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August 26, 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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26
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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August 5, 2026

Testing a Prompt injection Attack Against an Enterprise AI Agent

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Key takeaways

  • Darktrace successfully detected and quarantined a prompt injection email before it could be processed by an enterprise AI agent.  
  • Prompt injection attacks increasingly rely on natural language rather than traditional malware, making behavioral analysis an important complement to signature-based detection.  
  • Organizations deploying AI agents should combine model guardrails with behavioral monitoring to reduce the risk of malicious instructions reaching enterprise systems.

How behavioral detection helps stop prompt injection attacks

A Darktrace customer running a Gemini AI agent in Google Cloud asked us two simple questions:

“If my agent can read inbound emails and access internal data, what stops an attacker from hiding malicious instructions in the message? Couldn’t the agent be tricked into deleting or exfiltrating sensitive data?”

The scenario centers on an indirect prompt injection attack, where malicious instructions are hidden inside content that an AI model later interprets as trusted input. The same weakness was exposed by  EchoLeak (CVE-2025-32711), a zero-click Microsoft 365 Copilot vulnerability enabled data exfiltration from a single well-crafted email..

This blog follows the Darktrace team’s investigation of the customer’s hypothesis and examines how the attack interacted with their existing security stack. The results highlight which defenses held, where gaps emerged, and how behavioral detection mattered more than guardrails. This investigation also demonstrates why behavioral detection is becoming increasingly important for AI security, as prompt injections often contain no traditional indicators of compromise.  

How do prompt injection attacks work?

Prompt injection works by carefully crafting the content and structure of the prompt to alter the LLM’s behavior or output in unintended ways. This can cause models to violate guardrails, generate harmful content or enable unauthorised access.

Prompt injection attack example

The well-known example, EchoLeak (CVE-2025-32711), was a zero-click vulnerability in Microsoft 365 Copilot that relied on a carefully crafted email containing hidden instructions that the AI system interpreted as commands rather than content, creating a pathway for unauthorized access to sensitive information without any user interaction.

While Darktrace / SECURE AI is designed to prevent agents from producing unintended outcomes, we wanted to see if we could catch and prevent this threat type earlier in the attack life-cycle, at the email security layer.

How we tested prompt injection attacks on an enterprise agent

Summary:

  1. Claude generated a prompt injection payload.  
  2. Hidden instructions were embedded in an email.  
  3. The email passed traditional validation checks.  
  4. Darktrace analyzed the language and sender behavior.  
  5. The email was quarantined before the AI agent could process it.

To test Darktrace / EMAIL against this attack class, we opened Claude, gave it the customer's context and problem statement (Gemini agent with inbox access, internal tool calls), told it we were validating Darktrace / EMAIL's detection of prompt injections, and asked for a test payload. See below:

Figure 1
Figure 2

Despite the guardrails supposedly built into the model, Claude surprisingly gave us the entire exploit in plaintext (albeit very basic), illegible to a human as the text was sent in white text (see Figure 1) but framed as an authoritative override for anything downstream reading the mail programmatically (i.e. the Gemini agent).

How Darktrace detected a prompt injection attack

We then sent the Claude-crafted email from a freemail address to the target recipient’s inbox. Despite the email containing no malicious payload, the freemail address having no malicious reputation, and the validation checks all passing, Darktrace  /EMAIL flagged the email as a 93/100 anomaly and moved it to junk, out of scope for the AI agent.

Figure 3: The test email sent with the hidden prompt injection
Figure 4: The email analysis in Darktrace / EMAIL 
Figure 5: Darktrace / EMAIL detection of malicious activity

The interesting part is what triggered the detection (see Figure 5)

  • Possible machine prompt content: text in the body detected as instructions written for a machine to execute, not for a human to read
  • Possible machine prompt content + basic suspicious correspondence: the same content, correlated with sender-side anomalies: freemail domain (yahoo[.]com), unknown correspondent, no prior mail history with the recipient, and suspicious references to payment information

Neither of those is a signature match. Nothing in the email was on a blacklist. There was no malware, no link and no attachment. Darktrace analyzed the context in which the email was delivered and flagged it as likely risky.  The anomalous language features and the context of the sender relative to the recipient's normal behavior, combined with the unusual hidden text (prompt) were enough for Darktrace / EMAIL to act on the risk.

Result: Darktrace / EMAIL autonomously junked the email, out of scope for any AI agent parsing the inbox.

Why behavioral security makes a difference detecting prompt injection attacks

Cyberattacks don't look like traditional exploits anymore. They now operate in natural language, not strictly code.

