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April 3, 2024

Darktrace's Investigation of Raspberry Robin Worm

Discover how Darktrace is leading the hunt for Raspberry Robin. Explore early insights and strategies in the battle against 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
Alexandra Sentenac
Cyber Analyst
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03
Apr 2024

Introduction

In the face of increasingly hardened digital infrastructures and skilled security teams, malicious actors are forced to constantly adapt their attack methods, resulting in sophisticated attacks that are designed to evade human detection and bypass traditional network security measures.  

One such example that was recently investigated by Darktrace is Raspberry Robin, a highly evasive worm malware renowned for merging existing and novel techniques, as well as leveraging both physical hardware and software, to establish a foothold within organization’s networks and propagate additional malicious payloads.

What is Raspberry Robin?

Raspberry Robin, also known as ‘QNAP worm’, is a worm malware that was initially discovered at the end of 2023 [1], however, its debut in the threat landscape may have predated this, with Microsoft uncovering malicious artifacts linked to this threat (which it tracks under the name Storm-0856) dating back to 2019 [4]. At the time, little was known regarding Raspberry Robin’s objectives or operators, despite the large number of successful infections worldwide. While the identity of the actors behind Raspberry Robin still remains a mystery, more intelligence has been gathered about the malware and its end goals as it was observed delivering payloads from different malware families.

Who does Raspberry Robin target?

While it was initially reported that Raspberry Robin primarily targeted the technology and manufacturing industries, researchers discovered that the malware had actually targeted multiple sectors [3] [4]. Darktrace’s own investigations echoed this, with Raspberry Robin infections observed across various industries, including public administration, finance, manufacturing, retail education and transportation.

How does Raspberry Robin work?

Initially, it appeared that Raspberry Robin's access to compromised networks had not been utilized to deliver final-stage malware payloads, nor to steal corporate data. This uncertainty led researchers to question whether the actors involved were merely “cybercriminals playing around” or more serious threats [3]. This lack of additional exploitation was indeed peculiar, considering that attackers could easily escalate their attacks, given Raspberry Robin’s ability to bypass User Account Control using legitimate Windows tools [4].

However, at the end of July 2022, some clarity emerged regarding the operators' end goals. Microsoft researchers revealed that the access provided by Raspberry Robin was being utilized by an access broker tracked as DEV-0206 to distribute the FakeUpdates malware downloader [2]. Researchers further discovered malicious activity associated with Evil Corp TTPs (i.e., DEV-0243) [5] and payloads from the Fauppod malware family leveraging Raspberry Robin’s access [8]. This indicates that Raspberry Robin may, in fact, be an initial access broker, utilizing its presence on hundreds of infected networks to distribute additional payloads for paying malware operators. Thus far, Raspberry Robin has been observed distributing payloads linked to FIN11, Clop Gang, BumbleBee, IcedID, and TrueBot on compromised networks [12].

Raspberry Robin’s Continued Evolution

Since it first appeared in the wild, Raspberry Robin has evolved from "being a widely distributed worm with no observed post-infection actions [...] to one of the largest malware distribution platforms currently active" [8]. The fact that Raspberry Robin has become such a prevalent threat is likely due to the continual addition of new features and evasion capabilities to their malware [6] [7].  

Since its emergence, the malware has “changed its communication method and lateral movement” [6] in order to evade signature detections based on threat intelligence and previous versions. Endpoint security vendors commonly describe it as heavily obfuscated malware, employing multiple layers of evasion techniques to hinder detection and analysis. These include for example dropping a fake payload when analyzed in a sandboxed environment and using mixed-case executing commands, likely to avoid case-sensitive string-based detections.  

In more recent campaigns, Raspberry Robin further appears to have added a new distribution method as it was observed being downloaded from archive files sent as attachments using the messaging service Discord [11]. These attachments contained a legitimate and signed Windows executable, often abused by attackers for side-loading, alongside a malicious dynamic-link library (DLL) containing a Raspberry Robin sample.

Another reason for the recent success of the malware may be found in its use of one-day exploits. According to researchers, Raspberry Robin now utilizes several local privilege escalation exploits that had been recently disclosed, even before a proof of concept had been made available [9] [10]. This led cyber security professionals to believe that operators of the malware may have access to an exploit seller [6]. The use of these exploits enhances Raspberry Robin's detection evasion and persistence capabilities, enabling it to propagate on networks undetected.

