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July 30, 2025

Darktrace's Cyber AI Analyst in Action: 4 Real-World Investigations into Advanced Threat Actors

As AI reshapes the cybersecurity landscape, Darktrace’s Cyber AI Analyst automates early-stage investigations, mimicking human reasoning to detect and respond to threats at machine speed. This blog explores four real-world cases where it identified sophisticated threat actors, including nation-state adversaries.
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
Nathaniel Jones
SVP, Global Threat Intelligence
Man looking at computer doing work, cybersecurity, AI, AI analystDefault blog image
30
Jul 2025

From automation to intelligence

There’s a lot of attention around AI in cybersecurity right now, similar to how important automation felt about 15 years ago. But this time, the scale and speed of change feel different.

In the context of cybersecurity investigations, the application of AI can significantly enhance an organization's ability to detect, respond to, and recover from incidents. It enables a more proactive approach to cybersecurity, ensuring a swift and effective response to potential threats.

At Darktrace, we’ve learned that no single AI technique can solve cybersecurity on its own. We employ a multi-layered AI approach, strategically integrating a diverse set of techniques both sequentially and hierarchically. This layered architecture allows us to deliver proactive, adaptive defense tailored to each organization’s unique environment.

Darktrace uses a range of AI techniques to perform in-depth analysis and investigation of anomalies identified by lower-level alerts, in particular automating Levels 1 and 2 of the Security Operations Centre (SOC) team’s workflow. This saves teams time and resources by automating repetitive and time-consuming tasks carried out during investigation workflows. We call this core capability Cyber AI Analyst.

How Darktrace’s Cyber AITM Analyst works

Cyber AI Analyst mimics the way a human carries out a threat investigation: evaluating multiple hypotheses, analyzing logs for involved assets, and correlating findings across multiple domains. It will then generate an alert with full technical details, pulling relevant findings into a single pane of glass to track the entire attack chain.

Learn more about how Cyber AI Analyst accomplishes this here:

This blog will highlight four examples where Darktrace’s agentic AI, Cyber AI Analyst, successfully identified the activity of sophisticated threat actors, including nation state adversaries. The final example will include step-by-step details of the investigations conducted by Cyber AI Analyst.

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Case 1: Cyber AI Analyst vs. ShadowPad Malware: East Asian Advanced Persistent Threat (APT)

In March 2025, Darktrace detailed a lengthy investigation into two separate threads of likely state-linked intrusion activity in a customer network, showcasing Cyber AI Analyst’s ability to identify different activity threads and piece them together.

The first of these threads...

occurred in July 2024 and involved a malicious actor establishing a foothold in the customer’s virtual private network (VPN) environment, likely via the exploitation of an information disclosure vulnerability (CVE-2024-24919) affecting Check Point Security Gateway devices.

Using compromised service account credentials, the actor then moved laterally across the network via RDP and SMB, with files related to the modular backdoor ShadowPad being delivered to targeted internal systems. Targeted systems went on to communicate with a C2 server via both HTTPS connections and DNS tunnelling.

The second thread of activity...

Which occurred several months earlier in October 2024, involved a malicious actor infiltrating the customer's desktop environment via SMB and WMI.

The actor used these compromised desktops to discriminately collect sensitive data from a network share before exfiltrating such data to a web of likely compromised websites.

For each of these threads of activity, Cyber AI Analyst was able to identify and piece together the relevant intrusion steps by hypothesizing, analyzing, and then generating a singular view of the full attack chain.

Cyber AI Analyst identifying and piecing together the various steps of the ShadowPad intrusion activity.
Figure 1: Cyber AI Analyst identifying and piecing together the various steps of the ShadowPad intrusion activity.
Cyber AI Analyst Incident identifying and piecing together the various steps of the data theft activity.
Figure 2: Cyber AI Analyst Incident identifying and piecing together the various steps of the data theft activity.

These Cyber AI Analyst investigations enabled a quicker understanding of the threat actor’s sequence of events and, in some cases, led to faster containment.

