Blog
/
Network
/
August 27, 2024

Decrypting the Matrix: How Darktrace Uncovered a KOK08 Ransomware Attack

In May 2024, a Darktrace customer was affected by KOK08, a ransomware strain commonly used by the Matrix ransomware family. Learn more about the tactics used by this ransomware case, including double extortion, and how Darktrace is able to detect and respond to such threats.
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
Christina Kreza
Cyber Analyst
Decrypting the Matrix: How Darktrace Uncovered a KOK08 Ransomware AttackDefault blog image
27
Aug 2024

What is Matrix Ransomware?

Matrix is a ransomware family that first emerged in December 2016, mainly targeting small to medium-sized organizations across the globe in countries including the US, Belgium, Germany, Canada and the UK [1]. Although the reported number of Matrix ransomware attacks has remained relatively low in recent years, it has demonstrated ongoing development and gradual improvements to its tactics, techniques, and procedures (TTPs).

How does Matrix Ransomware work?

In earlier versions, Matrix utilized spam email campaigns, exploited Windows shortcuts, and deployed RIG exploit kits to gain initial access to target networks. However, as the threat landscape changed so did Matrix’s approach. Since 2018, Matrix has primarily shifted to brute-force attacks, targeting weak credentials on Windows machines accessible through firewalls. Attackers often exploit common and default credentials, such as “admin”, “password123”, or other unchanged default settings, particularly on systems with Remote Desktop Protocol (RDP) enabled [2] [3].

Darktrace observation of Matrix Ransomware tactics

In May 2024, Darktrace observed an instance of KOK08 ransomware, a specific strain of the Matrix ransomware family, in which some of these ongoing developments and evolutions were observed. Darktrace detected activity indicative of internal reconnaissance, lateral movement, data encryption and exfiltration, with the affected customer later confirming that credentials used for Virtual Private Network (VPN) access had been compromised and used as the initial attack vector.

Another significant tactic observed by Darktrace in this case was the exfiltration of data following encryption, a hallmark of double extortion. This method is employed by attacks to increase pressure on the targeted organization, demanding ransom not only for the decryption of files but also threatening to release the stolen data if their demands are not met. These stakes are particularly high for public sector entities, like the customer in question, as the exposure of sensitive information could result in severe reputational damage and legal consequences, making the pressure to comply even more intense.

Darktrace’s Coverage of Matrix Ransomware

Internal Reconnaissance and Lateral Movement

On May 23, 2024, Darktrace / NETWORK identified a device on the customer’s network making an unusually large number of internal connections to multiple internal devices. Darktrace recognized that this unusual behavior was indicative of internal scanning activity. The connectivity observed around the time of the incident indicated that the Nmap attack and reconnaissance tool was used, as evidenced by the presence of the URI “/nice ports, /Trinity.txt.bak”.

Although Nmap is a crucial tool for legitimate network administration and troubleshooting, it can also be exploited by malicious actors during the reconnaissance phase of the attack. This is a prime example of a ‘living off the land’ (LOTL) technique, where attackers use legitimate, pre-installed tools to carry out their objectives covertly. Despite this, Darktrace’s Self-Learning AI had been continually monitoring devices across the customers network and was able to identify this activity as a deviation from the device’s typical behavior patterns.

The ‘Device / Attack and Recon Tools’ model alert identifying the active usage of the attack and recon tool, Nmap.
Figure 1: The ‘Device / Attack and Recon Tools’ model alert identifying the active usage of the attack and recon tool, Nmap.
Figure 2: Cyber AI Analyst Investigation into the ‘Scanning of Multiple Devices' incident.

Darktrace subsequently observed a significant number of connection attempts using the RDP protocol on port 3389. As RDP typically requires authentication, multiple connection attempts like this often suggest the use of incorrect username and password combinations.

Given the unusual nature of the observed activity, Darktrace’s Autonomous Response capability would typically have intervened, taking actions such as blocking affected devices from making internal connections on a specific port or restricting connections to a particular device. However, Darktrace was not configured to take autonomous action on the customer’s network, and thus their security team would have had to manually apply any mitigative measures.

