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June 19, 2023

Darktrace Detection of 3CX Supply Chain Attack

Explore how the 3CX supply chain compromise was uncovered, revealing key insights into the detection of sophisticated cyber 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
Nahisha Nobregas
SOC Analyst
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19
Jun 2023

Ever since the discovery of the SolarWinds hack that affected tens of thousands of organizations around the world in 2020, supply chain compromises have remained at the forefront of the minds of security teams and continue to pose a significant threat to their business operations. 

Supply chain compromises can have far-reaching implications, from disrupting an organization’s daily operations, incurring huge financial and reputational damage, to affecting the critical infrastructure of entire countries. As such, it is essential for organizations to have effective security measures in place able to identify and halt these attacks at the earliest possible stage.

In March 2023 the 3CX Desktop application became the latest victim of a supply chain compromise dubbed as the “SmoothOperator” by SentinelOne. This application is used by over 600,000 companies worldwide and the customer list contains high-profile customers across a variety of industries [2]. The 3CX Desktop application is a Voice over Internet Protocol (VoIP) communication software for enterprises that allows for chats, video calls, and voice calls. [3] The 3CX installers for both Windows and macOS systems were affected by information stealing malware. Researchers were able to discern that threat actors also known as UNC 4736 related to financially motivated North Korean operators also known as AppleJeus were responsible for the supply chain compromise.  Researchers have also linked it to another supply chain compromise that occurred prior on the Trading Technologies X_TRADER platform, making this the first known cascading software supply chain compromise used to distribute malware on a wide scale and still be able to align operator interests. [3] Customer reports following the compromise began to surface about the 3CX software being picked up as malicious by several cybersecurity vendors such as CrowdStrike, SentinelOne, and Palo Alto Networks. [6] 

By leveraging integrations with other security vendors like CrowdStrike and SentinelOne, Darktrace was able to identify activity from the “SmoothOperator” across the customer base at multiple stages of the kill chain in March 2023. Darktrace RESPOND™ was then able to autonomously intervene against these emerging threats, preventing significant disruption to customer networks. 

Background on the first known cascading supply chain attack 

Initial Access

In April 2023, security researchers identified the initial target in this story was not the 3CX desktop application, rather, it was another software application called X_TRADER by Trading Technologies. [3] Trading Technologies is a provider that offers high-performance financial trading packages, allowing financial professionals to analyze and trade assets within the stock market more efficiently. Unfortunately, a compromise already existed in the supply chain for this organization. The X_TRADER installer, which had been retired in 2020, still had its code signing certificate set to expire in October 2022. This code signing certificate was exploited by attackers to digitally sign the malicious software. [3] It also inopportunely led to 3CX when an employee unknowingly downloaded a trojanized installer for the X_TRADER software from Trading Technologies prior to the certificate’s expiration. [4]. This compromise of 3CX via X_TRADER was the first case of a cascading supply chain attack reported on within the wider threat landscape. 

Persistence and Privilege Escalation 

Following these findings, researchers were able to identify the likely kill chain that occurred on Windows systems, beginning with the download of the 3CX DesktopApp installer that executed an executable (.exe) file before dropping two trojanized Data Link Libraries (DLLs) alongside a benign executable that was used to sideload malicious DLLs. These DLLs contained and used SIGFLIP and DAVESHELL; both publicly available projects. [3] In this case, the DLLs were used to decrypt using an RC4 key and load a payload into the memory of a compromised system. [3] SIGFLIP and DAVESHELL also extract and decrypt the modular backdoor named VEILEDSIGNAL, which also contains a command and control (C2) configuration. This malware allowed the North Korean threat operators to gain administrative control to the 3CX employee’s device. [3] This was followed by access to the employee’s corporate credentials, ultimately leading to access to 3CX systems. [4] 

Lateral Movement and C2 activity

Security researchers were also able to identify other malware families that were mainly utilized in the supply chain attack to move laterally within the 3CX environment, and allow for C2 communication [3], these malware families are detailed below:

  • TaxHaul: when executed it decrypts shellcode payload, observed by Mandiant to persist via DLL search-order hijacking.
  • Coldcat: complex downloader, which also beacons to a C2 infrastructure.
  • PoolRat: collects system information and executes commands. This is the malware that was found to affect macOS systems.
  • IconicStealer: served as a third stage payload on 3CX systems to steal data or information.

Furthermore, it was also reported early on by Kaspersky that a backdoor named Gopuram, routinely used by the North Korean threat actors Lazarus and typically used against cryptocurrency companies, was also used as a second stage payload on a limited number of 3CX’s customers compromised systems. [5]

3CX detections observed by Darktrace

CrowdStrike and SentinelOne, two of the major detection platforms with which Darktrace partners through security integrations, initially revealed that their platforms had identified the campaign appeared to be targeting 3CXDesktopApp customers in March 2023. 

