ブログ
/
AI
/
April 30, 2024

Detecting Attacks Across Email, SaaS, and Network Environments with Darktrace’s ActiveAI Security Platform

This blog explores how Darktrace’s combined AI approach enabled it to identify and connect an attack that took place over three critical areas of a customer’s digital environment, namely email, SaaS and network.
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
30
Apr 2024

The State of AI in Cybersecurity

In a recent survey outlined in Darktrace’s State of AI Cyber Security whitepaper, 95% of cyber security professionals agree that AI-powered security solutions will improve their organization’s detection of cyber-threats [1]. Crucially, a combination of multiple AI methods is the most effective to improve cybersecurity; improving threat detection, accelerating threat investigation and response, and providing visibility across an organization’s digital environment.

In March 2024, Darktrace’s AI-led security platform was able to detect suspicious activity affecting a customer’s email, Software-as-a-Service (SaaS), and network environments, whilst its applied supervised learning capability, Cyber AI Analyst, autonomously correlated and connected all of these events together in one single incident, explained concisely using natural language processing.

Attack Overview

Following an initial email attack vector, an attacker logged into a compromised SaaS user account from the Netherlands, changed inbox rules, and leveraged the account to send thousands of phishing emails to internal and external users. Internal users fell victim to the emails by clicking on contained suspicious links that redirected them to newly registered suspicious domains hosted on same IP address as the hijacked SaaS account login. This activity triggered multiple alerts in Darktrace DETECT™ on both the network and SaaS side, all of which were correlated into one Cyber AI Analyst incident.

In this instance, Darktrace RESPOND™ was not active on any of the customer’s environments, meaning the compromise was able to escalate until their security team acted on the alerts raised by DETECT. Had RESPOND been enabled at the time of the attack, it would have been able to apply swift actions to contain the attack by blocking connections to suspicious endpoints on the network side and disabling users deviating from their normal behavior on the customer’s SaaS environment.

Nevertheless, thanks to DETECT and Cyber AI Analyst, Darktrace was able to provide comprehensive visibility across the customer’s three digital estate environments, decreasing both investigation and response time which enabled them to quickly enact remediation during the attack. This highlights the crucial role that Darktrace’s combined AI approach can play in anomaly detection cyber defense

Attack Details & Darktrace Coverage

Attack timeline

1. Email: the initial attack vector  

The initial attack vector was likely email, as on March 18, 2024, Darktrace observed a user device making several connections to the email provider “zixmail[.]net”, shortly before it connected to the first suspicious domain. Darktrace/Email identified multiple unusual inbound emails from an unknown sender that contained a suspicious link. Darktrace recognized these emails as potentially malicious and locked the link, ensuring that recipients could not directly click it.

Figure 1: Suspected initial compromise email from an unknown sender, containing a suspicious link, which was locked by Darktrace/Email.

2. Escalation to Network

Later that day, despite Darktrace/Email having locked the link in the suspicious email, the user proceeded to click on it and was directed to a suspicious external location, namely “rz8js7sjbef[.]latovafineart[.]life”, which triggered the Darktrace/Network DETECT model “Suspicious Domain”. Darktrace/Email was able to identify that this domain had only been registered 4 days before this activity and was hosted on an IP address based in the Netherlands, 193.222.96[.]9.

3. SaaS Account Hijack

Just one minute later, Darktrace/Apps observed the user’s Microsoft 365 account logging into the network from the same IP address. Darktrace understood that this represented unusual SaaS activity for this user, who had only previously logged into the customer’s SaaS environment from the US, triggering the “Unusual External Source for SaaS Credential Use” model.

4. SaaS Account Updates

A day later, Darktrace identified an unusual administrative change on the user’s Microsoft 365 account. After logging into the account, the threat actor was observed setting up a new multi-factor authentication (MFA) method on Microsoft Authenticator, namely requiring a 6-digit code to authenticate. Darktrace understood that this authentication method was different to the methods previously used on this account; this, coupled with the unusual login location, triggered the “Unusual Login and Account Update” DETECT model.

5. Obfuscation Email Rule

On March 20, Darktrace detected the threat actor creating a new email rule, named “…”, on the affected account. Attackers are typically known to use ambiguous or obscure names when creating new email rules in order to evade the detection of security teams and endpoints users.

The parameters for the email rule were:

“AlwaysDeleteOutlookRulesBlob: False, Force: False, MoveToFolder: RSS Feeds, Name: ..., MarkAsRead: True, StopProcessingRules: True.”

This rule was seemingly created with the intention of obfuscating the sending of malicious emails, as the rule would move sent emails to the "RSS Feeds” folder, a commonly used tactic by attackers as the folder is often left unchecked by endpoint users. Interestingly, Darktrace identified that, despite the initial unusual login coming from the Netherlands, the email rule was created from a different destination IP, indicating that the attacker was using a Virtual Private Network (VPN) after gaining a foothold in the network.

Hijacked SaaS account making an anomalous login from the unusual Netherlands-based IP, before creating a new email rule.
Figure 2: Hijacked SaaS account making an anomalous login from the unusual Netherlands-based IP, before creating a new email rule.

