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November 20, 2025

Xillen Stealer Updates to Version 5 to Evade AI Detection

Xillen Stealer v4/v5 introduces advanced features to evade AI detection, steal credentials, cryptocurrency, and sensitive data across browsers, password managers, and cloud environments. With polymorphic engines, container persistence, and behavioral mimicking, this Python-based malware highlights evolving threats and future AI integration in cybercrime campaigns.
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
Tara Gould
Malware Research Lead
xillen stealer updates to version 5 to evade ai detectionDefault blog image
20
Nov 2025

Introduction

Python-based information stealer “Xillen Stealer” has recently released versions 4 and 5, expanding its targeting and functionality. The cross-platform infostealer, originally reported by Cyfirma in September 2025, targets sensitive data including credentials, cryptocurrency wallets, system information, browser data and employs anti-analysis techniques.  

The update to v4/v5 includes significantly more functionality, including:

  • Persistence
  • Ability to steal credentials from password managers, social media accounts, browser data (history, cookies and passwords) from over 100 browsers, cryptocurrency from over 70 wallets
  • Kubernetes configs and secrets
  • Docker scanning
  • Encryption
  • Polymorphism
  • System hooks
  • Peer-to-Peer (P2P) Command-and-Control (C2)
  • Single Sign-On (SSO) collector
  • Time-Based One-Time Passwords (TOTP) and biometric collection
  • EDR bypass
  • AI evasion
  • Interceptor for Two-Factor Authentication (2FA)
  • IoT scanning
  • Data exfiltration via Cloud APIs

Xillen Stealer is marketed on Telegram, with different licenses available for purchase. Users who deploy the malware have access to a professional-looking GUI that enables them to view exfiltrated data, logs, infections, configurations and subscription information.

Screenshot of the Xillen Stealer portal.
Figure 1: Screenshot of the Xillen Stealer portal.

Technical analysis

The following technical analysis examines some of the interesting functions of Xillen Stealer v4 and v5. The main functionality of Xillen Stealer is to steal cryptocurrency, credentials, system information, and account information from a range of stores.

Xillen Stealer specifically targets the following wallets and browsers:

AITargetDectection

Screenshot of Xillen Stealer’s AI Target detection function.
Figure 2: Screenshot of Xillen Stealer’s AI Target detection function.

The ‘AITargetDetection’ class is intended to use AI to detect high-value targets based on weighted indicators and relevant keywords defined in a dictionary. These indicators include “high value targets”, like cryptocurrency wallets, banking data, premium accounts, developer accounts, and business emails. Location indicators include high-value countries such as the United States, United Kingdom, Germany and Japan, along with cryptocurrency-friendly countries and financial hubs. Wealth indicators such as keywords like CEO, trader, investor and VIP have also been defined in a dictionary but are not in use at this time, pointing towards the group’s intent to develop further in the future.

While the class is named ‘AITargetDetection’ and includes placeholder functions for initializing and training a machine learning model, there is no actual implementation of machine learning. Instead, the system relies entirely on rule-based pattern matching for detection and scoring. Even though AI is not actually implemented in this code, it shows how malware developers could use AI in future malicious campaigns.

Screenshot of dead code function.
Figure 3: Screenshot of dead code function.

AI Evasion

Screenshot of AI evasion function to create entropy variance.
Figure 4: Screenshot of AI evasion function to create entropy variance.

‘AIEvasionEngine’ is a module designed to help malware evade AI-based or behavior-based detection systems, such as EDRs and sandboxes. It mimics legitimate user and system behavior, injects statistical noise, randomizes execution patterns, and camouflages resource usage. Its goal is to make the malware appear benign to machine learning detectors. The techniques used to achieve this are:

  • Behavioral Mimicking: Simulates user actions (mouse movement, fake browser use, file/network activity)
  • Noise Injection: Performs random memory, CPU, file, and network operations to confuse behavioral classifiers
  • Timing Randomization: Introduces irregular delays and sleep patterns to avoid timing-based anomaly detection
  • Resource Camouflage: Adjusts CPU and memory usage to imitate normal apps (such as browsers, text editors)
  • API Call Obfuscation: Random system API calls and pattern changes to hide malicious intent
  • Memory Access Obfuscation: Alters access patterns and entropy to bypass ML models monitoring memory behavior

PolymorphicEngine

As part of the “Rust Engine” available in Xillen Stealer is the Polymorphic Engine. The ‘PolymorphicEngine’ struct implements a basic polymorphic transformation system designed for obfuscation and detection evasion. It uses predefined instruction substitutions, control-flow pattern replacements, and dead code injection to produce varied output. The mutate_code() method scans input bytes and replaces recognized instruction patterns with randomized alternatives, then applies control flow obfuscation and inserts non-functional code to increase variability. Additional features include string encryption via XOR and a stub-based packer.

