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January 17, 2024

Detecting Trusted Network Relationship Abuse

Discover how Darktrace DETECT and the SOC team responded to a network compromise via a trusted partner relationship with this case study.
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
Adam Potter
Senior Cyber Analyst
Written by
Taylor Breland
Analyst Team Lead, San Francisco
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17
Jan 2024

Trusted relationships between organizations and third parties have become an increasingly popular target for cyber threat actors to gain access to sensitive networks. These relationships are typically granted by organizations to external or adjacent entities and allow for the access of internal resources for business purposes.1 Trusted network relations can exist between constituent elements of an overarching corporation, IT-service providers and their customers, and even implicitly between IT product vendors and their customers.

Several high-profile compromises have occurred due to the leveraging of privileged network access by such third parties. One prominent example is the 2016 DNC network attack, in which the trust between the Democratic Congressional Campaign Committee (DCCC) and the Democratic National Committee (DNC) was exploited. Supply chain attacks, which also leverage the implicit trust between IT vendors and customers, are also on the rise with some estimates projecting that by 2025, almost half of all organizations will be impact by supply chain compromises.2 These trends may also be attributed to the prevalence of remote work as well as the growth in IT-managed service providers.3

Given the nature of such network relationships and threat techniques, signatures-based detection is heavily disadvantaged in the identification and mitigation of such trust abuses; network administrators cannot as easily use firewalls to block IPs that need access to networks. However, Darktrace DETECT™, and its Self-Learning AI, has proven successful in the identification and mitigation of these compromises. In September 2023, Darktrace observed an incident involving the abuse of such a trusted relationship on the network of a healthcare provider.

Attack Overview

In early September 2023, a Darktrace customer contacted the Darktrace Security Operations Center (SOC) through the Ask the Expert™ (ATE) service requesting assistance with suspicious activity detected on their network. Darktrace had alerted the customer’s security team to an unknown device that had appeared on their network and proceeded to perform a series of unexpected activities, including reconnaissance, lateral movement, and attempted data exfiltration.

Unfortunately for this customer, Darktrace RESPOND™ was not enabled in autonomous response mode at the time of this compromise, meaning any preventative actions suggested by RESPOND had to be applied manually by the customer’s security team after the fact.  Nevertheless, Darktrace’s prompt identification of the suspicious activity and the SOC’s investigation helped to disrupt the intrusion in its early stages, preventing it from developing into a more disruptive compromise.

Initial Access

Darktrace initially observed a new device that appeared within the customers internal network with a Network Address Translated (NAT) IP address that suggested remote access from a former partner organization’s network. Further investigation carried out by the customer revealed that poor credential policies within the partner’s organization had likely been exploited by attackers to gain access to a virtual desktop interface (VDI) machine.

Using the VDI appliance of a trusted associate, the threat actor was then able to gain access to the customer’s environment by utilizing NAT remote access infrastructure. Devices within the customer’s network had previously been utilized for remote access from the partner network when such activity was permitted and expected. Since then, access to this network was thought to have been removed for all parties. However, it became apparent that the remote access functionality remained operational. While the customer also had firewalls within the environment, a misconfiguration at the time of the attack allowed inbound port access to the remote environment resulting in the suspicious device joining the network on August 29, 2023.

Internal Reconnaissance

Shortly after the device joined the network, Darktrace observed it carrying out a string of internal reconnaissance activity. This activity was initiated with internal ICMP address connectivity, followed by internal TCP connection attempts to a range of ports associated with critical services like SMB, RDP, HTTP, RPC, and SSL. The device was also detected attempting to utilize privileged credentials, which were later identified as relating to a generic multi-purpose administrative account. The threat actor proceeded to conduct further internal reconnaissance, including reverse DNS sweeps, while also attempting to use six additional user credentials.

In addition to the widespread internal connectivity, Darktrace observed persistent connection attempts focused on the RDP and SMB protocols. Darktrace also detected additional SMB enumeration during this phase of the attacker’s reconnaissance. This reconnaissance activity largely attempted to access a wide variety of SMB shares, previously unseen by the host to identify available share types and information available for aggregation. As such, the breach host conducted a large spike in SMB writes to the server service (srvsvc) endpoint on a range of internal hosts using the credential: extramedwb. SMB writes to this endpoint traditionally indicate binding attempts.

Beginning on August 31, Darktrace identified a new host associated with the aforementioned NAT IP address. This new host appeared to have taken over as the primary host conducting the reconnaissance and lateral movement on the network taking advantage of the VDI infrastructure. Like the previous host, this one was observed sustaining reconnaissance activity on August 31, featuring elevated SMB enumeration, SMB access failures, RDP connection attempts, and reverse DNS sweeps.  The attackers utilized several credentials to execute their reconnaissance, including generic and possibly default administrative credentials, including “auditor” and “administrator”.

Figure 1: Advanced Search query highlighting anomalous activity from the second observed remote access host over the course of one week surrounding the time of the breach.

Following these initial detections by Darktrace DETECT, Darktrace’s Cyber AI Analyst™ launched an autonomous investigation into the scanning and privileged internal connectivity and linked these seemingly separate events together into one wider internal reconnaissance incident.

Figure 2: Timeline of an AI Analyst investigation carried out between August 29 and August 31, 2023, during which it detected an increased volume of scanning and unusual privileged internal connectivity.

Lateral Movement

Following the reconnaissance activity performed by the new host observed exploiting the remote access infrastructure, Darktrace detected an increase in attempts to move laterally within the customer’s network, particularly via RPC commands and SMB file writes.