6. Outbound Phishing Emails Sent

Later that day, the attacker was observed using the compromised customer account to send out numerous phishing emails to both internal and external recipients. Darktrace/Email detected a significant spike in inbound emails on the compromised account, with the account receiving bounce back emails or replies in response to the phishing emails. Darktrace further identified that the phishing emails contained a malicious DocSend link hidden behind the text “Click Here”, falsely claiming to be a link to the presentation platform Prezi.

Figure 3: Darktrace/Email detected that the DocSend link displayed via text “Click Here”, was embedded in a Prezi link.
Figure 3: Darktrace/Email detected that the DocSend link displayed via text “Click Here”, was embedded in a Prezi link.

7. Suspicious Domains and Redirects

After the phishing emails were sent, multiple other internal users accessed the DocSend link, which directed them to another suspicious domain, “thecalebgroup[.]top”, which had been registered on the same day and was hosted on the aforementioned Netherlands-based IP, 193.222.96[.]91. At the time of the attack, this domain had not been reported by any open-source intelligence (OSINT), but it has since been flagged as malicious by multiple vendors [2].

External Sites Summary showing the suspicious domain that had never previously been seen on the network. A total of 11 “Suspicious Domain” models were triggered in response to this activity.
Figure 4: External Sites Summary showing the suspicious domain that had never previously been seen on the network. A total of 11 “Suspicious Domain” models were triggered in response to this activity.  

8. Cyber AI Analyst’s Investigation

As this attack was unfolding, Darktrace’s Cyber AI Analyst was able to autonomously investigate the events, correlating them into one wider incident and continually adding a total of 14 new events to the incident as more users fell victim to the phishing links.

Cyber AI Analyst successfully weaved together the initial suspicious domain accessed in the initial email attack vector (Figure 5), the hijack of the SaaS account from the Netherlands IP (Figure 6), and the connection to the suspicious redirect link (Figure 7). Cyber AI Analyst was also able to uncover other related activity that took place at the time, including a potential attempt to exfiltrate data out of the customer’s network.

By autonomously analyzing the thousands of connections taking place on a network at any given time, Darktrace’s Cyber AI Analyst is able to detect seemingly separate anomalous events and link them together in one incident. This not only provides organizations with full visibility over potential compromises on their networks, but also saves their security teams precious time ensuring they can quickly scope out the ongoing incident and begin remediation.

Figure 5: Cyber AI Analyst correlated the attack’s sequence, starting with the initial suspicious domain accessed in the initial email attack vector.
Figure 5: Cyber AI Analyst correlated the attack’s sequence, starting with the initial suspicious domain accessed in the initial email attack vector.
Figure 6: As the attack progressed, Cyber AI Analyst correlated and appended additional events to the same incident, including the SaaS account hijack from the Netherlands-based IP.
Figure 6: As the attack progressed, Cyber AI Analyst correlated and appended additional events to the same incident, including the SaaS account hijack from the Netherlands-based IP.
Cyber AI Analyst correlated and appended additional events to the same incident, including additional users connecting to the suspicious redirect link following the outbound phishing emails being sent.
Figure 7: Cyber AI Analyst correlated and appended additional events to the same incident, including additional users connecting to the suspicious redirect link following the outbound phishing emails being sent.

Conclusion

In this scenario, Darktrace demonstrated its ability to detect and correlate suspicious activities across three critical areas of a customer’s digital environment: email, SaaS, and network.

It is essential that cyber defenders not only adopt AI but use a combination of AI technology capable of learning and understanding the context of an organization’s entire digital infrastructure. Darktrace’s anomaly-based approach to threat detection allows it to identify subtle deviations from the expected behavior in network devices and SaaS users, indicating potential compromise. Meanwhile, Cyber AI Analyst dynamically correlates related events during an ongoing attack, providing organizations and their security teams with the information needed to respond and remediate effectively.

Credit to Zoe Tilsiter, Analyst Consulting Lead (EMEA), Brianna Leddy, Director of Analysis

Appendices

References

[1] https://darktrace.com/state-of-ai-cyber-security

[2] https://www.virustotal.com/gui/domain/thecalebgroup.top

Darktrace DETECT Model Coverage

SaaS Models

- SaaS / Access / Unusual External Source for SaaS Credential Use

- SaaS / Compromise / Unusual Login and Account Update

- SaaS / Compliance / Anomalous New Email Rule

- SaaS / Compromise / Unusual Login and New Email Rule

Network Models

- Device / Suspicious Domain

- Multiple Device Correlations / Multiple Devices Breaching Same Model

Cyber AI Analyst Incidents

- Possible Hijack of Office365 Account

- Possible SSL Command and Control

Indicators of Compromise (IoCs)

IoC – Type – Description

193.222.96[.]91 – IP – Unusual Login Source

thecalebgroup[.]top – Domain – Possible C2 Endpoint

rz8js7sjbef[.]latovafineart[.]life – Domain – Possible C2 Endpoint

https://docsend[.]com/view/vcdmsmjcskw69jh9 - Domain - Phishing Link

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

Default 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

Default 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
あなたのデータ × DarktraceのAI
唯一無二のDarktrace AIで、ネットワークセキュリティを次の次元へ