Later that day, the same device was observed attempting to connect to another internal location via port 445. This included binding to the server service (srvsvc) endpoint via DCE/RPC with the “NetrShareEnum” operation, which was likely being used to list available SMB shares on a device.

Over the following two days, it became clear that the attackers had compromised additional devices and were actively engaging in lateral movement. Darktrace detected two more devices conducting network scans using Nmap, while other devices were observed making extensive WMI requests to internal systems over DCE/RPC. Darktrace recognized that this activity likely represented a coordinated effort to map the customer’s network and identity further internal devices for exploitation.

Beyond identifying the individual events of the reconnaissance and lateral movement phases of this attack’s kill chain, Darktrace’s Cyber AI Analyst was able to connect and consolidate these activities into one comprehensive incident. This not only provided the customer with an overview of the attack, but also enabled them to track the attack’s progression with clarity.

Furthermore, Cyber AI Analyst added additional incidents and affected devices to the investigation in real-time as the attack unfolded. This dynamic capability ensured that the customer was always informed of the full scope of the attack. The streamlined incident consolidation and real-time updates saved valuable time and resources, enabling quicker, more informed decision-making during a critical response window.

Cyber AI Analyst timeline showing an overview of the scanning related activity, while also connecting the suspicious lateral movement activity.
Figure 3: Cyber AI Analyst timeline showing an overview of the scanning related activity, while also connecting the suspicious lateral movement activity.

File Encryption

On May 28, 2024, another device was observed connecting to another internal location over the SMB filesharing protocol and accessing multiple files with a suspicious extension that had never previously been observed on the network. This activity was a clear sign of ransomware infection, with the ransomware altering the files by adding the “KOK08@QQ[.]COM” email address at the beginning of the filename, followed by a specific pattern of characters. The string consistently followed a pattern of 8 characters (a mix of uppercase and lowercase letters and numbers), followed by a dash, and then another 8 characters. After this, the “.KOK08” extension was appended to each file [1][4].

Cyber AI Analyst Investigation Process for the 'Possible Encryption of Files over SMB' incident.
Figure 4: Cyber AI Analyst Investigation Process for the 'Possible Encryption of Files over SMB' incident.
Cyber AI Analyst Encryption Information identifying the ransomware encryption activity,
Figure 5: Cyber AI Analyst Encryption Information identifying the ransomware encryption activity.

Data Exfiltration

Shortly after the encryption event, another internal device on the network was observed uploading an unusually large amount of data to the rare external endpoint 38.91.107[.]81 via SSH. The timing of this activity strongly suggests that this exfiltration was part of a double extortion strategy. In this scenario, the attacker not only encrypts the target’s files but also threatens to leak the stolen data unless a ransom is paid, leveraging both the need for decryption and the fear of data exposure to maximize pressure on the victim.

The full impact of this double extortion tactic became evident around two months later when a ransomware group claimed possession of the stolen data and threatened to release it publicly. This development suggested that the initial Matrix ransomware attackers may have sold the exfiltrated data to a different group, which was now attempting to monetize it further, highlighting the ongoing risk and potential for exploitation long after the initial attack.

External data being transferred from one of the involved internal devices during and after the encryption took place.
Figure 6: External data being transferred from one of the involved internal devices during and after the encryption took place.

Unfortunately, because Darktrace’s Autonomous Response capability was not enabled at the time, the ransomware attack was able to escalate to the point of data encryption and exfiltration. However, Darktrace’s Security Operations Center (SOC) was still able to support the customer through the Security Operations Support service. This allowed the customer to engage directly with Darktrace’s expert analysts, who provided essential guidance for triaging and investigating the incident. The support from Darktrace’s SOC team not only ensured the customer had the necessary information to remediate the attack but also expedited the entire process, allowing their security team to quickly address the issue without diverting significant resources to the investigation.