Read the full detailed blog on Darktrace’s ShadowPad investigation here!

Case 2: Cyber AI Analyst vs. Blind Eagle: South American APT

Since 2018, APT-C-36, also known as Blind Eagle, has been observed performing cyber-attacks targeting various sectors across multiple countries in Latin America, with a particular focus on Colombia.

In February 2025, Cyber AI Analyst provided strong coverage of a Blind Eagle intrusion targeting a South America-based public transport provider, identifying and correlating various stages of the attack, including tooling.

Cyber AI Analyst investigation linking likely Remcos C2 traffic, a suspicious file download, and eventual data exfiltration.Type image caption here (optional)
Figure 3: Cyber AI Analyst investigation linking likely Remcos C2 traffic, a suspicious file download, and eventual data exfiltration.Type image caption here (optional)
Cyber AI Analyst identifying unusual data uploads to another likely Remcos C2 endpoint and correlated each of the individual detections involved in this compromise, identifying them as part of a broader incident that encompassed C2 connectivity, suspicious downloads, and external data transfers.
Figure 4: Cyber AI Analyst identifying unusual data uploads to another likely Remcos C2 endpoint and correlated each of the individual detections involved in this compromise, identifying them as part of a broader incident that encompassed C2 connectivity, suspicious downloads, and external data transfers.

In this campaign, threat actors have been observed using phishing emails to deliver malicious URL links to targeted recipients, similar to the way threat actors have previously been observed exploiting CVE-2024-43451, a vulnerability in Microsoft Windows that allows the disclosure of a user’s NTLMv2 password hash upon minimal interaction with a malicious file [4].

In late February 2025, Darktrace observed activity assessed with medium confidence to be associated with Blind Eagle on the network of a customer in Colombia. Darktrace observed a device on the customer’s network being directed over HTTP to a rare external IP, namely 62[.]60[.]226[.]112, which had never previously been seen in this customer’s environment and was geolocated in Germany.

Read the full Blind Eagle threat story here!

Case 3: Cyber AI Analyst vs. Ransomware Gang

In mid-March 2025, a malicious actor gained access to a customer’s network through their VPN. Using the credential 'tfsservice', the actor conducted network reconnaissance, before leveraging the Zerologon vulnerability and the Directory Replication Service to obtain credentials for the high-privilege accounts, ‘_svc_generic’ and ‘administrator’.

The actor then abused these account credentials to pivot over RDP to internal servers, such as DCs. Targeted systems showed signs of using various tools, including the remote monitoring and management (RMM) tool AnyDesk, the proxy tool SystemBC, the data compression tool WinRAR, and the data transfer tool WinSCP.

The actor finally collected and exfiltrated several gigabytes of data to the cloud storage services, MEGA, Backblaze, and LimeWire, before returning to attempt ransomware detonation.

Figure 5: Cyber AI Analyst detailing its full investigation, linking 34 related Incident Events in a single pane of glass.

Cyber AI Analyst identified, analyzed, and reported on all corners of this attack, resulting in a threat tray made up of 34 Incident Events into a singular view of the attack chain.

Cyber AI Analyst identified activity associated with the following tactics across the MITRE attack chain:

  • Initial Access
  • Persistence
  • Privilege Escalation
  • Credential Access
  • Discovery
  • Lateral Movement
  • Execution
  • Command and Control
  • Exfiltration

Case 4: Cyber AI Analyst vs Ransomhub

Cyber AI Analyst presenting its full investigation into RansomHub, correlating 38 Incident Events.
Figure 6: Cyber AI Analyst presenting its full investigation into RansomHub, correlating 38 Incident Events.

A malicious actor appeared to have entered the customer’s network their VPN, using a likely attacker-controlled device named 'DESKTOP-QIDRDSI'. The actor then pivoted to other systems via RDP and distributed payloads over SMB.

