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June 9, 2021

Multi-Account Hijack Detection with AI

Discover the analysis of a sophisticated SaaS-based attack using Microsoft 365 accounts. Learn how attackers launch & maintain their offensive strategies.
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
Max Heinemeyer
Global Field CISO
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09
Jun 2021

The widespread and rapid adoption of Software-as-a-Service (SaaS) has opened up a breadth of security risks for IT teams. Unlike commercial off-the-shelf (COTS) software, SaaS security tends to be managed by third-party vendors rather than the end customer. Security teams therefore struggle with reduced visibility and control over these environments, and cyber-criminals have been quick to take advantage, launching a wave of cloud-based attacks, from Vendor Email Compromise to internal account hijacks.

Attackers often gain access to multiple accounts on the same domain, enabling them to attack from multiple angles, for example sending of hundreds of emails from one account, while maintaining persistence with another. This gives the hacker an opportunity to try multiple attack vectors, using tools native to the SaaS environment as well as external payloads.

While preventative controls such as Multi-Factor Authentication (MFA) provide an extra layer of protection, there are many techniques available to circumvent zero-trust approaches. Remote and flexible working is set to continue to varying degrees across many different regions and industries, so companies must now commit to securing their cloud architecture and developing proactive cyber security measures.

In this blog, we will analyze a persistent cyber-attack which targeted a real estate company in Europe and leveraged several compromised Microsoft 365 accounts. These SaaS takeovers are quickly becoming the new norm, but they are still misunderstood and poorly documented in the wider industry. Cyber AI detected every stage of this intrusion in real time, without the use of signatures or static rules.

A and B: Hijacking Microsoft 365 accounts

The organization had around 5,000 devices in its environment, with 1,000 active SaaS accounts. The timeline below shows how the threat actor leveraged the SaaS accounts of five different users to carry out the operation, as well as exploiting several other accounts on the final day.

Figure 1: Diagram of the infection chain, which occurred over three days. On the fourth day, the attacker tried again but was unsuccessful.

The actor initially compromised at least two SaaS credentials – which we’ll refer to here simply as ‘account A’ and ‘account B’ – and logged in from several unusual geographical locations, presumably using a VPN. Darktrace detected this as unusual login events for the SaaS accounts.

In account A, the attacker was observed previewing files likely to contain customer information, but did not perform any other follow-up activity. In account B, they set a new inbox rule three hours after the initial compromise, resulting in a high-severity alert.

At around this time, the threat actor sent a number of phishing emails from account B: emails that appeared to be sharing a harmless and legitimate-looking folder on OneDrive. The link probably led to a fake Microsoft login page, similar to the below, which could have recorded the victims’ credentials and sent them directly back to the attacker.

Figure 2: A seemingly legitimate Microsoft login page.

The phishing attempt was detected by Antigena Email, Darktrace’s email security technology. Antigena was in passive mode at the time, and so was not configured to take action on these threatening emails. But taking into account the highly anomalous sender surge coupled with the unusual login locations, it would have autonomously intercepted all the emails, reducing the impact of the attack.

The attacker was subsequently locked out of account B. After this, they tried (and failed) to use a legacy user agent to bypass any MFA which may have been enforced on the account. Darktrace detected this as a suspicious login and blocked the attempt.

Accounts C, D and E: The threat develops

The next day, the actor logged into a new account (account C) from the same autonomous system number (ASN), indicating that the account had been infected by the OneDrive phishing emails. In other words, the attacker had leveraged account B to compromise new users in the organization and ensure multiple points of intrusion.

Darktrace detected each stage of this, piecing together the different events into one meaningful security narrative.

Figure 3: Anomalous activity from accounts C, D, and E.

Account C was then used to preview a file likely containing contact information.

After being locked out of account C when trying to log in the next day, the hacker worked their way through two more accounts (account D and account E), which they had hijacked in the previous phishing attempts. They were locked out each time after generating alerts due to the unusual logins and new inbox rules created around the same time.

A to Z: End of the line

Running out of options, the attacker decided to go back to account A and set a new inbox rule, using it to send new phishing emails with a link to a non-Microsoft cloud storage domain (Tresorit). Again, Darktrace recognized this as highly unusual behavior, and the hacker was promptly locked out of the account.

During this burst of activity, Darktrace also observed a Microsoft Teams session from one of the suspicious ASNs. This was likely a social engineering attempt and another possible attack vector. Microsoft Teams could have been leveraged to share a malicious link over instant message, extract sensitive information, or send spam internally and externally on the chat function.

The threat actor could have then used this to pivot across various applications and accounts, assuming that the company had a siloed security approach – with different tools for cloud, SaaS, email, and endpoint – and so could not pick up on the malicious cross-platform movement.

On the following day, the attacker attempted logins on multiple accounts again, but with no success. Cyber AI had pinpointed all the anomalous activity – no matter where it originated – and alerted the security team immediately.

SaaS attack under the microscope

Multi-account compromises can be incredibly persistent and are difficult for traditional security tools to identify. The hacker used several tactics to circumvent the customer’s existing email security products:

  1. The initial use of two compromised credentials – account A and account B – allowed the hacker to stay under the radar and not raise too much suspicion on a single account. Account A was kept quiet until other avenues had been exhausted.
  2. Activity was generated from multiple ASNs in at least three different geographical locations, probably utilizing a VPN: one in Africa where much of the activity originated, and two in North America, including some widely used ASNs which were highly unusual for the customer.
  3. The attacker entirely used Microsoft services until the final emails, choosing to ‘live off the land’ rather than sending links that may have been caught by gateways.
  4. The attacker logged into Microsoft Teams in their final movements – a fairly benign-looking event which could have been used to compromise more accounts and move laterally, and would have gone undetected.

Darktrace identified every stage of the attack – including spotting the anomalous ASNs – and launched an automatic, in-depth investigation with Cyber AI Analyst. The organization was thus able to take action before the damage was done.

Figure 4: Darktrace’s SaaS console gives a clear overview of activity across all different applications.

ABCs of SaaS security

The approach of using various accounts to mount the offensive, while keeping one to maintain persistence, prolonged this intrusion. Such tactics will likely be seen again in the near future.

Tracking the number of factors involved in an attack with multiple credentials, multiple attack vectors, and multiple attacker-IPs, is a serious challenge. In these situations, it is essential to have a security solution which can detect activity across different applications, forming a unified and holistic understanding over the entire digital enterprise.

While not active in this case, Antigena SaaS would have taken autonomous action and prevented the threat from escalating by enforcing normal behavior, stopping the hacker from logging in from malicious infrastructure or performing any out-of-character SaaS actions, such as creating new inbox rules.

Following the intrusion, the company decided to adopt Antigena SaaS, which now mitigates their cloud security risks and guards against sensitive data loss and reputational damage.

Thanks to Darktrace analyst Daniel Gentle for his insights on the above threat find.

Darktrace model detections:

  • SaaS / Compromise / Unusual Login and New Email Rule
  • SaaS / Compliance / New Email Rule
  • SaaS / Unusual Activity / Unusual External Source for SaaS Credential Use
  • SaaS / Access / Suspicious Login Attempt
  • Antigena Email: Unusual Login Location + Sender Surge
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
Max Heinemeyer
Global Field CISO

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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.

[related-resource]

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About the author
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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