Blog
/
Identity
/
May 19, 2023

Darktrace Stops Large-Scale Account Hijack

Learn how Darktrace detected and stopped a large-scale account hijack that led to a phishing attack. Protect your business with these insights.
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
Zoe Tilsiter
Cyber Analyst
Default blog imageDefault blog imageDefault blog imageDefault blog imageDefault blog imageDefault blog image
19
May 2023

Introduction 

As malicious actors across the threat landscape continue to take advantage of the widespread adoption of Software-as-a-Service (SaaS) platforms and multi-factor authentication (MFA) services to gain unauthorized access to organizations’ networks, it is crucial to have appropriate security tools in place to defend against account compromise at the earliest stage.

One method frequently employed by attackers is account takeover. Account takeovers occur when a threat actor exploits credentials to login to a SaaS account, often from an unusual location where the genuine actor does not usually login from. 

Access to these accounts can be caused by harvesting credentials through phishing emails and password spray attacks, or by exploiting insecure cloud safety practices such as not having MFA enabled on user accounts, requiring only user credentials for authentication. Once the integrity of the account is compromised, the threat actor can conduct further activity, such as delivering malware, reading and exfiltrating sensitive data, and sending out phishing emails to harvest further internal and external user credentials, repeating the attack cycle [1,2]. 

In early 2023, Darktrace detected a large-scale account takeover and phishing attack on the network of a customer in the education sector that affected hundreds of accounts and resulted in thousands of emails being forwarded outside of the network. The exceptional degree of visibility provided by Darktrace DETECT™ allowed for the detection of adversarial activity at every stage of the kill chain, and direct support from the Darktrace Analyst team via the Ask the Expert (ATE) service ensured the customer was fully informed and equipped to implement remedial action. 

Details of Attack Chain

Darktrace observed the same pattern of activity on all hijacked accounts on the customer’s network; login from unfamiliar locations, enablement of a mail forwarding rule that forwards all incoming emails to malicious email addresses, and the sending of phishing emails followed by their deletion. 

Figure 1: Timeline of attack on hijacked SaaS accounts.

Initial Access

Darktrace DETECT first detected anomalous SaaS activity on the customer environment on January 14, 2023, and then again on February 3, when multiple SaaS accounts were observed logging in from atypical locations with rare IP addresses and geographically impossible travel timings, or logging in whilst the account owner was active elsewhere. Subsequent investigation using open-source intelligence (OSINT) sources revealed one of the IP addressed had recently been associated with brute-force or password spray attempt.

This pattern of unusual login behavior persisted throughout the timeframe of the attack, with more unique accounts generating model breaches each day for similarly anomalous logins. As MFA authentication was not enforced for these user logins, the initial intrusion process was enabled by requiring only credentials for authentication.

Sending Emails 

The compromised accounts were also seen sending out emails with the subject ‘Email HELP DESK’ to external and internal recipients. This was likely represented a threat actor employing social engineering tactics to gain the trust of the recipient by posing as an internal help desk.

Mail Forwarding

Following the successful logins, compromised accounts began creating email rules to forward mail to external email addresses, some of which were associated with domains that had hits for malicious activity according to OSINT sources [3].

  • chotunai[.]com
  • bymercy[.]com
  • breazeim[.]com
  • brandoza[.]com

Forwarding mail is a commonly observed tactic during SaaS compromises to control lines of communication. Malicious actors often attempt to insert themselves into ongoing correspondence for illicit purposes, such as exfiltrating sensitive information, gaining persistent access to the compromised email or redirecting invoice payments. 

Email Deletions

Shortly after the mail forwarding activity, compromised accounts were detected performing anomalous email deletions en masse. Further investigation revealed that these accounts had previously sent a large volume of phishing emails and this mass deletion likely represented an attempt to conceal these activities by deleting them from their outboxes.

