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January 10, 2019

Insider Analysis of Emotet Malware

Uncover the secrets of Emotet with our latest Darktrace expert analysis. Learn how to identify and understand trojan horse attacks.
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
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10
Jan 2019

While both traditional security tools and the attacks against them continue to improve, advanced cyber-criminals are increasingly exploiting the weakness inherent to any organization’s security posture: its employees. Designed to mislead such employees into compromising their devices, computer trojans are now rapidly on the rise. In 2018, Darktrace detected a 239% year-on-year uptick in incidents related specifically to banking trojans, which use deception to harvest the credentials of online banking customers from infected machines. And one banking trojan in particular, Emotet, is among the costliest and most destructive malware variants currently imperilling governments and companies worldwide.

Emotet is a highly sophisticated malware with a modular architecture, installing its main component first before delivering additional payloads. Further increasing its subtlety is the fact that Emotet is considered to be ‘polymorphic malware’, since it constantly changes its identifiable features to evade detection by antivirus products. And, as will be subsequently discussed in greater detail, Emotet has advanced persistence techniques and worm-like self-propagation abilities, which render it uniquely resilient and dangerous.

Since its launch in 2014, Emotet has been adapted and repurposed on numerous occasions as its targets have diversified. Initially, Emotet’s primary victims were German banks, from which the malware was designed to steal financial information by intercepting network traffic. By this past year’s end, Emotet had spread far and wide while shifting focus to U.S. targets, resulting in permanently lost files, costly business interruptions, and serious reputational harm.

How Emotet works

(Image courtesy of US-CERT)

Emotet is spread by targeting Windows-based systems via sophisticated phishing campaigns, employing social engineering techniques to fool users into believing that the malware-laden emails are legitimate. For instance, the latest versions of Emotet were delivered by way of Thanksgiving-related emails, which invited their American recipients to open an apparently innocuous Thanksgiving card:

These emails contain Microsoft Word documents that are either linked or attached directly. The Word files, in turn, act as vectors for malicious macros, which must be explicitly enabled by the user to be executed. For security reasons, running macros by default is disabled in most of the latest Microsoft application versions, meaning that the cyber-criminals responsible must resort to tricking users in order to enable them — in this case, by enticing them with the Thanksgiving card.

Once the macros are enabled, the Word file is executed and a PowerShell command is activated to retrieve the main Emotet component from compromised servers. The trojan payload is then downloaded and executed into the victim’s system. As mentioned above, Emotet payloads are polymorphic, often allowing them to slip past conventional security tools undetected.

How Emotet persists and propagates

Once Emotet has been executed on the victim’s device, it begins deploying itself with two main objectives: (1) achieving persistence and (2) spreading to more machines. To achieve the first aim, which involves resisting a reboot and various attempts at removal, Emotet does the following:

  • Creates scheduled tasks and registry key entries, ensuring its automatic execution during every system start-up.
  • Registers itself by creating files that have randomly generated names in system root directories, which are run as Windows services.
  • Typically stores payloads in paths located off AppData\Local and AppData\Roaming directories that it masks with names that appear legitimate, such as ‘flashplayer.exe’.

Emotet’s second key goal is that of spreading across local networks and beyond in order to infect as many machines as possible. To this end, Emotet first gathers information on both the victim’s system itself and the operating system it uses. Following this reconnaissance stage, it establishes encrypted command and control communications (C2) with its parent infrastructure before determining which payloads it will deliver. After reporting a new infection, Emotet downloads modules from the C2 servers, including:

  • WebBrowserPassView: A tool that steals passwords from most common web browsers like Chrome, Safari, Firefox and Internet Explorer.
  • NetPass.exe: A legitimate tool that recovers all the network passwords stored on the system for the current logged-on user.
  • MailPassView: A tool that reveals passwords and account details for popular email clients, such as Hotmail, Gmail, Microsoft Outlook, and Yahoo! Mail.
  • Outlook PST scraper: A module that searches Outlook’s messages to obtain names and email addresses from the victim’s Outlook account.
  • Credential enumerator: A module that enumerates network resources and attempts to gain access to other machines via SMB enumeration and brute-forcing connections.
  • Banking trojans: These include Dridex, IceID, Zeus Panda, Trickbot and Qakbot, all of which harvest banking account information via browser monitoring routines.

Whilst the WebBrowserPassView, NetPass.exe and MailPassView modules are able to steal the compromised user’s credentials, the PST scraper module can ransack the user’s contact list of friends, family members, colleagues and clients, enabling Emotet to self-propagate by sending phishing emails to those contacts. And because such emails are sent from the hijacked accounts of known acquaintances and loved ones, their recipients are more likely to open their infected attachments and links.

Emotet’s other self-propagation method is via brute-forcing credentials using various password lists, with the intent of gaining access to other machines within the network. When unsuccessful, the malware’s repeated failed login attempts can cause users to become locked out of their accounts, and when successful, the victims may become infected without even clicking on a malicious link or attachment. These tactics have collectively made Emotet remarkably durable and widespread. Indeed, in line with Darktrace’s discovery that incidents related to banking trojans have increased by 239% from 2017 to 2018, Emotet alone recorded a 39% increase, and the worst may be yet to come.

How AI fights back

Emotet presents significant challenges for traditional security tools, both because it exploits the ubiquitous vulnerability of human error, and because it is designed specifically to bypass endpoint solutions. Yet unlike such traditional tools, Darktrace leverages unsupervised machine learning algorithms to detect cyber-threats that have already infiltrated the network. Modelled after the human immune system, Darktrace AI works by learning the individual ‘pattern of life’ of every user, device, and network that it safeguards. From this ever-evolving sense of ‘self,’ Darktrace can differentiate between normal and anomalous behavior, allowing it to identify cyber-attacks in much the same way that our immune system spots harmful germs.

Recently, Darktrace’s AI models managed to detect a machine on a clients’ network that was experiencing active signs of an Emotet infection. The device was observed downloading a suspicious file and, shortly thereafter, began beaconing to a rare external destination, likely reporting the infection to a C2 server.

The device was then observed moving laterally across the network by performing brute force activities. In fact, Darktrace detected thousands of Kerberos failed logins, including to administrative accounts, as well as multiple SMB session failures that used a range of common usernames, such as ‘admin’ and ‘exchange’. Below is a graph showing the SMB and Kerberos brute-force activity on the breached device:

In addition to the brute-forcing activity performed by the credential enumerator module, Darktrace also detected another payload that was potentially functioning as an email spammer. The infected machine started to make a high number of outgoing connections over common email ports. This activity is consistent with Emotet’s typical spreading behavior, which revolves around sending emails to the victim’s hijacked email contacts. Below is an image of Darktrace models breached during the reported Emotet infection:

By forming a comprehensive understanding of normalcy, Darktrace can flag even the most minute anomalies in real time, thwarting subtle threats like Emotet that have already circumvented the network perimeter. To counter such advanced banking trojans, cyber AI defenses like Darktrace have become an organizational necessity.

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

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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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About the author
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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