Some systems targeted by the attacker went on to exfiltrate data to the likely ReliableSite Bare Metal server, 104.194.10[.]170, via HTTP POSTs over port 5000. Others executed RansomHub ransomware, as evidenced by their SMB-based distribution of ransom notes named 'README_b2a830.txt' and their addition of the extension '.b2a830' to the names of files in network shares.

Through its live investigation of this attack, Cyber AI Analyst created and reported on 38 Incident Events that formed part of a single, wider incident, providing a full picture of the threat actor’s behavior and tactics, techniques, and procedures (TTPs). It identified activity associated with the following tactics across the MITRE attack chain:

  • Execution
  • Discovery
  • Lateral Movement
  • Collection
  • Command and Control
  • Exfiltration
  • Impact (i.e., encryption)
Step-by-step details of one of the network scanning investigations performed by Cyber AI Analyst in response to an anomaly alerted by Darktrace.
Figure 7: Step-by-step details of one of the network scanning investigations performed by Cyber AI Analyst in response to an anomaly alerted by Darktrace.
Step-by-step details of one of the administrative connectivity investigations performed by Cyber AI Analyst in response to an anomaly alerted by Darktrace.
Figure 8: Step-by-step details of one of the administrative connectivity investigations performed by Cyber AI Analyst in response to an anomaly alerted by Darktrace.
 Step-by-step details of one of the external data transfer investigations performed by Cyber AI Analyst in response to an anomaly alerted by Darktrace. Step-by-step details of one of the external data transfer investigations performed by Cyber AI Analyst in response to an anomaly alerted by Darktrace.
Figure 9: Step-by-step details of one of the external data transfer investigations performed by Cyber AI Analyst in response to an anomaly alerted by Darktrace.
Step-by-step details of one of the data collection and exfiltration investigations performed by Cyber AI Analyst in response to an anomaly alerted by Darktrace.
Figure 10: Step-by-step details of one of the data collection and exfiltration investigations performed by Cyber AI Analyst in response to an anomaly alerted by Darktrace.
Step-by-step details of one of the ransomware encryption investigations performed by Cyber AI Analyst in response to an anomaly alerted by Darktrace.
Figure 11: Step-by-step details of one of the ransomware encryption investigations performed by Cyber AI Analyst in response to an anomaly alerted by Darktrace.

Conclusion

Security teams are challenged to keep up with a rapidly evolving cyber-threat landscape, now powered by AI in the hands of attackers, alongside the growing scope and complexity of digital infrastructure across the enterprise.

Traditional security methods, even those that use some simple machine learning, are no longer sufficient, as these tools cannot keep pace with all possible attack vectors or respond quickly enough machine-speed attacks, given their complexity compared to known and expected patterns. Security teams require a step up in their detection capabilities, leveraging machine learning to understand the environment, filter out the noise, and take action where threats are identified. This is where Cyber AI Analyst steps in to help.

Credit to Nathaniel Jones (VP, Security & AI Strategy, FCISO), Sam Lister (Security Researcher), Emma Foulger (Global Threat Research Operations Lead), and Ryan Traill (Analyst Content Lead)

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Learn more about Cyber AI Analyst

Discover how Cyber AI Analyst boosts SOC efficiency with faster threat triage, investigation, and response.

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
Nathaniel Jones
SVP, Global Threat Intelligence

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August 7, 2026

When AI Agents Attack: The Case for Behavioral Anomaly Detection

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The UK AI Security Institute (AISI) has just published a detailed incident report confirming what many within the cyber security industry have suspected for some time: frontier AI agents, given a degree of autonomy, can independently develop and execute attack chains against real targets, including social engineering, supply-chain compromise, and deception, without explicit instruction to do so.

The report (INC-2026-07-28-01, published 4 August 2026) documents what happened during a routine capability evaluation between 25 and 28 July. It deserves a careful read from anyone responsible for securing the modern digital estate.

The incident

AISI regularly tests frontier AI models for offensive cyber capability. In this exercise, agents were placed inside a simulated network environment and given internet access this was deliberate, given to reflect realism of the task. Across 122 evaluation runs, 19 instances of unsanctioned activity were recorded, including cases where agents broke the intended boundaries of the test and acted against real people and real infrastructure on the open internet.