At this time, Darktrace was also observing this activity and alerting customers to unusual behavior on their networks. [1][7] Darktrace DETECT identified activity related to the supply chain compromise primarily through host-level alerts associated with CrowdStrike and SentinelOne integrations, as well as model breaches related to lateral movement and C2 activity. 

Some of the activity related to the 3CX supply chain compromise that Darktrace detected was observed solely via integration models picking up executable and Microsoft Software Installer (msi) file downloads for the 3CXDesktopApp, suggesting the compromise likely was stopped at the endpoint device. 

CrowdStrike integration model breach identifying 3CXDesktopApp[.]exe as possible malware
Figure 1: CrowdStrike integration model breach identifying 3CXDesktopApp[.]exe as possible malware on March 30, 2023.
showcases the Model Breach Event Log for the CrowdStrike integration model breach
Figure 2: The above figure, showcases the Model Breach Event Log for the CrowdStrike integration model breach shown in Figure 1.

In another case highlighted in Figure 3 and 4, security platforms were associating 3CX as malicious. The device in these figures was observed downloading a 3CXDesktopApp executable followed by an msi file about an hour later. This pattern of activity correlates with the compromise process that had been on reported, where the “SmoothOperator” malware that affected 3CX systems was able to persist through DLL side-loading of malicious DLL files delivered with benign executable files, making it difficult for traditional security tools to detect. [2][3][7]

The activity in this case was detected by the DETECT integration model, ‘High Severity Integration Malware Detection’ and was later blocked by the Darktrace RESPOND/Network model, ‘Antigena Significant Anomaly from Client Block’ which applied the “Enforce Pattern of Life” action to intercept the malicious download that was taking place. Darktrace RESPOND uses AI to learn every devices normal pattern of life and act autonomously to enforce its normal activity. In this event, RESPOND would not only intercept the malicious download that was taking place on the device, but also not allow the device to significantly deviate from its normal pattern of activity.

The Model Breach Event log for the device displays the moment in which the SentinelOne integration model breached for the 3CXDesktopApp.exe file
Figure 3: The Model Breach Event log for the device displays the moment in which the SentinelOne integration model breached for the 3CXDesktopApp.exe file followed subsequently by the RESPOND model, ‘Antigena Significant Anomaly from Client Block’, on March 29, 2023.
Another ‘High Severity Integration Malware Detection’ breached
Figure 4: Another ‘High Severity Integration Malware Detection’ breached for the same device in Figure 3 approximately one hour later because of the msi file, 3CXDesktopApp-18.12.416.msi, which also led to the Darktrace RESPOND model, ‘Antigena Significant Anomaly from Client Block’, on March 29, 2023.

In a separate case, Darktrace also detected a device performing unusual SMB drive writes for the file ‘3CXDesktopApp-18.10.461.msi’. This breached the DETECT model ‘SMB Drive Write’. This model detects when a device starts writing files to another internal device it does not usually communicate with via the SMB protocol using the admin$ or drive shares.

This Model Breach Event log highlights the moment Darktrace captured the msi application file for the 3CXDesktopApp being transferred internally on this customer’s network
Figure 5: This Model Breach Event log highlights the moment Darktrace captured the msi application file for the 3CXDesktopApp being transferred internally on this customer’s network, this was picked up as new activity for the device on March 28, 2023. 

In a couple of other cases observed by Darktrace, connections detected were made from affected devices to 3CX compromise related endpoints. In Figure 6, the device in question was detected connecting to the endpoint, journalide[.]org. This breached the model, ‘Suspicious Self-Signed SSL’, which looks for connections being made to an endpoint with a self-signed SSL certificate which is designed to look legitimate, as self-signed certificates are often used in malware communication.

Model Breach Event log for connections to the 3CX C2 related endpoint
Figure 6: Model Breach Event log for connections to the 3CX C2 related endpoint, journalide[.]org, these connections breached the model Suspicious Self-Signed SSL on April 24, 2023.

On another Darktrace customer environment, a 3CX C2 endpoint, pbxphonenetwork[.]com, had already been added to the Watched Domains list around the time reports of the 3CX application software being malicious had been reported. The Watched Domains list allows Darktrace to detect if any device on the network makes connections to these domains with more scrutiny and breach a model for further visibility of threats on the network. Activity in this case was detected and subsequently blocked by a Darktrace RESPOND action, “Block connections to 89.45.67[.]160 port 443 and pbxphonenetwork[.]com on port 443”, blocking the device from connecting to this 3CX C2 endpoints on the spot (see Figure 7). This activity subsequently breached the RESPOND model, ‘Antigena Watched Domain Block’. 

