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February 24, 2024

Quasar Remote Access Tool and Its Security Risks

Discover how the Quasar remote access tool can become a vulnerability in the wrong hands and strategies to mitigate these risks.
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
Nicole Wong
Cyber Security Analyst
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24
Feb 2024

The threat of interoperability

As the “as-a-Service” market continues to grow, indicators of compromise (IoCs) and malicious infrastructure are often interchanged and shared between multiple malware strains and attackers. This presents organizations and their security teams with a new threat: interoperability.

Interoperable threats not only enable malicious actors to achieve their objectives more easily by leveraging existing infrastructure and tools to launch new attacks, but the lack of clear attribution often complicates identification for security teams and incident responders, making it challenging to mitigate and contain the threat.

One such threat observed across the Darktrace customer base in late 2023 was Quasar, a legitimate remote administration tool that has becoming increasingly popular for opportunistic attackers in recent years. Working in tandem, the anomaly-based detection of Darktrace DETECT™ and the autonomous response capabilities of Darktrace RESPOND™ ensured that affected customers were promptly made aware of any suspicious activity on the attacks were contained at the earliest possible stage.

What is Quasar?

Quasar is an open-source remote administration tool designed for legitimate use; however, it has evolved to become a popular tool used by threat actors due to its wide array of capabilities.  

How does Quasar work?

For instance, Quasar can perform keylogging, take screenshots, establish a reverse proxy, and download and upload files on a target device [1].  A report released towards the end of 2023 put Quasar back on threat researchers’ radars as it disclosed the new observation of dynamic-link library (DLL) sideloading being used by malicious versions of this tool to evade detection [1].  DLL sideloading involves configuring legitimate Windows software to run a malicious file rather than the legitimate file it usually calls on as the software loads.  The evolving techniques employed by threat actors using Quasar highlights defenders’ need for anomaly-based detections that do not rely on pre-existing knowledge of attacker techniques, and can identify and alert for unusual behavior, even if it is performed by a legitimate application.

Although Quasar has been used by advanced persistent threat (APT) groups for global espionage operations [2], Darktrace observed the common usage of default configurations for Quasar, which appeared to use shared malicious infrastructure, and occurred alongside other non-compliant activity such as BitTorrent use and cryptocurrency mining.  

Quasar Attack Overview and Darktrace Coverage

Between September and October 2023, Darktrace detected multiple cases of malicious Quasar activity across several customers, suggesting probable campaign activity.  

Quasar infections can be difficult to detect using traditional network or host-based tools due to the use of stealthy techniques such as DLL side-loading and encrypted SSL connections for command-and control (C2) communication, that traditional security tools may not be able to identify.  The wide array of capabilities Quasar possesses also suggests that attacks using this tool may not necessarily be modelled against a linear kill chain. Despite this, the anomaly-based detection of Darktrace DETECT allowed it to identify IoCs related to Quasar at multiple stages of the kill chain.

Quasar Initial Infection

During the initial infection stage of a Quasar compromise observed on the network of one customer, Darktrace detected a device downloading several suspicious DLL and executable (.exe) files from multiple rare external sources using the Xmlst user agent, including the executable ‘Eppzjtedzmk[.]exe’.  Analyzing this file using open-source intelligence (OSINT) suggests this is a Quasar payload, potentially indicating this represented the initial infection through DLL sideloading [3].

Interestingly, the Xmlst user agent used to download the Quasar payload has also been associated with Raccoon Stealer, an information-stealing malware that also acts as a dropper for other malware strains [4][5]. The co-occurrence of different malware components is increasingly common across the threat landscape as MaaS operating models increases in popularity, allowing attackers to employ cross-functional components from different strains.

Figure 1: Cyber AI Analyst Incident summarizing the multiple different downloads in one related incident, with technical details for the Quasar payload included. The incident event for Suspicious File Download is also linked to Possible HTTP Command and Control, suggesting escalation of activity following the initial infection.  

Quasar Establishing C2 Communication

During this phase, devices on multiple customer networks were identified making unusual external connections to the IP 193.142.146[.]212, which was not commonly seen in their networks. Darktrace analyzed the meta-properties of these SSL connections without needing to decrypt the content, to alert the usage of an unusual port not typically associated with the SSL protocol, 4782, and the usage of self-signed certificates.  Self-signed certificates do not provide any trust value and are commonly used in malware communications and ill-reputed web servers.  

Further analysis into these alerts using OSINT indicated that 193.142.146[.]212 is a Quasar C2 server and 4782 is the default port used by Quasar [6][7].  Expanding on the self-signed certificate within the Darktrace UI (see Figure 3) reveals a certificate subject and issuer of “CN=Quasar Server CA”, which is also the default self-signed certificate compiled by Quasar [6].

