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August 22, 2023

Darktrace’s Detection of Unattributed Ransomware

Leveraging anomaly-based detection, we successfully identified an ongoing ransomware attack on the network of a customer and the activity that preceded it.
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
Natalia Sánchez Rocafort
Cyber Security Analyst
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22
Aug 2023

In the current threat landscape, much of the conversation around ransomware focusses on high-profile strains and notorious threat groups. While organizations and their security teams are justified in these concerns, it is important not to underestimate the danger posed by smaller scale, unattributed ransomware attacks.

Unlike attributed ransomware strains, there are often no playbooks or lists of previously observed indicators of compromise (IoCs) that security teams can consult to help them shore up their cyber defenses. As such, anomaly detection is critical to ensure that emerging threats can be detected based on their abnormality on the network, rather than relying heavily on threat intelligence.

In mid-March 2023, a Darktrace customer requested analytical support from the Darktrace Security Operations Center (SOC) after they had been hit by a ransomware attack a few hours earlier. Darktrace was able to uncover a myriad of malicious activity that preceded the eventual ransomware deployment, ultimately assisting the customer to identify compromised devices and contain the ransomware attack.

Attack Overview

While there were a small number of endpoints that had been flagged as malicious by open-source intelligence (OSINT), Darktrace DETECT™ focused on the unusualness of the activity surrounding this emerging ransomware attack. This provided unparalleled visibility over this ransomware attack at every stage of the cyber kill chain, whilst also revealing the potential origins of the compromise which came months area.

Initial Compromise

Initial investigation revealed that several devices that Darktrace were observed performing suspicious activity had previously engaged in anomalous behavior several months before the ransomware event, indicating this could be a part of a repeated compromise or the result of initial access brokers.

Most notably, in late January 2023 there was a spike in unusual activity when some of the affected devices were observed performing activity indicative of network and device scanning.

Darktrace DETECT identified some of the devices establishing unusually high volumes of internal failed connections via TCP and UDP, and the SMB protocol. Various key ports, such as 135, 139, and 445, were also scanned.

Due to the number of affected devices, the exact initial attack vector is unclear; however, one likely scenario is associated with an internet-facing DNS server. Towards the end of January 2023, the server began to receive unusual TCP DNS requests from the rare external endpoint, 103.203.59[.]3, which had been flagged as potentially malicious by OSINT [4]. Based on a portion of the hostname of the device, dc01, we can assume that this server served as a gateway to the domain controller. If a domain controller is compromised, a malicious actor would gain access to usernames and passwords within a network allowing attackers to obtain administrative-level access to an organization’s digital estate.

Around the same time as the unusual TCP DNS requests, Darktrace DETECT observed the domain controller engaging in further suspicious activity. As demonstrated in Figure 1, Darktrace recognized that this server was not responding to common requests from multiple internal devices, as it would be expected to. Following this, the device was observed carrying out new or uncommon Windows Management Instrumentation (WMI) activity. WMI is typically used by network administrators to manage remote and local Windows systems [3].

Figure 1: Device event log depicting the possible Initial attack vector.


Had Darktrace RESPOND™ been enabled in autonomous response mode, it would have to blocked connections originating from the compromised internal devices as soon as they were detected, while also limiting affected devices to their pre-established patterns of file to prevent them from carrying out any further malicious activity.

Darktrace subsequently observed multiple devices establishing various chains of connections that are indicative of lateral movement activity, such as unusual internal RDP and WMI requests. While there may be devices within an organization that do regularly partake these types of connections, Darktrace recognized that this activity was extremely unusual for these devices.

Darktrace’s Self-Learning AI allows for a deep understanding of customer networks and the devices within them. It’s anomaly-based threat detection capability enables it to recognize subtle deviations in a device’s normal patterns of behavior, without depending on known IoCs or signatures and rules to guide it.

Figure 2: Observed chain of possible lateral movement.


Persistence

Darktrace DETECT observed several affected devices communicating with rare external endpoints that had also been flagged as potentially malicious by OSINT tools. Multiple devices were observed performing activity indicative of NTLM brute-forcing activity, as seen in the Figure 3 which highlights the event log of the aforementioned domain controller. Said domain controller continuously engaged in anomalous behavior throughout the course of the attack. The same device was seen using a potentially compromise credential, ‘cvd’, which was observed via an SMB login event.

Figure 3: Continued unusual external connectivity.


Affected devices, including the domain controller, continued to engage in consistent communication with the endpoints prior to the actual ransomware attack. Darktrace identified that some of these malicious endpoints had likely been generated by Domain Generation Algorithms (DGA), a classic tactic utilized by threat actors. Subsequent OSINT investigation revealed that one such domain had been associated with malware such as TrojanDownloader:Win32/Upatre!rfn [5].

All external engagements were observed by Darktrace DETECT and would have been actioned on by Darktrace RESPOND, had it been configured in autonomous response mode. It would have blocked any suspicious outgoing connections originating from the compromised devices, thus preventing additional external engagement from taking place. Darktrace RESPOND works in tandem with DETECT to autonomously take action against suspicious activity based on its unusualness, rather than relying on static lists of ‘known-bads’ or malicious IoCs.

Reconnaissance

On March 14, 2023, a few days before the ransomware attack, Darktrace observed multiple internal devices failing to establish connections in a manner that suggests SMB, RDP and network scanning. Among these devices once more was the domain controller, which was seen performing potential SMB brute-forcing, representing yet another example of malicious activity carried out by this device.

