intervened at critical moments to contain the threat had Darktrace’s Autonomous Response capability been enabled.

What does an AiTM attack look like?

Inbound phishing email

Attacks typically begin with a phishing email, often originating from the compromised account of a known contact like a vendor or business partner. These emails will often contain malicious links or attachments leading to fake login pages designed to spoof legitimate login platforms, like Microsoft 365, designed to harvest user credentials.

Proxy-based credential theft and session hijacking

When a user clicks on a malicious link, they are redirected through an attacker-controlled proxy that impersonates legitimate services.  This proxy forwards login requests to Microsoft, making the login page appear legitimate. After the user successfully completes MFA, the attacker captures credentials and session tokens, enabling full account takeover without the need for reauthentication.

Follow-on attacks

Once inside, attackers will typically establish persistence through the creation of email rules or registering OAuth applications. From there, they often act on their objectives, exfiltrating sensitive data and launching additional business email compromise (BEC) campaigns. These campaigns can include fraudulent payment requests to external contacts or internal phishing designed to compromise more accounts and enable lateral movement across the organization.

Darktrace’s detection of an AiTM attack

At the end of September 2025, Darktrace detected one such example of an AiTM attack on the network of a customer trialling Darktrace / EMAIL and Darktrace / IDENTITY.

In this instance, the first indicator of compromise observed by Darktrace was the creation of a malicious email rule on one of the customer’s Office 365 accounts, suggesting the account had likely already been compromised before Darktrace was deployed for the trial.

Darktrace / IDENTITY observed the account creating a new email rule with a randomly generated name, likely to hide its presence from the legitimate account owner. The rule marked all inbound emails as read and deleted them, while ignoring any existing mail rules on the account. This rule was likely intended to conceal any replies to malicious emails the attacker had sent from the legitimate account owner and to facilitate further phishing attempts.

Darktrace’s detection of the anomalous email rule creation.
Figure 1: Darktrace’s detection of the anomalous email rule creation.

Internal and external phishing

Following the creation of the email rule, Darktrace / EMAIL observed a surge of suspicious activity on the user’s account. The account sent emails with subject lines referencing payment information to over 9,000 different external recipients within just one hour. Darktrace also identified that these emails contained a link to an unusual Google Drive endpoint, embedded in the text “download order and invoice”.

Darkrace’s detection of an unusual surge in outbound emails containing suspicious content, shortly following the creation of a new email rule.
Figure 2: Darkrace’s detection of an unusual surge in outbound emails containing suspicious content, shortly following the creation of a new email rule.
Darktrace / EMAIL’s detection of the compromised account sending over 9,000 external phishing emails, containing an unusual Google Drive link.
Figure 3: Darktrace / EMAIL’s detection of the compromised account sending over 9,000 external phishing emails, containing an unusual Google Drive link.

As Darktrace / EMAIL flagged the message with the ‘Compromise Indicators’ tag (Figure 2), it would have been held automatically if the customer had enabled default Data Loss Prevention (DLP) Action Flows in their email environment, preventing any external phishing attempts.

Figure 4: Darktrace / EMAIL’s preview of the email sent by the offending account.
Figure 4: Darktrace / EMAIL’s preview of the email sent by the offending account.

Darktrace analysis revealed that, after clicking the malicious link in the email, recipients would be redirected to a convincing landing page that closely mimicked the customer’s legitimate branding, including authentic imagery and logos, where prompted to download with a PDF named “invoice”.

Figure 5: Download and login prompts presented to recipients after following the malicious email link, shown here in safe view.

After clicking the “Download” button, users would be prompted to enter their company credentials on a page that was likely a credential-harvesting tool, designed to steal corporate login details and enable further compromise of SaaS and email accounts.

Darktrace’s Response

In this case, Darktrace’s Autonomous Response was not fully enabled across the customer’s email or SaaS environments, allowing the compromise to progress,  as observed by Darktrace here.

Despite this, Darktrace / EMAIL’s successful detection of the malicious Google Drive link in the internal phishing emails prompted it to suggest ‘Lock Link’, as a recommended action for the customer’s security team to manually apply. This action would have automatically placed the malicious link behind a warning or screening page blocking users from visiting it.

Autonomous Response suggesting locking the malicious Google Drive link sent in internal phishing emails.
Figure 6: Autonomous Response suggesting locking the malicious Google Drive link sent in internal phishing emails.

Furthermore, if active in the customer’s SaaS environment, Darktrace would likely have been able to mitigate the threat even earlier, at the point of the first unusual activity: the creation of a new email rule. Mitigative actions would have included forcing the user to log out, terminating any active sessions, and disabling the account.

Conclusion

AiTM attacks represent a significant evolution in credential theft techniques, enabling attackers to bypass MFA and hijack active sessions through reverse proxy infrastructure. In the real-world case we explored, Darktrace’s AI-driven detection identified multiple stages of the attack, from anomalous email rule creation to suspicious internal email activity, demonstrating how Autonomous Response could have contained the threat before escalation.

MFA is a critical security measure, but it is no longer a silver bullet. Attackers are increasingly targeting session tokens rather than passwords, exploiting trusted SaaS environments and internal communications to remain undetected. Behavioral AI provides a vital layer of defense by spotting subtle anomalies that traditional tools often miss

Security teams must move beyond static defenses and embrace adaptive, AI-driven solutions that can detect and respond in real time. Regularly review SaaS configurations, enforce conditional access policies, and deploy technologies that understand “normal” behavior to stop attackers before they succeed.

Credit to David Ison (Cyber Analyst), Bertille Pierron (Solutions Engineer), Ryan Traill (Analyst Content Lead)

Appendices

Models

SaaS / Anomalous New Email Rule

Tactic – Technique – Sub-Technique  

Phishing - T1566

Adversary-in-the-Middle - T1557

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About the author
David Ison
Cyber Analyst
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