Figure 7: History log of the Darktrace RESPOND action applied to the device breaching the Darktrace RESPOND model, Antigena Watched Domain Block and applying the action, “Block connections to 89.45.67[.]160 port 443 and pbxphonenetwork[.]com on port 443” on March 31, 2023.

Darktrace Coverage 

Utilizing integrations with Darktrace such as those with CrowdStrike and SentinelOne, Darktrace was able to detect and respond to activity identified as malicious 3CX activity by CrowdStrike and SentinelOne as seen in Figures 1, 2, 3, and 4. This activity breached the following Darktrace DETECT models: 

  • Integration / CrowdStrike Alert
  • Security Integration / High Severity Integration Malware Detection

Darktrace was also able to identify lateral movement activity such as in the case illustrated in Figure 5.

  • Compliance / SMB Drive Write

Lastly, C2 beaconing activity from malicious endpoints associated with the 3CX compromise was also detected as seen in Figure 6, this activity breached the following Darktrace DETECT model:

  • Anomalous Connection / Suspicious Self-Signed SSL

For customers with Darktrace RESPOND configured in autonomous response mode, Darktrace RESPOND models also breached to activity related to the 3CX supply chain compromise as seen in Figures 3, 4, and 7. Below are the models that breached and the following autonomous actions that were applied:

  • Antigena / Network / Significant Anomaly / Antigena Significant Anomaly from Client Block, “Enforce pattern of life”
  • Antigena / Network / External Threat / Antigena Watched Domain Block, “Block connections to 89.45.67[.]160 port 443 and pbxphonenetwork[.]com on port 443”

Conclusion 

The first known cascading supply chain compromise occurred inopportunely for 3CX but conveniently for UNC 4736 North Korean threat actors. This “SmoothOperator” compromise was detected by endpoint security platforms such as CrowdStrike who was at the cusp of this discovery when it became one of the first platforms to report on malicious activity related to the 3CX DesktopApp supply chain compromise.  

Although still novel at the time and largely without reported indicators of compromise, Darktrace was able to capture and identify activity related to the 3CX compromise across its customer base, as well as respond autonomously to contain it. Darktrace was able to amplify security integrations with CrowdStrike and SentinelOne, and via anomaly-based model breaches, contribute unique insights by highlighting activity in varied parts of the 3CX supply chain compromise kill chain. The “SmoothOperator” supply chain attack proves that the Darktrace suite of products, including DETECT and RESPOND, can not only act autonomously to identify and respond to novel threats, but also work with security integrations to further amplify intervention and prevent cyber disruption on customer networks. 

Credit to Nahisha Nobregas, SOC Analyst and Trent Kessler, SOC Analyst.

Appendices

MITRE ATT&CK Framework

Resource Development

  • T1588 Obtain Capabilities  
  • T1588.004 Digital Certificates
  • T1608 Stage Capabilities  
  • T1608.003 Install Digital Certificate

Initial Access

  • T1190 Exploit Public-Facing Application
  • T1195 Supply Chain Compromise  
  • T1195.002 Compromise Software Supply Chain

Persistence

  • T1574 Hijack Execution Flow
  • T1574.002 DLL Side-Loading

Privilege Escalation

  • T1055 Process Injection
  • T1574 Hijack Execution Flow  
  • T1574.002 DLL Side-Loading

Command and Control

  • T1071 Application Layer Protocol
  • T1071.001 Web Protocols
  • T1071.004 DNS  
  • T1105 Ingress Tool Transfer
  • T1573 Encrypted Channel

List of IOCs

C2 Hostnames

  • journalide[.]org
  • pbxphonenetwork[.]com

Likely C2 IP address

  • 89.45.67[.]160

References

  1. https://www.crowdstrike.com/blog/crowdstrike-detects-and-prevents-active-intrusion-campaign-targeting-3cxdesktopapp-customers/
  2. https://www.bleepingcomputer.com/news/security/3cx-confirms-north-korean-hackers-behind-supply-chain-attack/
  3. https://www.mandiant.com/resources/blog/3cx-software-supply-chain-compromise
  4. https://www.securityweek.com/cascading-supply-chain-attack-3cx-hacked-after-employee-downloaded-trojanized-app/
  5. https://securelist.com/gopuram-backdoor-deployed-through-3cx-supply-chain-attack/109344/
  6. https://www.bleepingcomputer.com/news/security/3cx-hack-caused-by-trading-software-supply-chain-attack/
  7. https://www.sentinelone.com/blog/smoothoperator-ongoing-campaign-trojanizes-3cx-software-in-software-supply-chain-attack/
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
Nahisha Nobregas
SOC Analyst

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August 6, 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. The defense must be too.

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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