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March 23, 2023

Amadey Info Stealer and N-Day Vulnerabilities

Understand the implications of the Amadey info stealer on cybersecurity and how it exploits N-day vulnerabilities for data theft.
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
Zoe Tilsiter
Cyber Analyst
Written by
The Darktrace Threat Research Team
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23
Mar 2023

The continued prevalence of Malware as a Service (MaaS) across the cyber threat landscape means that even the most inexperienced of would-be malicious actors are able to carry out damaging and wide-spread cyber-attacks with relative ease. Among these commonly employed MaaS are information stealers, or info-stealers, a type of malware that infects a device and attempts to gather sensitive information before exfiltrating it to the attacker. Info-stealers typically target confidential information, such as login credentials and bank details, and attempt to lie low on a compromised device, allowing access to sensitive data for longer periods of time. 

It is essential for organizations to have efficient security measures in place to defend their networks from attackers in an increasing versatile and accessible threat landscape, however incident response alone is not enough. Having an autonomous decision maker able to not only detect suspicious activity, but also take action against it in real time, is of the upmost importance to defend against significant network compromise. 

Between August and December 2022, Darktrace detected the Amadey info-stealer on more than 30 customer environments, spanning various regions and industry verticals across the customer base. This shows a continual presence and overlap of info-stealer indicators of compromise (IOCs) across the cyber threat landscape, such as RacoonStealer, which we discussed last November (Part 1 and Part 2).

Background on Amadey

Amadey Bot, a malware that was first discovered in 2018, is capable of stealing sensitive information and installing additional malware by receiving commands from the attacker. Like other malware strains, it is being sold in illegal forums as MaaS starting from $500 USD [1]. 

Researchers at AhnLab found that Amadey is typically distributed via existing SmokeLoader loader malware campaigns. Downloading cracked versions of legitimate software causes SmokeLoader to inject malicious payload into Windows Explorer processes and proceeds to download Amadey.  

The botnet has also been used for distributed denial of service (DDoS) attacks, and as a vector to install malware spam campaigns, such as LockBit 3.0 [2]. Regardless of the delivery techniques, similar patterns of activity were observed across multiple customer environments. 

Amadey’s primary function is to steal information and further distribute malware. It aims to extract a variety of information from infected devices and attempts to evade the detection of security measures by reducing the volume of data exfiltration compared to that seen in other malicious instances.

Darktrace DETECT/Network™ and its built-in features, such as Wireshark Packet Captures (PCAP), identified Amadey activity on customer networks, whilst Darktrace RESPOND/Network™ autonomously intervened to halt its progress.

Attack Details

Figure 1: Timeline of Amadey info-stealer kill chain.

Initial Access  

User engagement with malicious email attachments or cracked software results in direct execution of the SmokeLoader loader malware on a device. Once the loader has executed its payload, it is then able to download additional malware, including the Amadey info-stealer.

Unusual Outbound Connections 

After initial access by the loader and download of additional malware, the Amadey info-stealer captures screenshots of network information and sends them to Amadey command and control (C2) servers via HTTP POST requests with no GET to a .php URI. An example of this can be seen in Figure 2.  

Figure 2: PCAP from an affected customer showing screenshots being sent out to the Amadey C2 server via a .jpg file. 

C2 Communications  

The infected device continues to make repeated connections out to this Amadey endpoint. Amadey's C2 server will respond with instructions to download additional plugins in the form of dynamic-link libraries (DLLs), such as "/Mb1sDv3/Plugins/cred64.dll", or attempt to download secondary info-stealers such as RedLine or RaccoonStealer. 

Internal Reconnaissance 

The device downloads executable and DLL files, or stealer configuration files to steal additional network information from software including RealVNC and Outlook. Most compromised accounts were observed downloading additional malware following commands received from the attacker.

Data Exfiltration 

The stolen information is then sent out via high volumes of HTTP connection. It makes HTTP POSTs to malicious .php URIs again, this time exfiltrating more data such as the Amadey version, device names, and any anti-malware software installed on the system.

How did the attackers bypass the rest of the security stack?

Existing N-Day vulnerabilities are leveraged to launch new attacks on customer networks and potentially bypass other tools in the security stack. Additionally, exfiltrating data via low and slow HTTP connections, rather than large file transfers to cloud storage platforms, is an effective means of evading the detection of traditional security tools which often look for large data transfers, sometimes to a specific list of identified “bad” endpoints.

Darktrace Coverage 

Amadey activity was autonomously identified by DETECT and the Cyber AI Analyst. A list of DETECT models that were triggered on deployments during this kill chain can be found in the Appendices. 

Various Amadey activities were detected and highlighted in DETECT model breaches and their model breach event logs. Figure 3 shows a compromised device making suspicious HTTP POST requests, causing the ‘Anomalous Connection / Posting HTTP to IP Without Hostname’ model to breach. It also downloaded an executable file (.exe) from the same IP.