Darktrace’s Coverage of Raspberry Robin

Through two separate investigations carried out by Darktrace’s Threat Research team, first in late 2022 and then in November 2023, it became evident that Raspberry Robin was capable of integrating new functionalities and tactics, techniques and procedures (TTPs) into its attacks. Darktrace DETECT™ provided full visibility over the evolving campaign activity, allowing for a comparison of the threat across both investigations. Additionally, if Darktrace RESPOND™ was enabled on affected networks, it was able to quickly mitigate and contain emerging activity during the initial stages, thwarting the further escalation of attacks.

Raspberry Robin Initial Infection

The most prevalent initial infection vector appears to be the introduction of an infected external drive, such as a USB stick, containing a malicious .LNK file (i.e., a Windows shortcut file) disguised as a thumb drive or network share. When clicked, the LNK file automatically launches cmd.exe to execute the malicious file stored on the external drive, and msiexec.exe to connect to a Raspberry Robin command-and-control (C2) endpoint and download the main malware component. The whole process leverages legitimate Windows processes and is therefore less likely to raise any alarms from more traditional security solutions. However, Darktrace DETECT was able to identify the use of Msiexec to connect to a rare endpoint as anomalous in every case investigated.

Little is currently known regarding how the external drives are infected and distributed, but it has been reported that affected USB drives had previously been used for printing at printing and copying shops, suggesting that the infection may have originated from such stores [13].

A method as simple as leaving an infected USB on a desk in a public location can be a highly effective social engineering tactic for attackers. Exploiting both curiosity and goodwill, unsuspecting individuals may innocently plug in a found USB, hoping to identify its owner, unaware that they have unwittingly compromised their device.

As Darktrace primarily operates on the network layer, the insertion of a USB endpoint device would not be within its visibility. Nevertheless, Darktrace did observe several instances wherein multiple Microsoft endpoints were contacted by compromised devices prior to the first connection to a Raspberry Robin domain. For example, connections to the URI '/fwlink/?LinkID=252669&clcid=0x409' were observed in multiple customer environments prior to the first Raspberry Robin external connection. This connectivity seems to be related to Windows attempting to retrieve information about installed hardware, such as a printer, and could also be related to the inserting of an external USB drive.

Figure 1: Device Event Log showing an affected device making connections to Microsoft endpoints, prior to contacting the Raspberry Robin C2 endpoint ‘vqdn[.]net’.
Figure 1: Device Event Log showing an affected device making connections to Microsoft endpoints, prior to contacting the Raspberry Robin C2 endpoint ‘vqdn[.]net’.

Raspberry Robin Command-and-Control Activity

In all cases investigated by Darktrace, compromised devices were detected making HTTP GET connections via the unusual port 8080 to Raspberry Robin C2 endpoints using the new user agent 'Windows Installer'.

The C2 hostnames observed were typically short and matched the regex /[a-zA-Z0-9]{2,4}.[a-zA-Z0-9]{2,6}/, and were hosted on various top-level domains (TLD) such as ‘.rocks’, ‘.pm’, and ‘.wf’. On one customer network, Darktrace observed the download of an MSI file from the Raspberry Robin domain ‘wak[.]rocks’. This package contained a heavily protected malicious DLL file whose purpose was unknown at the time.  

However, in September 2022, external researchers revealed that the main purpose of this DLL was to download further payloads and enable lateral movement, persistence and privilege escalation on compromised devices, as well as exfiltrating sensitive information about the device. As worm infections spread through networks automatically, exfiltrating device data is an essential process for threat actor to keep track of which systems have been infected.

On affected networks investigated by Darktrace, compromised devices were observed making C2 connections that contained sensitive device information, including hostnames and credentials, with additional host information likely found within the data packets [12].

Figure 2: Model Breach Event Log displaying the events that triggered the the ‘New User Agent and Suspicious Request Data’ DETECT model breach.
Figure 2: Model Breach Event Log displaying the events that triggered the the ‘New User Agent and Suspicious Request Data’ DETECT model breach.

