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.
Figure 1: An interactive snapshot of Antigena Email’s user interface
Antigena Email recently detected a malicious email sent from a legitimate corporate email account – presumably that of a supplier – that had been subject to an account takeover. The email claimed to be a ShareFile notification, but contained links to malicious domains previously associated with phishing attacks. These webpages are commonly designed to trick users into downloading malware or leaking sensitive corporate information.
Figure 2: A subset of the breached models and associated actions
Why was this attack effective?
This attack combined an account takeover with a typical impersonation attack. At first glance, all of the email’s elements appear legitimate, from the ShareFile notification, to the genuine and trusted corporate email address, to the subject line.
The email contained an additional misleading link featuring an email address seemingly associated with the recipient, but that also redirected a user to a malicious webpage. Believing that the email contained genuine ShareFile content, given past legitimate business interactions with the supplier, a user may have easily clicked on one of the malicious links and entered sensitive information on the phishing page.
Sender information
The sender’s name was listed as “share_file®”, but the email address was associated with a compromised account from a Ukrainian electronic components company.
Why did this attack bypass other email security solutions?
As the email came from a genuine corporation and trusted supplier known to the organization, it would have passed the Sender Policy Framework (SPF) authentication technique and been considered legitimate. The fact that the account sending the email had not yet been reported as compromised meant that the email was not flagged as spam by traditional security solutions, and would have been able to distribute malicious content to employees.
AI email security that evolves with you
Antigena Email recognized that the suspicious link in the email fell outside of both the sender and recipient’s normal ‘patterns of life.’ The AI took the strongest possible action, preventing the targets from engaging with the email and malicious link contained within. Compromised accounts can be some of the most difficult attacks to detect, because of the trusted relationships that exist with other organizations. This attack demonstrates the power of AI email security that continuously evolves with a business.
Thanks to Darktrace analyst Lucas O’Donohue for his insights on the above threat find.
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.
Why organizations are moving to label-free, behavioral DLP for outbound email
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
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.
Beyond MFA: Detecting Adversary-in-the-Middle Attacks and Phishing with Darktrace
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 / IDENTITYTMidentified 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.
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”.
Figure 2: Darkrace’s detection of an unusual surge in outbound emails containing suspicious content, shortly following the creation of a new email rule.
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.
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.
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)
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