Collectors

DevToolsCollector

Figure 5: Screenshot of Kubernetes data function.

The ‘DevToolsCollector’ is designed to collect sensitive data related to a wide range of developer tools and environments. This includes:

IDE configurations

  • VS Code, VS Code Insiders, Visual Studio
  • JetBrains: Intellij, PyCharm, WebStorm
  • Sublime
  • Atom
  • Notepad++
  • Eclipse

Cloud credentials and configurations

  • AWS
  • GCP
  • Azure
  • Digital Ocean
  • Heroku

SSH keys

Docker & Kubernetes configurations

Git credentials

Database connection information

  • HeidiSQL
  • Navicat
  • DBeaver
  • MySQL Workbench
  • pgAdmin

API keys from .env files

FTP configs

  • FileZilla
  • WinSCP
  • Core FTP

VPN configurations

  • OpenVPN
  • WireGuard
  • NordVPN
  • ExpressVPN
  • CyberGhost

Container persistence

Screenshot of Kubernetes inject function.
Figure 6: Screenshot of Kubernetes inject function.

Biometric Collector

Screenshot of the ‘BiometricCollector’ function.
Figure 7: Screenshot of the ‘BiometricCollector’ function.

The ‘BiometricCollector’ attempts to collect biometric information from Windows systems by scanning the C:\Windows\System32\WinBioDatabase directory, which stores Windows Hello and other biometric configuration data. If accessible, it reads the contents of each file, encodes them in Base64, preparing them for later exfiltration. While the data here is typically encrypted by Windows, its collection indicates an attempt to extract sensitive biometric data.

Password Managers

The ‘PasswordManagerCollector’ function attempts to steal credentials stored in password managers including, OnePass, LastPass, BitWarden, Dashlane, NordPass and KeePass. However, this function is limited to Windows systems only.

SSOCollector

The ‘SSOCollector’ class is designed to collect authentication tokens related to SSO systems. It targets three main sources: Azure Active Directory tokens stored under TokenBroker\Cache, Kerberos tickets obtained through the klist command, and Google Cloud authentication data in user configuration folders. For each source, it checks known directories or commands, reads partial file contents, and stores the results as in a dictionary. Once again, this function is limited to Windows systems.

TOTP Collector

The ‘TOTP Collector’ class attempts to collect TOTPs from:

  • Authy Desktop by locating and reading from Authy.db SQLite databases
  • Microsoft Authenticator by scanning known application data paths for stored binary files
  • TOTP-related Chrome extensions by searching LevelDB files for identifiable keywords like “gauth” or “authenticator”.

Each method attempts to locate relevant files, parse or partially read their contents, and store them in a dictionary under labels like authy, microsoft_auth, or chrome_extension. However, as before, this is limited to Windows, and there is no handling for encrypted tokens.

Enterprise Collector

The ‘EnterpriseCollector’ class is used to extract credentials related to an enterprise Windows system. It targets configuration and credential data from:

  • VPN clients
    • Cisco AnyConnect, OpenVPN, Forticlient, Pulse Secure
  • RDP credentials
  • Corporate certificates
  • Active Directory tokens
  • Kerberos tickets cache

The files and directories are located based on standard environment variables with their contents read in binary mode and then encoded in Base64.

Super Extended Application Collector

The ‘SuperExtendedApplication’ Collector class is designed to scan an environment for 160 different applications on a Windows system. It iterates through the paths of a wide range of software categories including messaging apps, cryptocurrency wallets, password managers, development tools, enterprise tools, gaming clients, and security products. The list includes but is not limited to Teams, Slack, Mattermost, Zoom, Google Meet, MS Office, Defender, Norton, McAfee, Steam, Twitch, VMWare, to name a few.

Bypass

AppBoundBypass

This code outlines a framework for bypassing App Bound protections, Google Chrome' s cookie encryption. The ‘AppBoundBypass’ class attempts several evasion techniques, including memory injection, dynamic-link library (DLL) hijacking, process hollowing, atom bombing, and process doppelgänging to impersonate or hijack browser processes. As of the time of writing, the code contains multiple placeholders, indicating that the code is still in development.

Steganography

The ‘SteganographyModule’ uses steganography (hiding data within an image) to hide the stolen data, staging it for exfiltration. Multiple methods are implemented, including:

  • Image steganography: LSB-based hiding
  • NTFS Alternate Data Streams
  • Windows Registry Keys
  • Slack space: Writing into unallocated disk cluster space
  • Polyglot files: Appending archive data to images
  • Image metadata: Embedding data in EXIF tags
  • Whitespace encoding: Hiding binary in trailing spaces of text files

Exfiltration

CloudProxy

Screenshot of the ‘CloudProxy’ class.
Figure 8: Screenshot of the ‘CloudProxy’ class.