As for C2 infrastructure, Raspberry Robin leverages compromised Internet of Things (IoT) devices such as QNAP network attached storage (NAS) systems with hijacked DNS settings [13]. NAS devices are data storage servers that provide access to the files they store from anywhere in the world. These features have been abused by Raspberry Robin operators to distribute their malicious payloads, as any uploaded file could be stored and shared easily using NAS features.

However, Darktrace found that QNAP servers are not the only devices being exploited by Raspberry Robin, with DETECT identifying other IoT devices being used as C2 infrastructure, including a Cerio wireless access point in one example. Darktrace recognized that this connection was new to the environment and deemed it as suspicious, especially as it also used new software and an unusual port for the HTTP protocol (i.e., 8080 rather than 80).

In several instances, Darktrace observed Raspberry Robin utilizing TOR exit notes as backup C2 infrastructure, with compromised devices detected connecting to TOR endpoints.

Figure 3: Raspberry Robin C2 endpoint when viewed in a sandbox environment.
Figure 3: Raspberry Robin C2 endpoint when viewed in a sandbox environment.
Figure 4: Raspberry Robin C2 endpoint when viewed in a sandbox environment.
Figure 4: Raspberry Robin C2 endpoint when viewed in a sandbox environment.

Raspberry Robin in 2022 vs 2023

Despite the numerous updates and advancements made to Raspberry Robin between the investigations carried out in 2022 and 2023, Darktrace’s detection of the malware was largely the same.

DETECT models breached during first investigation at the end of 2022:

  • Device / New User Agent
  • Anomalous Server Activity / New User Agent from Internet Facing System
  • Device / New User Agent and New IP
  • Compromise / Suspicious Request Data
  • Compromise / Uncommon Tor Usage
  • Possible Tor Usage

DETECT models breached during second investigation in late 2023:

  • Device / New User Agent and New IP
  • Device / New User Agent and Suspicious Request Data
  • Device / New User Agent
  • Device / Suspicious Domain
  • Possible Tor Usage

Darktrace’s anomaly-based approach to threat detection enabled it to consistently detect the TTPs and IoCs associated with Raspberry Robin across the two investigations, despite the operator’s efforts to make it stealthier and more difficult to analyze.

In the first investigation in late 2022, Darktrace detected affected devices downloading addition executable (.exe) files following connections to the Raspberry Robin C2 endpoint, including a numeric executable file that appeared to be associated with the Vidar information stealer. Considering the advanced evasion techniques and privilege escalation capabilities of Raspberry Robin, early detection is key to prevent the malware from downloading additional malicious payloads.

In one affected customer environment investigated in late 2023, a total of 12 devices were compromised between mid-September and the end of October. As this particular customer did not have Darktrace RESPOND, the Raspberry Robin infection was able to spread through the network unabated until the customer acted upon Darktrace DETECT’s alerts.

Had Darktrace RESPOND been enabled in autonomous response mode, it would have been able to take immediate action following the first observed connection to a Raspberry Robin C2 endpoint, by blocking connections to the suspicious endpoint and enforcing a device’s normal ‘pattern of life’.

By enforcing a pattern of life on an affected device, RESPOND would prevent it from carrying out any activity that deviates from this learned pattern, including connections to new endpoints using new software as was the case in Figure 5, effectively shutting down the attack in the first instance.

Model Breach Event Log showing RESPOND’s actions against connections to Raspberry Robin C2 endpoints.
Figure 5: Model Breach Event Log showing RESPOND’s actions against connections to Raspberry Robin C2 endpoints.

Conclusion

Raspberry Robin is a highly evasive and adaptable worm known to evolve and change its TTPs on a regular basis in order to remain undetected on target networks for as long as possible. Due to its ability to drop additional malware variants onto compromised devices, it is crucial for organizations and their security teams to detect Raspberry Robin infections at the earliest possible stage to prevent the deployment of potentially disruptive secondary attacks.

Despite its continued evolution, Darktrace's detection of Raspberry Robin remained largely unchanged across the two investigations. Rather than relying on previous IoCs or leveraging existing threat intelligence, Darktrace DETECT’s anomaly-based approach allows it to identify emerging compromises by detecting the subtle deviations in a device’s learned behavior that would typically come with a malware compromise.

By detecting the attacks at an early stage, Darktrace gave its customers full visibility over malicious activity occurring on their networks, empowering them to identify affected devices and remove them from their environments. In cases where Darktrace RESPOND was active, it would have been able to take autonomous follow-up action to halt any C2 communication and prevent the download of any additional malicious payloads.  