Figure 3: Amadey activity on a customer deployment captured by model breaches and event logs. 

DETECT’s built-in features also assisted with detecting the data exfiltration. Using the PCAP integration, the exfiltrated data was captured for analysis. Figure 4 shows a connection made to the Amadey endpoint, in which information about the infected device, such as system ID and computer name, were sent. 

Figure 4: PCAP downloaded from Darktrace event logs highlighting data egress to the Amadey endpoint. 

Further information about the infected system can be seen in the above PCAP. As outlined by researchers at Ahnlab and shown in Figure 5, additional system information sent includes the Amadey version (vs=), the device’s admin privilege status (ar=), and any installed anti-malware or anti-virus software installed on the infected environment (av=) [3]. 

Figure 5: AhnLab’s glossary table explaining the information sent to the Amadey C2 server. 

Darktrace’s AI Analyst was also able to connect commonalities between model breaches on a device and present them as a connected incident made up of separate events. Figure 6 shows the AI Analyst incident log for a device having breached multiple models indicative of the Amadey kill chain. It displays the timeline of these events, the specific IOCs, and the associated attack tactic, in this case ‘Command and Control’. 

Figure 6: A screenshot of multiple IOCs and activity correlated together by AI Analyst. 

When enabled on customer’s deployments, RESPOND was able to take immediate action against Amadey to mitigate its impact on customer networks. RESPOND models that breached include: 

  • Antigena / Network / Significant Anomaly / Antigena Significant Anomaly from Client Block
  • Antigena / Network / External Threat / Antigena Suspicious File Block 
  • Antigena / Network / Significant Anomaly / Antigena Controlled and Model Breach

On one customer’s environment, a device made a POST request with no GET to URI ‘/p84Nls2/index.php’ and unepeureyore[.]xyz. RESPOND autonomously enforced a previously established pattern of life on the device twice for 30 minutes each and blocked all outgoing traffic from the device for 10 minutes. Enforcing a device’s pattern of life restricts it to conduct activity within the device and/or user’s expected pattern of behavior and blocks anything anomalous or unexpected, enabling normal business operations to continue. This response is intended to reduce the potential scale of attacks by disrupting the kill chain, whilst ensuring business disruption is kept to a minimum. 

Figure 7: RESPOND actions taken on a customer deployment to disrupt the Amadey kill chain. 

The Darktrace Threat Research team conducted thorough investigations into Amadey activity observed across the customer base. They were able to identify and contextualize this threat across the fleet, enriching AI insights with collaborative human analysis. Pivoting from AI insights as their primary source of information, the Threat Research team were able to provide layered analysis to confirm this campaign-like activity and assess the threat across multiple unique environments, providing a holistic assessment to customers with contextualized insights.

Conclusion

The presence of the Amadey info-stealer in multiple customer environments highlights the continuing prevalence of MaaS and info-stealers across the threat landscape. The Amadey info-stealer in particular demonstrates that by evading N-day vulnerability patches, threat actors routinely launch new attacks. These malicious actors are then able to evade detection by traditional security tools by employing low and slow data exfiltration techniques, as opposed to large file transfers.

Crucially, Darktrace’s AI insights were coupled with expert human analysis to detect, respond, and provide contextualized insights to notify customers of Amadey activity effectively. DETECT captured Amadey activity taking place on customer deployments, and where enabled, RESPOND’s autonomous technology was able to take immediate action to reduce the scale of such attacks. Finally, the Threat Research team were in place to provide enhanced analysis for affected customers to help security teams future-proof against similar attacks.

