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November 8, 2022

[Part 1] Analysis of a Raccoon Stealer v1 Infection

Darktrace’s SOC team observed a fast-paced compromise involving Raccoon Stealer v1. See which steps the Raccoon Stealer v1 took to extract company data!
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
Mark Turner
SOC Shift Supervisor
Written by
Sam Lister
Specialist Security Researcher
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08
Nov 2022

Introduction

Towards the end of March 2022, the operators of Raccoon Stealer announced the closure of the Raccoon Stealer project [1]. In May 2022, Raccoon Stealer v2 was unleashed onto the world, with huge numbers of cases being detected across Darktrace’s client base. In this series of blog posts, we will follow the development of Raccoon Stealer between March and September 2022. We will first shed light on how Raccoon Stealer functioned before its demise, by providing details of a Raccoon Stealer v1 infection which Darktrace’s SOC saw within a client network on the 18th March 2022. In the follow-up post, we will provide details about the surge in Raccoon Stealer v2 cases that Darktrace’s SOC has observed since May 2022.  

What is Raccoon Stealer?

The misuse of stolen account credentials is a primary method used by threat actors to gain initial access to target environments [2]. Threat actors have several means available to them for obtaining account credentials. They may, for example, distribute phishing emails which trick their recipients into divulging account credentials. Alternatively, however, they may install information-stealing malware (i.e, info-stealers) onto users’ devices. The results of credential theft can be devastating. Threat actors may use the credentials to gain access to an organization’s SaaS environment, or they may use them to drain users’ online bank accounts or cryptocurrency wallets. 

Raccoon Stealer is a Malware-as-a-Service (MaaS) info-stealer first publicized in April 2019 on Russian-speaking hacking forums. 

Figure 1: One of the first known mentions of Raccoon Stealer on a Russian-speaking hacking forum named ‘Hack Forums’ on the 13th April 2019

The team of individuals behind Raccoon Stealer provide a variety of services to their customers (known as ‘affiliates’), including access to the info-stealer, an easy-to-use automated backend panel, hosting infrastructure, and 24/7 customer support [3]. 

Once Raccoon Stealer affiliates gain access to the info-stealer, it is up to them to decide how to distribute it. Since 2019, affiliates have been observed distributing the info-stealer via a variety of methods, such as exploit kits, phishing emails, and fake cracked software websites [3]/[4]. Once affiliates succeed in installing Raccoon Stealer onto target systems, the info-stealer will typically seek to obtain sensitive information saved in browsers and cryptocurrency wallets. The info-stealer will then exfiltrate the stolen data to a Command and Control (C2) server. The affiliate can then use the stolen data to conduct harmful follow-up activities. 

Towards the end of March 2022, the team behind Raccoon Stealer publicly announced that they would be suspending their operations after one of their core developers was killed during the Russia-Ukraine conflict [5]. 

Figure 2: Raccoon Stealer resignation post on March 25th 2022

Recent details shared by the US Department of Justice [6]/[7] indicate that it was in fact the arrest, rather than the death, of a key Raccoon Stealer operator which led the Raccoon Stealer team to suspend their operations [8].  

The closure of the Raccoon Stealer project, which ultimately resulted from the FBI-backed dismantling of Raccoon Stealer’s infrastructure in March 2022, did not last long, with the completion of Raccoon Stealer v2 being announced on the Raccoon Stealer Telegram channel on the 17th May 2022 [9]. 

 

Figure 3: Telegram post about new version of Raccoon Stealer

In the second part of this blog series, we will provide details of the recent surge in Raccoon Stealer v2 activity. In this post, however, we will provide insight into how the old version of Raccoon Stealer functioned just before its demise, by providing details of a Raccoon Stealer v1 infection which occurred on the 18th March 2022. 

Attack Details

On the 18th March, at around 13:00 (UTC), a user’s device within a customer’s network was seen contacting several websites providing fake cracked software. 