Credit to Alexandra Sentenac, Cyber Analyst, Trent Kessler, Senior Cyber Analyst, Victoria Baldie, Director of Incident Management

Appendices

Darktrace DETECT Model Coverage

Device / New User Agent and New IP

Device / New User Agent and Suspicious Request Data

Device / New User Agent

Compromise / Possible Tor Usage

Compromise / Uncommon Tor Usage

MITRE ATT&CK Mapping

Tactic - Technique

Command & Control - T1090.003 Multi-hop Proxy

Lateral Movement - T1210 Exploitation of remote services

Exfiltration over C2 Data - T1041 Exfiltration over C2 Channel

Data Obfuscation - T1001 Data Obfuscation

Vulnerability Scanning - T1595.002 Vulnerability Scanning

Non-Standard Port - T1571 Non-Standard Port

Persistence - T1176 Browser Extensions

Initial Access - T1189 Drive By Compromise / T1566.002  Spearphishing Link

Collection - T1185 Man in the browser

List of IoCs

IoC - Type - Description + Confidence

vqdn[.]net - Hostname - C2 Server

mwgq[.]net - Hostname - C2 Server

wak[.]rocks - Hostname - C2 Server

o7car[.]com - Hostname - C2 Server

6t[.]nz - Hostname - C2 Server

fcgz[.]net - Hostname - Possible C2 Server

d0[.]wf - Hostname - C2 Server

e0[.]wf - Hostname - C2 Server

c4z[.]pl - Hostname - C2 Server

5g7[.]at - Hostname - C2 Server

5ap[.]nl - Hostname - C2 Server

4aw[.]ro - Hostname - C2 Server

0j[.]wf - Hostname - C2 Server

f0[.]tel - Hostname - C2 Server

h0[.]pm - Hostname - C2 Server

y0[.]pm - Hostname - C2 Server

5qy[.]ro - Hostname - C2 Server

g3[.]rs - Hostname - C2 Server

5qe8[.]com - Hostname - C2 Server

4j[.]pm - Hostname - C2 Server

m0[.]yt - Hostname - C2 Server

zk4[.]me - Hostname - C2 Server

59.15.11[.]49 - IP address - Likely C2 Server

82.124.243[.]57 - IP address - C2 Server

114.32.120[.]11 - IP address - Likely C2 Server

203.186.28[.]189 - IP address - Likely C2 Server

70.124.238[.]72 - IP address - C2 Server

73.6.9[.]83 - IP address - Likely C2 Server

References

[1] https://redcanary.com/blog/raspberry-robin/  

[2] https://www.bleepingcomputer.com/news/security/microsoft-links-raspberry-robin-malware-to-evil-corp-attacks/

[3] https://7095517.fs1.hubspotusercontent-na1.net/hubfs/7095517/FLINT%202022-016%20-%20QNAP%20worm_%20who%20benefits%20from%20crime%20(1).pdf

[4] https://www.bleepingcomputer.com/news/security/microsoft-finds-raspberry-robin-worm-in-hundreds-of-windows-networks/

[5] https://therecord.media/microsoft-ties-novel-raspberry-robin-malware-to-evil-corp-cybercrime-syndicate

[6] https://securityaffairs.com/158969/malware/raspberry-robin-1-day-exploits.html

[7] https://research.checkpoint.com/2024/raspberry-robin-keeps-riding-the-wave-of-endless-1-days/

[8] https://redmondmag.com/articles/2022/10/28/microsoft-details-threat-actors-leveraging-raspberry-robin-worm.aspx

[9] https://www.bleepingcomputer.com/news/security/raspberry-robin-malware-evolves-with-early-access-to-windows-exploits/

[10] https://www.bleepingcomputer.com/news/security/raspberry-robin-worm-drops-fake-malware-to-confuse-researchers/

[11] https://thehackernews.com/2024/02/raspberry-robin-malware-upgrades-with.html

[12] https://decoded.avast.io/janvojtesek/raspberry-robins-roshtyak-a-little-lesson-in-trickery/

[13] https://blog.bushidotoken.net/2023/05/raspberry-robin-global-usb-malware.html

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
Alexandra Sentenac
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

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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
Your data. Our AI.
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