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December 8, 2017

Darktrace: Investigating Widespread Trojan Infections

Discover how Darktrace expedites the investigation of widespread Trojan infections, enhancing cybersecurity and response times.
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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08
Dec 2017

This blog post outlines how Darktrace helps security operations centre (SOC) teams become more efficient by drastically cutting down the time needed to investigate incidents. This is illustrated by an example encountered in a recent Proof of Value where over 350 client devices had been infected by a stealthy banking trojan.

Identifying and investigating a compromise of this size would usually take a SOC team several hours if not days using disparate traditional security tools. Employing Darktrace, the most important questions were answered within 90 minutes. The main reason for this is that Darktrace provides full visibility and context into network activity for all devices monitored on a single, unified platform.

Alert fatigue & the cyber security skill gap

Getting cyber security right is difficult and time-consuming. Complexity is one of the main challenges the cyber security community is facing. These days, networks are only vaguely defined with digital supply chains, outsourcing, the push into the cloud and the advent of micro-virtualisation like Docker. The amount of data stored, devices connected to internal networks, connections made by devices and the heterogeneity in IT adds to this complexity. Managing it is difficult at best and securing it with traditional tools can be a daunting task.

Our industry is struggling with what has been labelled the ‘cyber security skill gap’. The demand for skilled, experienced security practitioners consistently outstrips supply. SOC teams struggle to find the right people for the job and to keep their analysts motivated in the face of a rapidly evolving threat landscape. Alert fatigue and burnout are common symptoms for SOC analysts working long hours and graveyard shifts.

Investigation methodology

Any incident responder will always begin by asking some high-level questions concerning the incident under investigation – regardless of it being an adware infection, a banking trojan, ransomware, an active intrusion or any other form of cyber security incident.

The most important questions usually are:

  • How did the infection occur? (To prevent the same initial infection vector in the future)
  • What behavior is the infected device exhibiting? (To understand the threat and the risk of the infection)
  • What Indicators of Compromise (IoC) are seen? (To update other security tools and to use for further investigation)
  • Are other devices infected as well? (To assess the extent of the infection)

We did a recent Proof of Value with an IT service provider in EMEA. Darktrace entered an environment which had already succumbed to a widespread compromise – over 350 client devices had been infected with banking trojans. Let’s walk through how we identified, triaged and investigated this infection using Darktrace.

Identifying the incident

Darktrace came into the environment after the initial infection had taken place already. Darktrace instantly identified several devices exhibiting unexpected HTTP beaconing to unusual, rare external IP addresses. The devices made HTTP POST requests without prior GET requests along other suspicious behavior. Darktrace created several high-severity alerts for this, e.g. ‘Compromise / Suspicious HTTP Beacons to Dotted Quad’ and ‘Compromise / Possible Malware HTTP Comms’:

Figure 1: Example Darktrace alert.

Triaging the incident

Darktrace then provides context around this alert - e.g. the external IP the beaconing was made to, the internal device including the associated user, and the suspicious behavior:

Figure 2: Detection context and C2 IP.

A quick investigation of the external IP reveals that it is a recently discovered command and control (C2) IP address for the Dridex banking trojan.

Drilling deeper into this, Darktrace provides PCAPs for every connection seen. A PCAP for the C2 connection above confirms this incident as active, successful, encoded beaconing to a malicious C2 IP:

Figure 3: PCAP and encoded HTTP POSTs.

Investigating the incident

At this stage, we want to further examine the behavior of the infected device around the time of the incident. Darktrace provides full visibility into past activity, including all network connection made by any device - regardless of whether the incident occurred on the device or not.

We attend to all external connections made by the infected device around the time of the incident and immediately identify more suspicious C2 communication:

Figure 4: More device behavior; further C2 IPs.

By now we have identified 6 different C2 IP addresses.

We can use Darktrace’s ‘External Sites Summary’ to view all devices that have connected to a specific IP or domain in the recent past. Doing this for the initial C2 IP yields the following result (excerpt):

Figure 5: External Sites Summary; further infections.

We immediately identify 5 additional devices that made successful connections to the C2 IP address. In fact, the list above is abridged as we actually saw over 350 devices connecting to this and other C2 IP addresses. Notably, all observed devices appear to have a similar naming structure - this will become important in the next part of the analysis.

At this point we have answered all but the first question: ‘How did the infection occur?’

Darktrace started monitoring the network after the initial infection occurred and spread. Further research into the C2 IP addresses shows that they are associated with the Emotet trojan. This sophisticated malware often precedes banking trojan (e.g. Dridex) infections and is spread via phishing. We can thus assume that phishing was a likely initial infection vector.

How then did the infection manage to spread to so many devices?

Surely not all users clicked on suspicious phishing emails? Recent versions of Emotet have limited lateral movement capabilities. They mainly propagate via SMB brute forcing - trying administrative accounts and hard-coded password lists. The naming convention on the infected devices is very similar - this could indicate a similar build-process and setup of the devices. If a vulnerability - such as an administrative account with a weak password - existed on one of the devices, it might be present in all of the devices with a similar build.

Using Darktrace, the security team has now a solid understanding of the nature and size of the infection, the IoCs available to update firewalls and other preventive security controls and outstanding remediation-activities.

What would this investigation look like with traditional tools, not using Darktrace?

Detecting these covert banking trojans in the first place, let alone triaging them fully, can be a difficult challenge in itself. Current banking Trojan strains such as Dridex, Fedeo or Vawtrak keep updating the malware with new C2 addresses to avoid blacklisting. Initial detection could be at any stage of the attack lifecycle – likely it will be in the latter stages though, when considerable damage has already been done.

An analyst will have to log into various security devices to get close to the same level of visibility provided in Darktrace – web proxy logs, anti-virus logs, running PCAPs on infected hosts, SIEM logs. Having to switch between all those disparate security tools is not time-efficient and produces a fragmentary picture of what actually transpired.

Conclusion

A working hypothesis is that a single device was initially infected via phishing, allowing Emotet to spread to over 350 internal devices via SMB brute forcing. It took no longer than 90 minutes to come from an initial detection of the incident to this conclusion, which forms the basis for an actionable report.

The last thing a SOC needs is yet another tool producing a profusion of alerts. Using Darktrace’s machine learning and unrivalled network visibility, you can focus on the small set of relevant alerts and rapidly investigate those incidents according to their severity and priority.

Darktrace can reduce costs even if you bring in a third-party incident response team. You will be able to significantly speed up their ongoing investigation if they have access to Darktrace. Third-party incident response teams are expensive – their daily rates ranging between £2,000 and £3,000 per day. Cutting their work down from days to hours will result in cost and efforts saved.

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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