That breaks the traditional stack. AV, firewalls, static scanning and signature-based SEGs all assume a payload to inspect.  

A prompt injection has no payload. It's just an instruction, written in natural language, dressed up as anything the attacker wants: an invoice, an HR request, a calendar invite, some simple PowerPoint slides.

EchoLeak proved that hidden instructions can sit inside an email invisible to the user but fully readable by the LLM, and the LLM will follow them blindly.  

This test and GTG-1002 proved that the LLM itself can be socially engineered. Tell it you're an authorized tester and it will hand you the attack.

Rules and static classifiers can catch the obvious cases. But natural language has infinite variants, and the attack surface is the model's innate functionality to comply.  

The deeper problem here is intent: an LLM can't reliably tell whether an instruction in its context came from its developer, its user, or an attacker who slipped it into an email. To the LLM, everything reads as language and looks like a legitimate ask. This is why behavioural detection wins, as you become aware of intent when you look at the context of an interaction. Does this sender normally send this kind of message to this recipient? Does this prompt fit the user's normal pattern? Is this agent behaving the way this agent normally behaves?  

Intent can't be read off a single email, it emerges from behavioral context. Which is how Darktrace enables threat detection, through behavioral understanding.

Why enterprise AI security requires more than guardrails

Claude didn't roll over immediately… the first section of the response was a (slight) pushback, but then it wrote the payload anyway without having to ask twice.

Here the framing of the prompt did all the work. The “testing security capabilities” angle moved the model from refusal to unquestioned compliance to the user prompt.

This isn't the first time this has happened, of course. Anthropic disclosed in November 2025 that a Chinese state-sponsored group they tracked as GTG-1002 ran the first documented AI-orchestrated espionage campaign against ~30 targets by posing as employees of a legitimate cybersecurity firm doing authorised penetration testing.

The takeaway isn't that AI guardrails are ineffective. They raise the cost of low-effort attacks and remain an important first layer of defense. However, for most organizations today, they’re the only line of defense when deploying AI agents. If a prompt injection bypasses those controls, organizations still need a way to detect and stop malicious behavior elsewhere in the attack chain.

Attackers will continue to have working prompt injections easily and quickly. The question is what stops one when it lands in an inbox your agent is reading.

That's where behavioral detection comes in.

How Darktrace detects prompt injection attacks in emails

Two things Darktrace does that a model-level guardrail or static rules and signatures can't:

Natural language analysis at the email or prompt layer. The email is assessed on its own merits: is this content shaped like instructions for a machine, regardless of what the receiving agent decides to do about it?

Behavioral context around the language. An AI agent behaves like an extremely agreeable human, and it will go above and beyond to comply with the user’s request. That's exactly why you must consider the business context, such sender behaviour, mailing history, and organisational norms, as these matter even more when the recipient is an AI.

Darktrace has been perfecting behavioral anomaly detection for over a decade; the same self-learning approach that catches BEC and account takeover applies directly to prompt injection delivery. Our multi-layered AI stack extracts content from the message, builds behavioural understanding through social graphing and Pattern of Life analysis, and then combines natural language, topic, inducement, sender relationship and anomaly signals before deciding what action to take.  

This matters for prompt injection because the threat is not the plain language itself, but the intent behind the language that can cause an AI agent to respond in unexpected ways.

How to secure enterprise AI operations from prompt injection attacks

Email was the entry point in this case, but it is only one of many possible vectors.  

Anywhere an agent can retrieve information, an attacker can potentially introduce a prompt injection.

Emails, documents, SharePoint sites, web pages, knowledge bases, chat platforms, and third-party integrations all provide opportunities to influence an agent's behavior. Wherever an agent finds its orders, a prompt injection opportunity exists.

This is why securing AI requires more than blocking malicious inputs. Organizations also need visibility into how agents behave after consuming information from across their environment. If an agent begins accessing unexpected data, taking unusual actions, or operating outside its normal patterns, those behaviors may provide the strongest signal that something has gone wrong.

Effective AI security requires defense in depth: reducing the likelihood of malicious instructions reaching the agent while maintaining the ability to detect and investigate suspicious behavior if they do.

The challenge isn't protecting a single entry point. It's recognizing that, in an AI-powered environment, every source of information is also a potential source of influence.

Are you deploying autonomous agents across your enterprise and want to see this tested in your environment? Let's talk.

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Carlo Loregian
Solutions Engineer

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August 4, 2026

Extending AI Security Visibility with Darktrace and Microsoft Agent 365

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AI agents are rapidly becoming embedded in everyday business operations, helping employees automate workflows, access information, and accelerate decision-making. As organizations embrace agentic AI, security teams face a growing challenge: understanding how AI is being used, what agents can access, and where risk may emerge.