Figure 4: The above figure — obtained from the Darktrace Event Log for the infected device — highlights its connections to cracked software websites such as ‘licensekeysfree[.]com’ and ‘hdlicense[.]com’ before contacting ‘lion-files[.]xyz’ and ‘www.mediafire[.]com’

The user’s attempt to download cracked software from one of these websites resulted in their device making an HTTP GET request with a URI string containing ‘autodesk-revit-crack-v2022-serial-number-2022’ to an external host named ‘lion-filez[.]xyz’

Figure 5: Screenshot from hdlicense[.]com around the time of the infection shows a “Download” button linking to the ‘lion-filez[.]xyz’ endpoint

The device’s HTTP GET request to lion-filez[.]xyz was immediately followed by an HTTPS connection to the file hosting service, www.mediafire[.]com. Given that threat actors are known to abuse platforms such as MediaFire and Discord CDN to host their malicious payloads, it is likely that the user’s device downloaded the Raccoon Stealer v1 sample over its HTTPS connection to www.mediafire[.]com.  

After installing the info-stealer sample, the user’s device was seen making an HTTP GET request with the URI string ‘/g_shock_casio_easy’ to 194.180.191[.]185. The endpoint responded to the request with data related to a Telegram channel named ‘G-Shock’.

Figure 6: Telegram channel ‘@g_shock_casio_easy’

The returned data included the Telegram channel’s description, which in this case, was a base64 encoded and RC4 encrypted string of characters [10]/[11]. The Raccoon Stealer sample decoded and decrypted this string of characters to obtain its C2 IP address, 188.166.49[.]196. This technique used by Raccoon Stealer v1 closely mirrors the espionage method known as ‘dead drop’ — a method in which an individual leaves a physical object such as papers, cash, or weapons in an agreed hiding spot so that the intended recipient can retrieve the object later on without having to come in to contact with the source. In this case, the operators of Raccoon Stealer ‘left’ the malware’s C2 IP address within the description of a Telegram channel. Usage of this method allowed the operators of Raccoon Stealer to easily change the malware’s C2 infrastructure.  

After obtaining the C2 IP address from the ‘G-Shock’ Telegram channel, the Raccoon Stealer sample made an HTTP POST request with the URI string ‘/’ to the C2 IP address, 188.166.49[.]196. This POST request contained a Windows GUID,  a username, and a configuration ID. These details were RC4 encrypted and base64 encoded [12]. The C2 server responded to this HTTP POST request with JSON-formatted configuration information [13], including an identifier string, URL paths for additional files, along with several other fields. This configuration information was also concealed using RC4 encryption and base64 encoding.  

Figure 7- Fields within the JSON-formatted configuration data [13]

In this case, the server’s response included the identifier string ‘hv4inX8BFBZhxYvKFq3x’, along with the following URL paths:

  • /l/f/hv4inX8BFBZhxYvKFq3x/77d765d8831b4a7d8b5e56950ceb96b7c7b0ed70
  • /l/f/hv4inX8BFBZhxYvKFq3x/0cb4ab70083cf5985b2bac837ca4eacb22e9b711
  • /l/f/hv4inX8BFBZhxYvKFq3x/5e2a950c07979c670b1553b59b3a25c9c2bb899b
  • /l/f/hv4inX8BFBZhxYvKFq3x/2524214eeea6452eaad6ea1135ed69e98bf72979

After retrieving configuration data, the user’s device was seen making HTTP GET requests with the above URI strings to the C2 server. The C2 server responded to these requests with legitimate library files such as sqlite3.dll. Raccoon Stealer uses these libraries to extract data from targeted applications. 

Once the Raccoon Stealer sample had collected relevant data, it made an HTTP POST request with the URI string ‘/’ to the C2 server. This posted data likely included a ZIP file (named with the identifier string) containing stolen credentials [13]. 