On February 10, the customer applied a mass password reset on all accounts that Darktrace had identified as compromised and provisioned, privileged accounts with MFA. They have indicated that those measures successfully halted the compromise, addressing the initial point of entry.  

Darktrace Coverage

Using its Self-Learning AI, Darktrace effectively demonstrated its ability to detect unusual SaaS activity that could indicate that an account has been hijacked by malicious actors. Rather than relying on a traditional rules and signature-based approach, Darktrace models develop an understanding of the network itself and can instantly recognize when a compromised deviates from its expected pattern of life.

Figure 2: Detection of unusual SaaS activity on hijacked SaaS account.

Initial Access

Initial access was detected by the following models:

  • Security Integration / High Severity Integration Detection  
  • SaaS / Unusual Activity / Activity from Multiple Unusual IPs 
  • SaaS / Access / Unusual External Source for SaaS Credential Use 
  • SaaS / Compromise / Login From Rare Endpoint While User Is Active 

Initial access was also detected by the following Cyber AI Analyst Incidents:

  • Possible Hijack of Office365 Account 

The model breaches and AI Analyst incidents detected logins from 100% rare external IP addresses in conjunction with a lack of MFA usage, as depicted in Figure 3.

Figure 3: Breach log showing initial detection of a SaaS login from a 100% rare IP where MFA was not used.
Figure 4: Initial detection of unusual SaaS activity visualized in Darktrace's SaaS console.

Mail Forwarding

Mail forwarding was detected by the following models:

  • SaaS / Admin / Mail Forwarding Enabled 

Compromised accounts were largely detected configuring mail forwarding rules to external email addresses, ostensibly to establish persistence on the network and exfiltrate sensitive correspondence.

Figure 5: The enablement of mail forwarding was detected as 100% new or uncommon for the account in question.

Mass Email Deletion

Mass email deletion was detected by the following models:

  • SaaS / Compromise / Suspicious Login and Mass Email Deletes 
  • SaaS / Resource / Mass Email Deletes from Rare Location 
Figure 6: Compromised account deleting phishing emails it had previously sent from the outbox.

Darktrace detected accounts performing highly anomalous mass email deletions from rare locations. The actors deleted the email “Email HELP DESK” which was later confirmed as being the primary phishing email used in the attack. Deletions were observed on compromised accounts’ outboxes, presumably to conceal the malicious activity.

Darktrace also detected this linked pattern of activity in sequential models such as: 

  • SaaS / Compromise / Unusual Login, Sent Mail, Deleted Sent
  • SaaS / Compromise / Suspicious Login and Mass Email Deletes 

Ask the Expert

The customer used the ATE service to request more technical information and support concerning the attack. Darktrace’s 24/7 team of analysts were able to offer expert assistance and further details to assist in the subsequent investigations and remediation steps. 

Further Detection and Response  

Unfortunately, the customer did not have Darktrace/Email™ enabled at the time of the attack. Darktrace/Email has visibility over inbound and outbound mail-flow which provides an oversight on potential data loss incidents. In this case, Darktrace DETECT/Email would have been able to provide full visibility over the phishing emails sent by the compromised accounts, as well as the attackers attempts to spoof an internal helpdesk. Further to this, the new Analysis Outlook integration helps employees understand why an email is suspicious and enables them report emails directly to the security team, which helps to continuously build user awareness of phishing attacks. 

Darktrace/Email also enhances Darktrace/Network™ detections by triggering ‘Email Nexus’ models within Darktrace/Network, where malicious activity is detected across the digital estate, correlating moving from SaaS compromised logins to mass email spam being sent out by compromised users

Figure 7: Email Nexus models within the Darktrace/Network enhanced by Darktrace/Email

Darktrace RESPOND™ was not enabled on the customer environment at the time of the attack; if it were, Darktrace would have been able to autonomously take action against the SaaS model breaches detecting across multiple of the kill chain. RESPOND would have disabled the hijacked accounts or force them to log out for a period of time, whilst also disabling the inbox rules that had been established by malicious actors. This would have given the customer’s security team valuable time to analyze the incident and mitigate the situation, preventing the attack from escalating any further. 