Figure 2: Cyber AI Analyst Incident summarizing the repeated external connections to a rare external IP that was later associated with Quasar.
Figure 3: Device Event Log of the affected device, showing Darktrace’s analysis of the SSL Certificate associated with SSL connections to 193.142.146[.]212.

A number of insights can be drawn from analysis of the Quasar C2 endpoints detected by Darktrace across multiple affected networks, suggesting a level of interoperability in the tooling used by different threat actors. In one instance, Darktrace detected a device beaconing to the endpoint ‘bittorrents[.]duckdns[.]org’ using the aforementioned “CN=Quasar Server CA” certificate. DuckDNS is a dynamic DNS service that could be abused by attackers to redirect users from their intended endpoint to malicious infrastructure, and may be shared or reused in multiple different attacks.

Figure 4: A device’s Model Event Log, showing the Quasar Server CA SSL certificate used in connections to 41.233.139[.]145 on port 5, which resolves via passive replication to ‘bittorrents[.]duckdns[.]org’.  

The sharing of malicious infrastructure among threat actors is also evident as several OSINT sources have also associated the Quasar IP 193.142.146[.]212, detected in this campaign, with different threat types.

While 193.142.146[.]212:4782 is known to be associated with Quasar, 193.142.146[.]212:8808 and 193.142.146[.]212:6606 have been associated with AsyncRAT [11], and the same IP on port 8848 has been associated with RedLineStealer [12].  Aside from the relative ease of using already developed tooling, threat actors may prefer to use open-source malware in order to avoid attribution, making the true identity of the threat actor unclear to incident responders [1][13].  

Quasar Executing Objectives

On multiple customer deployments affected by Quasar, Darktrace detected devices using BitTorrent and performing cryptocurrency mining. While these non-compliant, and potentially malicious, activities are not necessarily specific IoCs for Quasar, they do suggest that affected devices may have had greater attack surfaces than others.

For instance, one affected device was observed initiating connections to 162.19.139[.]184, a known Minergate cryptomining endpoint, and ‘zayprostofyrim[.]zapto[.]org’, a dynamic DNS endpoint linked to the Quasar Botnet by multiple OSINT vendors [9].

Figure 5: A Darktrace DETECT Event Log showing simultaneous connections to a Quasar endpoint and a cryptomining endpoint 162.19.139[.]184.

Not only does cryptocurrency mining use a significant amount of processing power, potentially disrupting an organization’s business operations and racking up high energy bills, but the software used for this mining is often written to a poor standard, thus increasing the attack surfaces of devices using them. In this instance, Quasar may have been introduced as a secondary payload from a user or attacker-initiated download of cryptocurrency mining malware.

Similarly, it is not uncommon for malicious actors to attach malware to torrented files and there were a number of examples of Darktrace detect identifying non-compliant activity, like BitTorrent connections, overlapping with connections to external locations associated with Quasar. It is therefore important for organizations to establish and enforce technical and policy controls for acceptable use on corporate devices, particularly when remote working introduces new risks.  

Figure 6: A device’s Event Log filtered by Model Breaches, showing a device connecting to BitTorrent shortly before making new or repeated connections to unusual endpoints, which were subsequently associated to Quasar.

In some cases observed by Darktrace, devices affected by Quasar were also being used to perform data exfiltration. Analysis of a period of unusual external connections to the aforementioned Quasar C2 botnet server, ‘zayprostofyrim[.]zapto[.]org’, revealed a small data upload, which may have represented the exfiltration of some data to attacker infrastructure.

Darktrace’s Autonomous Response to Quasar Attacks

On customer networks that had Darktrace RESPOND™ enabled in autonomous response mode, the threat of Quasar was mitigated and contained as soon as it was identified by DETECT. If RESPOND is not configured to respond autonomously, these actions would instead be advisory, pending manual application by the customer’s security team.

For example, following the detection of devices downloading malicious DLL and executable files, Darktrace RESPOND advised the customer to block specific connections to the relevant IP addresses and ports. However, as the device was seen attempting to download further files from other locations, RESPOND also suggested enforced a ‘pattern of life’ on the device, meaning it was only permitted to make connections that were part its normal behavior. By imposing a pattern of life, Darktrace RESPOND ensures that a device cannot perform suspicious behavior, while not disrupting any legitimate business activity.

Had RESPOND been configured to act autonomously, these mitigative actions would have been applied without any input from the customer’s security team and the Quasar compromise would have been contained in the first instance.

Figure 7: The advisory actions Darktrace RESPOND initiated to block specific connections to a malicious IP and to enforce the device’s normal patterns of life in response to the different anomalies detected on the device.