The observed infection chain, which lasted around 20 minutes, consisted of the following steps:

1. User’s device installs Raccoon Stealer v1 samples from the user attempting to download cracked software

2. User’s device obtains the info-stealer’s C2 IP address from the description text of a Telegram channel

3. User’s device makes an HTTP POST request with the URI string ‘/’ to the C2 server. The request contains a Windows GUID,  a username, and a configuration ID. The response to the request contains configuration details, including an identifier string and URL paths for additional files

4. User’s device downloads library files from the C2 server

5. User’s device makes an HTTP POST request with the URI string ‘/’ to the C2 server. The request contains stolen data

Darktrace Coverage 

Although RESPOND/Network was not enabled on the customer’s deployment, DETECT picked up on several of the info-stealer’s activities. In particular, the device’s downloads of library files from the C2 server caused the following DETECT/Network models to breach:

  • Anomalous File / Masqueraded File Transfer
  • Anomalous File / EXE from Rare External Location
  • Anomalous File / Zip or Gzip from Rare External Location
  • Anomalous File / EXE from Rare External Location
  • Anomalous File / Multiple EXE from Rare External Locations
Figure 8: Event Log for the infected device shows 'Anomalous File / Masqueraded File Transfer' model breach after the device's download of a library file from the C2 server

Since the customer was subscribed to the Darktrace Proactive Threat Notification (PTN) service, they were proactively notified of the info-stealer’s activities. The quick response by Darktrace’s 24/7 SOC team helped the customer to contain the infection and to prevent further damage from being caused. Having been alerted to the info-stealer activity by the SOC team, the customer would also have been able to change the passwords for the accounts whose credentials were exfiltrated.

If RESPOND/Network had been enabled on the customer’s deployment, then it would have blocked the device’s connections to the C2 server, which would have likely prevented any stolen data from being exfiltrated.

Conclusion

Towards the end of March 2022, the team behind Raccoon Stealer announced that they would be suspending their operations. Recent developments suggest that the arrest of a core Raccoon Stealer developer was responsible for this suspension. Just before the Raccoon Stealer team were forced to shut down, Darktrace’s SOC team observed a Raccoon Stealer infection within a client’s network. In this post, we have provided details of the network-based behaviors displayed by the observed Raccoon Stealer sample. Since these v1 samples are no longer active, the details provided here are only intended to provide historical insight into the development of Raccoon Stealer’s operations and the activities carried out by Raccoon Stealer v1 just before its demise. In the next post of this series, we will discuss and provide details of Raccoon Stealer v2 — the new and highly prolific version of Raccoon Stealer. 

Thanks to Stefan Rowe and the Threat Research Team for their contributions to this blog.

References

[1] https://twitter.com/3xp0rtblog/status/1507312171914461188

[2] https://www.gartner.com/doc/reprints?id=1-29OTFFPI&ct=220411&st=sb

[3] https://www.cybereason.com/blog/research/hunting-raccoon-stealer-the-new-masked-bandit-on-the-block

[4] https://www.cyberark.com/resources/threat-research-blog/raccoon-the-story-of-a-typical-infostealer

[5] https://www.bleepingcomputer.com/news/security/raccoon-stealer-malware-suspends-operations-due-to-war-in-ukraine/

[6] https://www.justice.gov/usao-wdtx/pr/newly-unsealed-indictment-charges-ukrainian-national-international-cybercrime-operation

[7] https://www.youtube.com/watch?v=Fsz6acw-ZJY

[8] https://riskybiznews.substack.com/p/raccoon-stealer-dev-didnt-die-in

[9] https://medium.com/s2wblog/raccoon-stealer-is-back-with-a-new-version-5f436e04b20d

[10] https://blog.cyble.com/2021/10/21/raccoon-stealer-under-the-lens-a-deep-dive-analysis/

[11] https://decoded.avast.io/vladimirmartyanov/raccoon-stealer-trash-panda-abuses-telegram/

[12] https://blogs.blackberry.com/en/2021/09/threat-thursday-raccoon-infostealer

[13] https://cyberint.com/blog/research/raccoon-stealer/

Appendices

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
Mark Turner
SOC Shift Supervisor
Written by
Sam Lister
Specialist Security Researcher

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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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