Appendices

Darktrace Model Detections 

Anomalous File / EXE from Rare External Location

Device / Initial Breach Chain Compromise

Anomalous Connection / Posting HTTP to IP Without Hostname 

Anomalous Connection / POST to PHP on New External Host

Anomalous Connection / Multiple HTTP POSTs to Rare Hostname 

Compromise / Beaconing Activity To External Rare

Compromise / Slow Beaconing Activity To External Rare

Anomalous Connection / Multiple Failed Connections to Rare Endpoint

List of IOCs

f0ce8614cc2c3ae1fcba93bc4a8b82196e7139f7 - SHA1 - Amadey DLL File Hash

e487edceeef3a41e2a8eea1e684bcbc3b39adb97 - SHA1 - Amadey DLL File Hash

0f9006d8f09e91bbd459b8254dd945e4fbae25d9 - SHA1 - Amadey DLL File Hash

4069fdad04f5e41b36945cc871eb87a309fd3442 - SHA1 - Amadey DLL File Hash

193.106.191[.]201 - IP - Amadey C2 Endpoint

77.73.134[.]66 - IP - Amadey C2 Endpoint

78.153.144[.]60 - IP - Amadey C2 Endpoint

62.204.41[.]252 - IP - Amadey C2 Endpoint

45.153.240[.]94 - IP - Amadey C2 Endpoint

185.215.113[.]204 - IP - Amadey C2 Endpoint

85.209.135[.]11 - IP - Amadey C2 Endpoint

185.215.113[.]205 - IP - Amadey C2 Endpoint

31.41.244[.]146 - IP - Amadey C2 Endpoint

5.154.181[.]119 - IP - Amadey C2 Endpoint

45.130.151[.]191 - IP - Amadey C2 Endpoint

193.106.191[.]184 - IP - Amadey C2 Endpoint

31.41.244[.]15 - IP - Amadey C2 Endpoint

77.73.133[.]72 - IP - Amadey C2 Endpoint

89.163.249[.]231 - IP - Amadey C2 Endpoint

193.56.146[.]243 - IP - Amadey C2 Endpoint

31.41.244[.]158 - IP - Amadey C2 Endpoint

85.209.135[.]109 - IP - Amadey C2 Endpoint

77.73.134[.]45 - IP - Amadey C2 Endpoint

moscow12[.]at - Hostname - Amadey C2 Endpoint

moscow13[.]at - Hostname - Amadey C2 Endpoint

unepeureyore[.]xyz - Hostname - Amadey C2 Endpoint

/fb73jc3/index.php - URI - Amadey C2 Endpoint

/panelis/index.php - URI - Amadey C2 Endpoint

/panelis/index.php?scr=1 - URI - Amadey C2 Endpoint

/panel/index.php - URI - Amadey C2 Endpoint

/panel/index.php?scr=1 - URI - Amadey C2 Endpoint

/panel/Plugins/cred.dll - URI - Amadey C2 Endpoint

/jg94cVd30f/index.php - URI - Amadey C2 Endpoint

/jg94cVd30f/index.php?scr=1 - URI - Amadey C2 Endpoint

/o7Vsjd3a2f/index.php - URI - Amadey C2 Endpoint

/o7Vsjd3a2f/index.php?scr=1 - URI - Amadey C2 Endpoint

/o7Vsjd3a2f/Plugins/cred64.dll - URI - Amadey C2 Endpoint

/gjend7w/index.php - URI - Amadey C2 Endpoint

/hfk3vK9/index.php - URI - Amadey C2 Endpoint

/v3S1dl2/index.php - URI - Amadey C2 Endpoint

/f9v33dkSXm/index.php - URI - Amadey C2 Endpoint

/p84Nls2/index.php - URI - Amadey C2 Endpoint

/p84Nls2/Plugins/cred.dll - URI - Amadey C2 Endpoint

/nB8cWack3/index.php - URI - Amadey C2 Endpoint

/rest/index.php - URI - Amadey C2 Endpoint

/Mb1sDv3/index.php - URI - Amadey C2 Endpoint

/Mb1sDv3/index.php?scr=1 - URI - Amadey C2 Endpoint

/Mb1sDv3/Plugins/cred64.dll  - URI - Amadey C2 Endpoint

/h8V2cQlbd3/index.php - URI - Amadey C2 Endpoint

/f5OknW/index.php - URI - Amadey C2 Endpoint

/rSbFldr23/index.php - URI - Amadey C2 Endpoint

/rSbFldr23/index.php?scr=1 - URI - Amadey C2 Endpoint

/jg94cVd30f/Plugins/cred64.dll - URI - Amadey C2 Endpoint

/mBsjv2swweP/Plugins/cred64.dll - URI - Amadey C2 Endpoint

/rSbFldr23/Plugins/cred64.dll - URI - Amadey C2 Endpoint

/Plugins/cred64.dll - URI - Amadey C2 Endpoint

Mitre Attack and Mapping 

Collection:

T1185 - Man the Browser

Initial Access and Resource Development:

T1189 - Drive-by Compromise

T1588.001 - Malware

Persistence:

T1176 - Browser Extensions

Command and Control:

T1071 - Application Layer Protocol

T1071.001 - Web Protocols

T1090.002 - External Proxy

T1095 - Non-Application Layer Protocol

T1571 - Non-Standard Port

T1105 - Ingress Tool Transfer

References 

[1] https://malpedia.caad.fkie.fraunhofer.de/details/win.amadey

[2] https://asec.ahnlab.com/en/41450/

[3] https://asec.ahnlab.com/en/36634/

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
Zoe Tilsiter
Cyber Analyst
Written by
The Darktrace Threat Research Team

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August 7, 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.

This is the approach Darktrace has taken for years: learning what is normal across an organization’s digital environment, identifying meaningful deviations, and responding to emerging threats without relying on known attack signatures. As autonomous AI agents introduce new and unpredictable behaviors, that foundation becomes increasingly important to securing the enterprise.

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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