As agents take on more business-critical work, security teams often need to move across multiple portals to understand risks spanning identity, data, and threat activity. This fragmented view can make it difficult to assess an agent's overall risk posture and determine where attention is needed. Organizations need a way to bring these signals together without disrupting existing security investments or workflows.

Today, Darktrace is announcing an integration between Darktrace / SECURE AI and Microsoft Agent 365 that brings Darktrace's Adaptive AI-driven risk signals directly into the Microsoft 365 Admin Center. By extending the visibility and risk understanding provided by Darktrace / SECURE AI into the Microsoft ecosystem, organizations can gain a more unified understanding of AI agent risk across their environments.

As one of the first security companies to partner with Microsoft to contribute third-party risk signals to the Agent Registry, Darktrace is helping shape how organizations understand and manage AI agent risk.

Extending visibility into the Microsoft Agent 365 experience

Microsoft Agent 365 provides administrators with a centralized registry of AI agents operating within their environment. As organizations expand their use of AI agents, this centralized visibility becomes increasingly important for governance and oversight.

This new integration extends that visibility by allowing Darktrace-generated risk signals to be surfaced directly within the Microsoft Agent 365 experience. By combining Microsoft's agent management and security capabilities with Darktrace's AI-powered risk analysis, organizations gain greater awareness of potential security concerns associated with AI agents operating across their environments.

By integrating Darktrace telemetry into Agent 365, customers can:  

  • Surface Darktrace-detected risks and signals alongside Microsoft-native signals in a single interface
  • Identify potentially compromised or anomalous AI agents more quickly
  • Gain unified understanding of context and agent behavior  

This approach reinforces a single control plane for AI security while allowing organizations to continue leveraging existing investments across both platforms.  

Why unified visibility of AI agent risk signals matters

As AI adoption accelerates across Microsoft environments, organizations must manage new forms of behavior, access patterns, and risk. Security teams need more than inventories and permissions. They need visibility into how AI systems operate and how risk evolves over time.  

This integration addresses a critical gap: how to bring behavioral AI security insights into the same control plane as identity, access, and agent management.  

With Darktrace and Microsoft Agent 365 together, organizations benefit from:  

  • Unified visibility: A single pane of glass for understanding AI agent risk signals across Microsoft and Darktrace signals  
  • Faster detection of abnormal agent behavior: Darktrace's Adaptive AI highlights deviations that may not be captured by static controls  
  • Operational efficiency: Security teams can triage and prioritize risk signals without switching between systems
  • Stronger trust in AI deployments: Clear attribution, context, and investigation pathways improve confidence in AI agent usage

Extending Microsoft's AI security model, not replacing it

Securing AI requires a layered approach that combines governance, visibility, threat detection, and risk management. This integration is designed to complement Microsoft's security capabilities, not duplicate them.  

Through Darktrace / SECURE AI, Darktrace contributes:  

  • Identification of risk via advanced prompt analysis  
  • Behavioral anomaly detection across AI agents  
  • Cross-environment threat correlation  
  • Autonomous insight into emerging or unknown risks  

Microsoft provides:  

  • Centralized agent management
  • Identity and access governance
  • Native detection of risk signals and enforcement capabilities

Together, these capabilities create a more complete, layered approach to securing AI-driven enterprises. Organizations gain the governance and policy controls needed to manage AI adoption while benefiting from continuous visibility into how AI is used across the business.

Building the future of secure AI

As AI agents become more deeply embedded in business processes, organizations need more than inventories and static controls. They need to understand how AI is being used, how agents behave, and where risk is emerging across the enterprise.

Darktrace / SECURE AI delivers that understanding through continuous visibility into AI activity, helping security teams assess intent, identify behavioral drift, and uncover emerging risk across both human and agent-driven workflows. Powered by Adaptive AI, it provides the context needed to secure AI as it evolves.  

The integration with Microsoft Agent 365 extends those insights into the workflows organizations already use. Agent 365 provides a unified control plane for governing and securing AI agents, while Darktrace contributes complementary behavioral risk signals that can be surfaced within the Agent 365 experience. Together, they give customers broader context on agent activity and risk while preserving the value of their existing Microsoft and Darktrace investments.

As enterprises move from AI experimentation to AI-powered execution, Microsoft and Darktrace help bring together governance, compliance, behavioral understanding, and oversight in a unified approach to AI security. For organizations adopting Microsoft 365 E7, Darktrace / SECURE AI further strengthens that foundation by providing continuous visibility into AI activity, agent behavior, and emerging risk as AI adoption scales.

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