In another case, one customer affected by Quasar did have enabled RESPOND to take autonomous action, whilst also integrating it with a firewall. Here, following the detection of a device connecting to a known Quasar IP address, RESPOND initially blocked it from making connections to the IP via the customer’s firewall. However, as the device continued to perform suspicious activity after this, RESPOND escalated its response by blocking all outgoing connections from the device, effectively preventing any C2 activity or downloads.

Figure 8: RESPOND actions triggered to action via integrated firewall and TCP Resets.

Conclusion

When faced with a threat like Quasar that utilizes the infrastructure and tools of both legitimate services and other malicious malware variants, it is essential for security teams to move beyond relying on existing knowledge of attack techniques when safeguarding their network. It is no longer enough for organizations to rely on past attacks to defend against the attacks of tomorrow.

Crucially, Darktrace’s unique approach to threat detection focusses on the anomaly, rather than relying on a static list of IoCs or "known bads” based on outdated threat intelligence. In the case of Quasar, alternative or future strains of the malware that utilize different IoCs and TTPs would still be identified by Darktrace as anomalous and immediately alerted.

By learning the ‘normal’ for devices on a customer’s network, Darktrace DETECT can recognize the subtle deviations in a device’s behavior that could indicate an ongoing compromise. Darktrace RESPOND is subsequently able to follow this up with swift and targeted actions to contain the attack and prevent it from escalating further.

Credit to Nicole Wong, Cyber Analyst, Vivek Rajan Cyber Analyst

Appendices

Darktrace DETECT Model Breaches

  • Anomalous Connection / Multiple Failed Connections to Rare Endpoint
  • Anomalous Connection / Anomalous SSL without SNI to New External
  • Anomalous Connection / Application Protocol on Uncommon Port
  • Anomalous Connection / Rare External SSL Self-Signed
  • Compromise / New or Repeated to Unusual SSL Port
  • Compromise / Beaconing Activity To External Rare
  • Compromise / High Volume of Connections with Beacon Score
  • Compromise / Large Number of Suspicious Failed Connections
  • Unusual Activity / Unusual External Activity

List of IoCs

IP:Port

193.142.146[.]212:4782 -Quasar C2 IP and default port

77.34.128[.]25: 8080 - Quasar C2 IP

Domain

zayprostofyrim[.]zapto[.]org - Quasar C2 Botnet Endpoint

bittorrents[.]duckdns[.]org - Possible Quasar C2 endpoint

Certificate

CN=Quasar Server CA - Default certificate used by Quasar

Executable

Eppzjtedzmk[.]exe - Quasar executable

IP Address

95.214.24[.]244 - Quasar C2 IP

162.19.139[.]184 - Cryptocurrency Miner IP

41.233.139[.]145[VR1] [NW2] - Possible Quasar C2 IP

MITRE ATT&CK Mapping

Command and Control

T1090.002: External Proxy

T1071.001: Web Protocols

T1571: Non-Standard Port

T1001: Data Obfuscation

T1573: Encrypted Channel

T1071: Application Layer Protocol

Resource Development

T1584: Compromise Infrastructure

References

[1] https://thehackernews.com/2023/10/quasar-rat-leverages-dll-side-loading.html

[2] https://symantec-enterprise-blogs.security.com/blogs/threat-intelligence/cicada-apt10-japan-espionage

[3]https://www.virustotal.com/gui/file/bd275a1f97d1691e394d81dd402c11aaa88cc8e723df7a6aaf57791fa6a6cdfa/community

[4] https://twitter.com/g0njxa/status/1691826188581298389

[5] https://www.linkedin.com/posts/grjk83_raccoon-stealer-announce-return-after-hiatus-activity-7097906612580802560-1aj9

[6] https://community.netwitness.com/t5/netwitness-community-blog/using-rsa-netwitness-to-detect-quasarrat/ba-p/518952

[7] https://www.cisa.gov/news-events/analysis-reports/ar18-352a

[8]https://any.run/report/6cf1314c130a41c977aafce4585a144762d3fb65f8fe493e836796b989b002cb/7ac94b56-7551-4434-8e4f-c928c57327ff

[9] https://threatfox.abuse.ch/ioc/891454/

[10] https://www.virustotal.com/gui/ip-address/41.233.139.145/relations

[11] https://raw.githubusercontent.com/stamparm/maltrail/master/trails/static/malware/asyncrat.txt

[12] https://sslbl.abuse.ch/ssl-certificates/signature/RedLineStealer/

[13] https://www.botconf.eu/botconf-presentation-or-article/hunting-the-quasar-family-how-to-hunt-a-malware-family/

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
Nicole Wong
Cyber Security 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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