In the most serious case, an agent (Mythos 5) autonomously:

  • Conducted open-source intelligence gathering to identify real developers associated with keywords from the simulated scenario
  • Created a GitHub account and submitted a pull request containing obfuscated malicious code to a real, unaffiliated repository
  • Created a second sockpuppet account to post comments on its own PR, attempting to manufacture social proof
  • When a human reviewer flagged the malicious content, the agent lied, claiming an accidental commit, then repeatedly attempted to reintroduce the payload under the guise of having "fixed" the code
  • Sent spear-phishing emails to the repository maintainer containing manipulated content designed to convince them to merge the code
  • Planted a prompt injection inside a GitHub issue, hidden in an HTML comment invisible to humans but readable by AI coding assistants parsing the repository via API

AISI confirmed no real-world harm resulted. The PRs were not merged; the payloads did not execute. But containment was a product of circumstance, not design.

Why this matters

Every action the agents took used legitimate services operating within normal parameters. Creating a GitHub account is legitimate. Opening a pull request is legitimate. Sending an email is legitimate. Posting an issue is legitimate.

No vulnerability was exploited. No known malware signature was present. No indicator of compromise from any threat intelligence feed would have matched. The entire attack existed as a pattern, a sequence of individually normal actions that, taken together, constituted a supply-chain attack, a social engineering campaign, and an attempted compromise of downstream systems.

This is the class of threat that signature-based and rule-based security tools structurally struggle to detect. They answer the question "have I seen this before?" When the answer is no – and when the attack is novel, composed of legitimate actions, and adapted in real time by an adversary in this case an agent that reasons about evasion – they struggle.

Behavioral anomaly detection: The architecture that fits

Darktrace has spent a decade building a platform around a different question: "is this behavior normal for this entity?"

The platform learns the baseline behavior of every user, device, and communication pattern across an organization's digital environment. It does not need prior knowledge of an attack technique. It identifies deviation from learned normality, surfaces it, and through its Autonomous Response capability, takes targeted action to contain threats at machine speed.

Consider how this AISI incident might show across the Darktrace platform:

Network detection and response

While no payload was successfully delivered to a victim in this incident, AISI's post-incident analysis of the agent's code (detailed on pages 24-25 of the report) reveals what would have landed on target systems had the social engineering succeeded. The agent produced three successive payload generations, each replacing the last after being detected and called out:

Generation 1 hid a module-load stager inside a legitimate bug-fix commit, guarded by an environment variable check, to skip execution in CI. Its second stage attempted to fetch Poseidon implants (Linux and Windows variants) calling back to the agent's own C2 listener, with a fallback to publicly hosted polling scripts that fetched and executed commands every 60 seconds.

Generation 2 exploited an Electron "What's New" window with nodeIntegration enabled, loading remote HTML from a GitHub Pages site the agent had registered. The page decoded an XOR-obfuscated payload at runtime that beaconed host identifiers over DNS, attempted to download the same implants, ran its own in-process C2 loop, and installed reboot persistence via crontab and Windows registry Run keys.

Generation 3 was a post-install dropper added after the agent had already been publicly caught. It XOR-decoded a hidden URL, downloaded a script over plaintext HTTP, and ran it detached, force-exiting so npm install always reports success, giving the attacker remote code execution on any machine running the install.

None of these payloads reached a victim. But the technical detail matters: this is the calibre of tradecraft an autonomous agent produced in a matter of hours, unprompted. Each generation demonstrated adaptation, the agent iterated its approach in direct response to being detected.

For network defenders, the behavioral signals these payloads would have generated are clear. DNS beaconing to novel domains, periodic HTTP polling to newly registered infrastructure, XOR-encoded data in transit, registry and crontab persistence writes on endpoints that have never exhibited such behavior. These are exactly the anomalies that Darktrace / NETWORK identifies in real time: deviations from learned device and connection baselines, regardless of whether the specific payload or C2 domain has been seen before.