Specifically, the threat actor was observed attempting RPC binds to several destination devices, which can be used in the calling of commands and/or the creation of services on destination devices. This activity was highlighted in repeated failed attempts to bind to the ntsvcs named pipe on several destination devices within the network. However, given the large number of connection attempts, Darktrace did also detect a number of successful RPC connections.

Darktrace also detected a spike in uncommon service control (SVCCTL) ExecMethod, Create, and Start service operations from the breach device.

Figure 3: Model breach details noting the affected device performing unsuccessful RPC binds to endpoints not supported on the destination device.

Additional lateral movement activity was performed using the SMB/NTLM protocols. The affected device also conducted a series of anonymous NTLM logins, whereby NTLM authentication attempts occurred without a named client principal, to a range of internal hosts. Such activity is highly indicative of malicious or unauthorized activity on the network. The host also employed the outdated SMB version 1 (SMBv1) protocol during this phase of the kill chain. The use of SMBv1 often represents a compliance issue for most networks due to the high number of exploitable vulnerabilities associated with this version of the protocol.

Lastly, Darktrace identified the internal transfer of uncommon executables, such as ‘TRMtZSqo.exe’, via SMB write. The breach device was observed writing this file to the hidden administrative share (ADMIN$) on a destination server. Darktrace recognized that this activity was highly unusual for the device and may have represented the threat actor transferring a malicious payload to the destination server for further persistence, data aggregation, and/or command and control (C2) operations. Further SMB writes of executable files, and the subsequent delete of these binaries, were observed from the device at this time. For example, the additional executable ‘JAqfhBEB.exe’ was seen being deleted by the breach device. This deletion, paired with the spike in SVCCTL Create and Start operations occurring, suggests the transfer, execution, and removal of persistence and data harvesting binaries within the network.

Figure 4: AI Analyst details highlighting the SMB file writes of the unusual executable from the remote access device during the compromise.

Conclusion

Ultimately, Darktrace was able to successfully identify and alert for suspicious activity being performed by a threat actor who had gained unauthorized access to the customer’s network by abusing one of their trusted relationships.

The identification of scanning, RPC commands and SMB sessions directly assisted the customer in their response to contain and mitigate this intrusion. The investigation carried out by the Darktrace SOC enabled the customer to promptly triage and remediate the attack, mitigating the potential damage and preventing the compromise from escalating further. Had Darktrace RESPOND been enabled in autonomous response mode at the time of the attack, it would have been able to take swift action to inhibit the scanning, share enumerations and file write activity, thereby thwarting the attacker’s network reconnaissance and lateral movement attempts.

By exploiting trusted relationships between organizations, threat actors are often able to bypass traditional signatured-based security methods that have previously been reconfigured to allow and trust connections from and to specific endpoints. Rather than relying on the configurations of specific rules and permitted IP addresses, ports, and devices, Darktrace DETECT’s anomaly-based approach to threat detection meant it was able to identify suspicious network activity at the earliest stage, irrespective of the offending device and whether the domain or relationship was trusted.

Credit to Adam Potter, Cyber Security Analyst, Taylor Breland, Analyst Team Lead, San Francisco.

Darktrace DETECT Model Breach Coverage:

  • Device / ICMP Address Scan
  • Device / Network Scan
  • Device / Suspicious SMB Scanning Activity
  • Device / RDP Scan
  • Device / Possible SMB/NTLM Reconnaissance
  • Device / Reverse DNS Sweep
  • Anomalous Connection / SMB Enumeration
  • Device / Large Number of Model Breaches
  • Anomalous Connection / Suspicious Activity On High Risk Device
  • Unusual Activity / Possible RPC Recon Activity
  • Device / Anonymous NTLM Logins
  • Anomalous Connection / Unusual SMB Version 1 Connectivity
  • Device / Repeated Unknown RPC Service Bind Errors
  • Anomalous Connection / New or Uncommon Service Control
  • Compliance / SMB Drive Write
  • Anomalous File / Internal / Unusual Internal EXE File Transfer
  • Device / Multiple Lateral Movement Model Breaches

AI Analyst Incidents:

  • Scanning of Multiple Devices
  • Extensive Unusual RDPConnections
  • SMB Write of Suspicious File
  • Suspicious DCE-RPC Activity

MITRE ATT&CK Mapping

  • Tactic: Initial Access
  • Technique: T1199 - Trusted Relationship
  • Tactic: Discovery
  • Technique:
  • T1018 - Remote System Discovery
  • T1046 - Network Service Discovery
  • T1135 - Network Share Discovery
  • T1083 - File and Directory Discovery
  • Tactic: Lateral Movement
  • Technique:
  • T1570 - Lateral Tool Transfer
  • T1021 - Remote Services
  • T1021.002 - SMB/Windows Admin Shares
  • T1021.003 - Distributed Component Object Model
  • T1550 - Use Alternate Authentication Material

References

1https://attack.mitre.org/techniques/T1199/

2https://www.cloudflare.com/learning/insights-supply-chain-attacks/

3https://newsroom.cisco.com/c/r/newsroom/en/us/a/y2023/m09/companies-reliance-on-it-managed-services-increases-in-2023-sector-valued-at-us-472-billion-globally.html#:~:text=IT%20channel%20partners%20selling%20managed,US%24419%20billion%20in%202022.

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
Adam Potter
Senior Cyber Analyst
Written by
Taylor Breland
Analyst Team Lead, San Francisco

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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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