The CloudProxy class is designed for exfiltrating data by routing it through cloud service domains. It encodes the input data using Base64, attaches a timestamp and SHA-256 signature, and attempts to send this payload as a JSON object via HTTP POST requests to cloud URLs including AWS, GCP, and Azure, allowing the traffic to blend in. As of the time of writing, these public facing URLs do not accept POST requests, indicating that they are placeholders meant to be replaced with attacker-controlled cloud endpoints in a finalized build.

P2PEngine

Screenshot of the P2PEngine.
Figure 9: Screenshot of the P2PEngine.

The ‘P2PEngine’ provides multiple methods of C2, including embedding instructions within blockchain transactions (such as Bitcoin OP_RETURN, Ethereum smart contracts), exfiltrating data via anonymizing networks like Tor and I2P, and storing payloads on IPFS (a distributed file system). It also supports domain generation algorithms (DGA) to create dynamic .onion addresses for evading detection.

After a compromise, the stealer creates both HTML and TXT reports containing the stolen data. It then sends these reports to the attacker’s designated Telegram account.

Xillen Killers

 Xillen Killers.
FIgure 10: Xillen Killers.

Xillen Stealer appears to be developed by a self-described 15-year-old “pentest specialist” “Beng/jaminButton” who creates TikTok videos showing basic exploits and open-source intelligence (OSINT) techniques. The group distributing the information stealer, known as “Xillen Killers”, claims to have 3,000 members. Additionally, the group claims to have been involved in:

  • Analysis of Project DDoSia, a tool reportedly used by the NoName057(16) group, revealing that rather functioning as a distributed denial-of-service (DDos) tool, it is actually a remote access trojan (RAT) and stealer, along with the identification of involved individuals.
  • Compromise of doxbin.net in October 2025.
  • Discovery of vulnerabilities on a Russian mods site and a Ukrainian news site

The group, which claims to be part of the Russian IT scene, use Telegram for logging, marketing, and support.

Conclusion

While some components of XillenStealer remain underdeveloped, the range of intended feature set, which includes credential harvesting, cryptocurrency theft, container targeting, and anti-analysis techniques, suggests that once fully developed it could become a sophisticated stealer. The intention to use AI to help improve targeting in malware campaigns, even though not yet implemented, indicates how threat actors are likely to incorporate AI into future campaigns.  

Credit to Tara Gould (Threat Research Lead)
Edited by Ryan Traill (Analyst Content Lead)

Appendicies

Indicators of Compromise (IoCs)

395350d9cfbf32cef74357fd9cb66134 - confid.py

F3ce485b669e7c18b66d09418e979468 - stealer_v5_ultimate.py

3133fe7dc7b690264ee4f0fb6d867946 - xillen_v5.exe

https://github[.]com/BengaminButton/XillenStealer

https://github[.]com/BengaminButton/XillenStealer/commit/9d9f105df4a6b20613e3a7c55379dcbf4d1ef465

MITRE ATT&CK

ID Technique

T1059.006 - Python

T1555 - Credentials from Password Stores

T1555.003 - Credentials from Password Stores: Credentials from Web Browsers

T1555.005 - Credentials from Password Stores: Password Managers

T1649 - Steal or Forge Authentication Certificates

T1558 - Steal or Forge Kerberos Tickets

T1539 - Steal Web Session Cookie

T1552.001 - Unsecured Credentials: Credentials In Files

T1552.004 - Unsecured Credentials: Private Keys

T1552.005 - Unsecured Credentials: Cloud Instance Metadata API

T1217 - Browser Information Discovery

T1622 - Debugger Evasion

T1082 - System Information Discovery

T1497.001 - Virtualization/Sandbox Evasion: System Checks

T1115 - Clipboard Data

T1001.002 - Data Obfuscation: Steganography

T1567 - Exfiltration Over Web Service

T1657 - Financial 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
Tara Gould
Malware Research Lead

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August 11, 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

prompt injectionDefault blog imageDefault blog image

Key takeaways

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

How behavioral detection helps stop prompt injection attacks

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

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

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

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

How do prompt injection attacks work?

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

Prompt injection attack example

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

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

How we tested prompt injection attacks on an enterprise agent

Summary:

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

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

Figure 1
Figure 2

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

How Darktrace detected a prompt injection attack

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

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

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

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

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

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

Why behavioral security makes a difference detecting prompt injection attacks

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

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

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

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

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

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

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

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

Why enterprise AI security requires more than guardrails

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

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

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

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

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

That's where behavioral detection comes in.

How Darktrace detects prompt injection attacks in emails

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

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

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

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

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

How to secure enterprise AI operations from prompt injection attacks

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

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

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

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

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

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

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

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