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August 25, 2020

Emotet Resurgence: Email & Network Defense Insights

Explore how Darktrace's defense in depth strategy combats Emotet's resurgence in email and network layers, ensuring robust cybersecurity.
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
Written by
Dan Fein
VP, Product
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25
Aug 2020

The Emotet banking malware first emerged in 2014, and has since undergone multiple iterations. Emotet seeks to financially profit from a range of organizations by spreading rapidly from device to device and stealing sensitive financial information.

Darktrace’s AI has detected the return of this botnet after a five month absence. The new Spamware campaign has hit multiple industries through highly sophisticated phishing emails, containing either URLs linking to the download of a macro-containing Microsoft Word document or an attachment of the document itself. This iteration uses new variants of infrastructure and malware that were unknown to threat intelligence lists – thus easily bypassing static, rule-based defenses.

In this blog post, we investigate the attack from two angles. The first documents a case where Emotet successfully infiltrated a company’s network, where it was promptly detected and alerted on by the Enterprise Immune System. We then explore two customers who had extended Darktrace’s Cyber AI coverage to the inbox. While these organizations were also targeted by this latest Emotet campaign, the malicious email containing the Emotet payload was identified and blocked by Antigena Email.

Case study one: Detecting Emotet in the network

Figure 1: A timeline of the attack

This first case study looks at a large European organization spanning multiple industries, including healthcare, pharmaceuticals, and manufacturing. Darktrace’s AI was monitoring over 2500 devices when the organization became a victim of this new wave of Emotet.

The attack entered the business via a phishing email that fell outside of Darktrace’s scope in this particular deployment, as the customer had not yet activated Antigena Email. Either a malicious link or a macro-embedded Word document in the email directed a device to the malicious payload.

Darktrace’s Enterprise Immune System witnessed SSL connections to a 100% rare external IP address, and detected a Kernel crash on the device shortly afterwards, indicating potential exploitation.

Following these actions, the desktop began to beacon to multiple external endpoints using self-signed or invalid SSL certificates. The observed endpoints had previously been associated with Trickbot C2 servers and the Emotet malware. The likely overall dwell time – that is the length of time an attacker has free reign in an environment before they are eradicated – was in this instance around 24 hours, with most of the activity taking place on July 23.

The device then made a large number of new and unusual internal connection attempts over SMB (port 445) to 97 internal devices during a one-hour period. The goal was likely lateral movement, possibly with the intention to infect other devices, download additional malware, and send out more spam emails.

Darktrace’s AI had promptly alerted the security team to the initial rare connections, but when the device attempted lateral movement it escalated the severity of the alert. The security team was able to remediate the situation before further damage was done, taking the desktop offline.

This overview of the infected device shows the extent of the anomalous behavior, with over a dozen Darktrace detections firing in quick succession.

Figure 2: A graph showing unusual activity in combination with the large number of model breaches on July 23

Figure 3: A list of all model breaches occurring over a small time on the compromised device

Case study two: Catching Emotet in the email environment

While Darktrace’s Enterprise Immune System allows us to visualize the attack within the network, Antigena Email has also identified the Emotet phishing campaign in many other customer environments and stopped the attack before the payload could be downloaded.

One European organization was hit by multiple phishing emails associated with Emotet. These emails use a number of tactics, including personalized subject lines, malicious attachments, and hidden malicious URLs. However, Darktrace’s AI recognized the emails as highly anomalous for the organization and prevented them from reaching employees’ inboxes.

Figure 4: A snapshot of Antigena Email’s user interface. The subject line reads ‘Notice of transfer.’

Despite claiming to be from CaixaBank, a Spanish financial services company, Antigena Email revealed that the email was actually sent from a Brazilian domain. The email also contained a link that was hidden behind text suggesting it would lead to a CaixaBank domain, but Darktrace recognized this as a deliberate attempt to mislead the recipient. Antigena Email is unique in its ability to gather insights from across the broader business, and it leveraged this ability to reveal that the link in fact led to a WordPress domain that Darktrace’s AI identified as 100% rare for the business. This would not have been possible without a unified security platform analyzing and comparing data across different parts of the organization.