Lateral Movement

Immediately prior to the attack, many compromised devices were observed mobilizing to conduct an array of high-severity lateral movement activity. Darktrace detected one device using two administrative credentials, namely ‘Administrator’ and ‘administrator’, while it also observed a notable spike in the volume of successful SMB connections from the device around the same time.

At this point, Darktrace DETECT was observing the progression of this attack along the cyber kill chain. What had started as internal recognisance, had escalated to exploitation and ensuing command-and-control activity. Following an SMB brute-force attempt, Darktrace DETECT identified a successful DCSync attack.

A DCSync attack occurs when a malicious actor impersonates a domain controller in an effort to gather sensitive information, such as user credentials and passwords hashes, by replicating directory services [1]. In this case, a device sent various successful DRSGetNCChanges operation requests to the DRSUAPI endpoint.

Data Exfiltration

Around the same time, Darktrace detected the compromised server transferring a high volume of data to rare external endpoints associated with Bublup, a third-party project management application used to save and share files. Although the actors attempted to avoid the detection of security tools by using a legitimate file storage service, Darktrace understood that this activity represented a deviation in this device’s expected pattern of life.

In one instance, around 8 GB of data was transferred, and in another, over 4 GB, indicating threat actors were employing a tactic known as ‘low and slow’ exfiltration whereby data is exfiltrated in small quantities via multiple connections, in an effort to mask their suspicious activity. While this tactic may have evaded the detection of traditional security measures, Darktrace’s anomaly-based detection allowed it to recognize that these two incidents represented a wider exfiltration event, rather than viewing the transfers in isolation.

Impact

Finally, Darktrace began to observe a large amount of suspicious SMB activity on the affected devices, most of which was SMB file encryption. DETECT observed the file extension ‘uw9nmvw’ being appended to many files across various internal shares and devices. In addition to this, a potential ransom note, ‘RECOVER-uw9nmvw-FILES.txt’, was detected on the network shortly after the start of the attack.

Figure 4: Depiction of the high-volume of suspicious SMB activity, including file encryption.


Conclusion

Ultimately, this incident show cases how Darktrace was able to successfully identify an emerging ransomware attack using its unrivalled anomaly-based detection capabilities, without having to rely on any previously established threat intelligence. Not only was Darktrace DETECT able to identify the ransomware at multiple stages of the kill chain, but it was also able to uncover the anomalous activity that took place in the buildup to the attack itself.

As the attack progressed along the cyber kill chain, escalating in severity at every juncture, DETECT was able to provide full visibility over the events. Through the successful identification of compromised devices, anomalous administrative credentials usage and encrypted files, Darktrace was able to greatly assist the customer, ensuring they were well-equipped to contain the incident and begin their incident management process.

Darktrace would have been able to aid the customer even further had they enabled its autonomous response technology on their network. Darktrace RESPOND would have taken targeted, mitigative action as soon as suspicious activity was detected, preventing the malicious actors from achieving their goals.

Credit to: Natalia Sánchez Rocafort, Cyber Security Analyst, Patrick Anjos, Senior Cyber Analyst.

MITRE Tactics/Techniques Mapping

RECONNAISSANCE

Scanning IP Blocks  (T1595.001)

RECONNAISSANCE

Vulnerability Scanning  (T1595.002)

IMPACT

Service Stop  (T1489)

LATERAL MOVEMENT

Taint Shared Content (T1080)

IMPACT

Data Encrypted for Impact (T1486)

INITIAL ACCESS

Replication Through Removable Media (T1200)

DEFENSE EVASION

Rogue Domain Controller (T1207)

COMMAND AND CONTROL

Domain Generation Algorithms (T1568.002)

EXECUTION

Windows Management Instrumentation (T1047)

INITIAL ACCESS

Phishing (T1190)

EXFILTRATION

Exfiltration Over C2 Channel (T1041)

IoC Table

IoC ----------- TYPE ------------- DESCRIPTION + PROBABILITY

CVD --------- credentials -------- Possible compromised credential

.UW9NMVW - File extension ----- Possible appended file extension

RECOVER-UW9NMVW-FILES.TXT - Ransom note - Possible ransom note observed

84.32.188[.]186 - IP address ------ C2 Endpoint

AS.EXECSVCT[.]COM - Hostname - C2 Endpoint

ZX.EXECSVCT[.]COM - Hostname - C2 Endpoint

QW.EXECSVCT[.]COM - Hostname - C2 Endpoint

EXECSVCT[.]COM - Hostname ------ C2 Endpoint

15.197.130[.]221 --- IP address ------ C2 Endpoint

AS59642 UAB CHERRY SERVERS - ASN - Possible ASN associated with C2 Endpoints

108.156.28[.]43

108.156.28[.]22

52.84.93[.]26

52.217.131[.]241

54.231.193[.]89 - IP addresses - Possible IP addresses associated with data exfiltration

103.203.59[.]3 -IP address ---- Possible IP address associated with initial attack vector

References:

[1] https://blog.netwrix.com/2021/11/30/what-is-dcsync-an-introduction/

[2] https://www.easeus.com/computer-instruction/delete-system32.html#:~:text=System32%20is%20a%20folder%20on,DLL%20files%2C%20and%20EXE%20files.

[3] https://www.techtarget.com/searchwindowsserver/definition/Windows-Management-Instrumentation#:~:text=WMI%20provides%20users%20with%20information,operational%20environments%2C%20including%20remote%20systems.

[4] https://www.virustotal.com/gui/ip-address/103.203.59[.]3

[5] https://otx.alienvault.com/indicator/ip/15.197.130[.]221

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
Natalia Sánchez Rocafort
Cyber Security Analyst

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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

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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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