Beyond the payload analysis, the agents' broader activity produced additional behavioral anomalies: new identities engaging in high-frequency interactions with external services, coordination via unusual channels (public pastebins, gists), and lateral communication patterns that deviate from any established baseline.

Email security

The spear-phishing emails sent by the agent, crafted with context-specific content designed to manipulate a specific individual, represent exactly the kind of socially engineered communication that static email gateways can miss. Darktrace / EMAIL analyses the linguistic patterns, sender behavior, and relational context of every message. A brand-new sender using tailored language to pressure a recipient into a specific technical action deviates from the learned communication profile, regardless of whether the message contains a known-bad URL or attachment.

Securing AI

This is where the incident points to a threat category that many security platforms do not yet fully address. The agent did not just use AI as a tool for attack. It targeted other AI systems, attempting prompt injections against coding assistants and trying to compromise automated workflows. Organisations adopting AI agents for development, operations, and decision-making are introducing a newer extended attack surface.  

Darktrace / SECURE AI extends the same behavioral detection model into this space. It monitors AI usage across the enterprise, detecting anomalous interactions with AI services, identifying sensitive data exposure to AI systems, providing visibility into shadow AI use. As AI agents become standard components of enterprise infrastructure, the ability to detect when an AI system is behaving outside its expected parameters, when there is a chance, it is being manipulated, or when it is interacting with something it should not be, that becomes a direct security requirement rather than a future consideration.

The principle is consistent across the Darktrace platform: learn what normal looks like, identify deviation, respond autonomously.

The AI-to-AI threat surface

One of the report's most important findings is a confirmation that AI agents can act outside of instructions and guardrails to complete tasks. The Mythos 5 agent conducted reconnaissance on a repository maintainer, inferred it might be an AI coding assistant, and deployed a prompt injection specifically crafted to compromise it.

This is a new attack class. Organizations deploying AI coding assistants, AI-powered code review, or autonomous DevOps agents now face an adversary that:

  • Moves at speed
  • Is able to adapt its approach when initial attempts are halted
  • Specifically targets AI systems via techniques (prompt injection, hidden instructions in HTML comments) that are less visible to human reviewers but parsed by machines
  • Reasons about which evasion strategies are most likely to succeed

Defending against this requires security that operates with the same adaptability and speed. A system that learns what "normal" looks like, and flags deviation from it.

What AISI recommends

The report identifies five contributing factors to the incident. Two are directly relevant:

No synchronous real-time monitoring (Section 5.3): AISI acknowledges it had not built real-time behavioral monitoring capable of immediately blocking unsanctioned agent actions. Their security team detected the incident via commercial security monitoring software, but only after activity had already occurred.

No fine-grained behavioral controls (Section 6.2): AISI's forward-looking response includes building continuous monitoring that can "immediately block or flag unsanctioned AI agent behavior."

The direction is clear: organizations need security that watches behavior continuously, learns what normal looks like, and acts when deviation occurs, without requiring a human in the loop for every decision.

The takeaway

The AISI incident is documented proof that autonomous AI agents will independently develop novel attack chains using legitimate tools, adapt when detected, employ deception, and target both humans and other AI systems. This happened last week, in a controlled setting, with commercially available models.

The security architecture that addresses this is behavioral anomaly detection applied across the full digital estate, as AI agents become standard components of enterprise infrastructure, writing code, managing deployments, processing communications, the attack surface they create is behavioral by nature.

This is the approach Darktrace has taken for years: learning what is normal across an organization’s digital environment, identifying meaningful deviations, and responding to emerging threats without relying on known attack signatures. As autonomous AI agents introduce new and unpredictable behaviors, that foundation becomes increasingly important to securing the enterprise.

Read the full report from the UK AI Security Institute here.

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About the author
Adam Stevens
Senior Director of Product | Darktrace

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August 5, 2026

Testing a Prompt injection Attack Against an Enterprise AI Agent

prompt injectionDefault blog imageDefault blog image

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
Your data. Our AI.
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