Conclusion

Ultimately, Darktrace demonstrated its unparalleled visibility over customer networks which allowed for the detection of this large-scale targeted SaaS account takeover, and the subsequent phishing attack. It underscores the importance of defense in depth; critically, MFA was not enforced for this environment which likely made the targeted organization far more susceptible to compromise via credential theft. The phishing activity detected by Darktrace following this account compromise also highlights the need for email protection in any security stack. 

Darktrace’s visibility meant allowed it to detect the attack at a high degree of granularity, including the account logins, email forwarding rule creations, outbound mail, and the mass deletions of phishing emails. Darktrace’s anomaly-based detection means it does not have to rely on signatures, rules or known indicators of compromise (IoCs) when identifying an emerging threat, instead placing the emphasis on recognizing a user’s deviation from its normal behavior.

However, without the presence of an autonomous response technology able to instantly intervene and stop ongoing attacks, organizations will always be reacting to attacks once the damage is done. Darktrace RESPOND is uniquely placed to take action against suspicious activity as soon as it is detected, preventing attacks from escalating and saving customers from significant disruption to their business.

Credit to: Zoe Tilsiter, Cyber Analyst, Gernice Lee, Cyber Analyst.

Appendices

Models Breached

SaaS / Access / Unusual External Source for SaaS Credential Use

SaaS / Admin / Mail Forwarding Enabled

SaaS / Compliance / Microsoft Cloud App Security Alert Detected

SaaS / Compromise / SaaS Anomaly Following Anomalous Login 

SaaS / Compromise / Unusual Login, Sent Mail, Deleted Sent

SaaS / Compromise / Suspicious Login and Mass Email Deletes 

SaaS / Resource / Mass Email Deletes from Rare Location

SaaS / Unusual Activity / Multiple Unusual External Sources For SaaS Credential

SaaS / Unusual Activity / Activity from Multiple Unusual IPs

SaaS / Unusual Activity / Multiple Unusual SaaS Activities 

Security Integration / Low Severity Integration Detection

Security Integration / High Severity Integration Detection

List of IoCs

brandoza[.]com - domain - probable domain of forwarded email address

breazeim[.]com - domain - probable domain of forwarded email address

bymercy[.]com - domain - probable domain of forwarded email address

chotunai[.]com - domain - probable domain of forwarded email address

MITRE ATT&CK Mapping

Tactic: INITIAL ACCESS, PERSISTENCE, PRIVILEGE ESCILATION, DEFENSE EVASION

Technique: T1078.004 – Cloud Accounts

Tactic: COLLECTION

Technique: T1114- Email Collection

Tactic:COLLECTION

Technique: T1114.003- Email Forwarding Rule

Tactic: IMPACT

Technique: T1485- Data Destruction

Tactic: DEFENSE EVASION

Technique: T1578.003 – Delete Cloud Instance

References

[1] Darktrace, 2022, Cloud Application Security_ Protect your SaaS with Self-Learning AI.pdf

[2] https://www.cloudflare.com/en-gb/learning/access-management/account-takeover/ 

[3] https://www.virustotal.com/gui/domain/chotunai.com 

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
Zoe Tilsiter
Cyber Analyst

More in this series

No items found.

Blog

/

Email

/

December 18, 2025

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

Man at laptopDefault blog imageDefault blog image

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]

Continue reading
About the author
Carlos Gray
Senior Product Marketing Manager, Email

Blog

/

Email

/

December 17, 2025

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

Beyond MFA: Detecting Adversary-in-the-Middle Attacks and Phishing with DarktraceDefault blog imageDefault blog image

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

Continue reading
About the author
Your data. Our AI.
Elevate your network security with Darktrace AI