Conclusion

In this Matrix ransomware attack on a Darktrace customer in the public sector, malicious actors demonstrated an elevated level of sophistication by leveraging compromised VPN credentials to gain initial access to the target network. Once inside, they exploited trusted tools like Nmap for network scanning and lateral movement to infiltrate deeper into the customer’s environment. The culmination of their efforts was the encryption of files, followed by data exfiltration via SSH, suggesting that Matrix actors were employing double extortion tactics where the attackers not only demanded a ransom for decryption but also threatened to leak sensitive information.

Despite the absence of Darktrace’s Autonomous Response at the time, its anomaly-based approach played a crucial role in detecting the subtle anomalies in device behavior across the network that signalled the compromise, even when malicious activity was disguised as legitimate.  By analyzing these deviations, Darktrace’s Cyber AI Analyst was able to identify and correlate the various stages of the Matrix ransomware attack, constructing a detailed timeline. This enabled the customer to fully understand the extent of the compromise and equipped them with the insights needed to effectively remediate the attack.

Credit to Christina Kreza (Cyber Analyst) and Ryan Traill (Threat Content Lead)

Appendices

Darktrace Model Detections

·       Device / Network Scan

·       Device / Attack and Recon Tools

·       Device / Possible SMB/NTLM Brute Force

·       Device / Suspicious SMB Scanning Activity

·       Device / New or Uncommon SMB Named Pipe

·       Device / Initial Breach Chain Compromise

·       Device / Multiple Lateral Movement Model Breaches

·       Device / Large Number of Model Breaches from Critical Network Device

·       Device / Multiple C2 Model Breaches

·       Device / Lateral Movement and C2 Activity

·       Anomalous Connection / SMB Enumeration

·       Anomalous Connection / New or Uncommon Service Control

·       Anomalous Connection / Multiple Connections to New External TCP Port

·       Anomalous Connection / Data Sent to Rare Domain

·       Anomalous Connection / Uncommon 1 GiB Outbound

·       Unusual Activity / Enhanced Unusual External Data Transfer

·       Unusual Activity / SMB Access Failures

·       Compromise / Ransomware / Suspicious SMB Activity

·       Compromise / Suspicious SSL Activity

List of Indicators of Compromise (IoCs)

·       .KOK08 -  File extension - Extension to encrypted files

·       [KOK08@QQ[.]COM] – Filename pattern – Prefix of the encrypted files

·       38.91.107[.]81 – IP address – Possible exfiltration endpoint

MITRE ATT&CK Mapping

·       Command and control – Application Layer Protocol – T1071

·       Command and control – Web Protocols – T1071.001

·       Credential Access – Password Guessing – T1110.001

·       Discovery – Network Service Scanning – T1046

·       Discovery – File and Directory Discovery – T1083

·       Discovery – Network Share Discovery – T1135

·       Discovery – Remote System Discovery – T1018

·       Exfiltration – Exfiltration Over C2 Channer – T1041

·       Initial Access – Drive-by Compromise – T1189

·       Initial Access – Hardware Additions – T1200

·       Lateral Movement – SMB/Windows Admin Shares – T1021.002

·       Reconnaissance – Scanning IP Blocks – T1595.001

References

[1] https://unit42.paloaltonetworks.com/matrix-ransomware/

[2] https://www.sophos.com/en-us/medialibrary/PDFs/technical-papers/sophoslabs-matrix-report.pdf

[3] https://cyberenso.jp/en/types-of-ransomware/matrix-ransomware/

[4] https://www.pcrisk.com/removal-guides/10728-matrix-ransomware

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
Christina Kreza
Cyber Analyst

More in this series

No items found.

Blog

/

Network

/

August 6, 2026

When AI Agents Attack: The Case for Behavioral Anomaly Detection

Default blog imageDefault blog image

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. The defense must be too.

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

Continue reading
About the author
Adam Stevens
Senior Director of Product | Darktrace

Blog

/

/

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.

Continue reading
About the author
Carlo Loregian
Solutions Engineer
Your data. Our AI.
Elevate your network security with Darktrace AI