Figure 5: The malicious links contained in the email

The three above links surfaced by Darktrace are all associated with the Emotet malware, and prompt the user to download a Word file. This document contains a macro with instructions for downloading the actual virus payload.

Another email targeting the same organization contained a header suggesting it was from Vietnam. The sender had never been in any previous correspondence across the business, and the single, isolated link within the email was also revealed to be a 100% rare domain. The website displayed when visiting the domain imitates a legitimate printing business, but appears hastily made and contained a similar malicious payload.

In both cases, Darktrace’s AI recognized these as phishing attempts due to its understanding of normal communication patterns and behavior for the business and held the emails back from the inbox, preventing Emotet from entering the next phase of the attack life cycle.

Case study three: A truly global campaign

Darktrace has seen Emotet in attacks targeting customers around the world, with one of the most recent campaigns aimed at a food production and distribution company in Japan. This customer received six Emotet emails across July 29 and July 30. The senders spoofed Japanese names and some existing Japanese companies, including Mitsubishi. Antigena Email successfully detected and actioned these emails, recognizing the spoofing indicators, ‘unspoofing’ the emails, and converting the attachments.

Figure 6: A second Emotet email targeting an organization in Japan

Revealing a phish

Both the subject line and the filename translate to “Regarding the invoice,” followed by a number and the date. The email imitated a well-known Japanese company (三菱食品(株)), with ‘藤沢 昭彦’ as a common Japanese name and the appended ‘様’ serving a similar function to ‘Sir’ or ‘Dr,’ in a clear attempt to mimic a legitimate business email.

A subsequent investigation revealed that the sender’s location was actually Portugal, and the hash values of Microsoft Word attachments were consistent with Emotet. Crucially, at the time of the attack, these file hashes were not publicly associated with any malicious behavior and so could not have been used for initial detection.

Figure 7: Antigena Email shows critical metrics revealing the true source of the email

Surfacing further key metrics behind the email, Antigena Email revealed that the true sender was using a GMO domain name. GMO is a Japanese cloud-hosting company that offers cheap web email services.

Figure 8: Antigena Email reveals the anomalous extensions and mimes

The details of the attachment show that both the extension and mime type is anomalous in comparison to documents this customer commonly exchanges by email.

Figure 9: Antigena Email detects the attempt at inducement

Antigena Email’s models are able to recognize topic anomalies and inducement attempts in emails, regardless of the language they are written in. Despite this email being written in Japanese, Darktrace’s AI was still able to reveal the attempt at inducement, giving the email a high score of 85.

Figure 10: The six successive Emotet emails

The close proximity in which these emails were sent and the fact they all contained URLs consistent with Emotet suggests that they are likely part of the same campaign. Different recipients received the emails from different senders in an attempt to bypass traditional security tools, which are trained to deny-list an individual sender once it is recognized as bad.

A defense in depth

This new campaign and the comeback of the Emotet malware has shown the need for defense in depth – or having multiple layers of security across the different areas of a business, including email, network, cloud and SaaS, and beyond.

Historically, defense in depth has led companies to adopt myriad point solutions, which can be both expensive and challenging to manage. Security leaders are increasingly abandoning point solutions in favor of a single security platform, which not only makes handling the security stack easier and more efficient, but creates synergies between different parts of the platform. Data can be analyzed across different sources and insights drawn from different areas of the organization, helping detect sophisticated attacks that might attempt to exploit a business’ siloed approach to security.

A single platform ultimately reduces the friction for security teams while allowing for effective, company-wide incident investigation. And when a platform approach leverages AI to understand normal behavior rather than looking for ‘known bad’, it can detect unknown and emerging threats – and help prevent damage from being done.

Thanks to Darktrace analyst Beverly McCann for her insights on the above threat find.

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
Written by
Dan Fein
VP, Product

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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

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

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About the author
David Ison
Cyber Analyst
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