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December 4, 2025

Atomic Stealer: Darktrace’s Investigation of a Growing macOS Threat

Atomic Stealer is rapidly emerging as a significant macOS threat, using infostealing and backdoor capabilities to target Apple users worldwide. Darktrace observed campaigns in 24 countries, detecting activity across multiple kill chain stages and providing recommended actions to contain attacks.
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
Isabel Evans
Cyber Analyst
Atomic Stealer: Darktrace’s Investigation of a Growing macOS ThreatDefault blog image
04
Dec 2025

The Rise of Infostealers Targeting Apple Users

In a threat landscape historically dominated by Windows-based threats, the growing prevalence of macOS information stealers targeting Apple users is becoming an increasing concern for organizations. Infostealers are a type of malware designed to steal sensitive data from target devices, often enabling attackers to extract credentials and financial data for resale or further exploitation. Recent research identified infostealers as the largest category of new macOS malware, with an alarming 101% increase in the last two quarters of 2024 [1].

What is Atomic Stealer?

Among the most notorious is Atomic macOS Stealer (or AMOS), first observed in 2023. Known for its sophisticated build, Atomic Stealer can exfiltrate a wide range of sensitive information including keychain passwords, cookies, browser data and cryptocurrency wallets.

Originally marketed on Telegram as a Malware-as-a-Service (MaaS), Atomic Stealer has become a popular malware due to its ability to target macOS. Like other MaaS offerings, it includes services like a web panel for managing victims, with reports indicating a monthly subscription cost between $1,000 and $3,000 [2]. Although Atomic Stealer’s original intent was as a standalone MaaS product, its unique capability to target macOS has led to new variants emerging at an unprecedented rate

Even more concerning, the most recent variant has now added a backdoor for persistent access [3]. This backdoor presents a significant threat, as Atomic Stealer campaigns are believed to have reached an around 120 countries. The addition of a backdoor elevates Atomic Stealer to the rare category of backdoor deployments potentially at a global scale, something only previously attributed to nation-state threat actors [4].

This level of sophistication is also evident in the wide range of distribution methods observed since its first appearance; including fake application installers, malvertising and terminal command execution via the ClickFix technique. The ClickFix technique is particularly noteworthy: once the malware is downloaded onto the device, users are presented with what appears to be a legitimate macOS installation prompt. In reality, however, the user unknowingly initiates the execution of the Atomic Stealer malware.

This blog will focus on activity observed across multiple Darktrace customer environments where Atomic Stealer was detected, along with several indicators of compromise (IoCs). These included devices that successfully connected to endpoints associated with Atomic Stealer, those that attempted but failed to establish connections, and instances suggesting potential data exfiltration activity.

Darktrace’s Coverage of Atomic Stealer

As this evolving threat began to spread across the internet in June 2025, Darktrace observed a surge in Atomic Stealer activity, impacting numerous customers in 24 different countries worldwide. Initially, most of the cases detected in 2025 affected Darktrace customers within the Europe, Middle East, and Africa (EMEA) region. However, later in the year, Darktrace began to observe a more even distribution of cases across EMEA, the Americas (AMS), and Asia Pacific (APAC). While multiple sectors were impacted by Atomic Stealer, Darktrace customers in the education sector were the most affected, particularly during September and October, coinciding with the return to school and universities after summer closures. This spike likely reflects increased device usage as students returned and reconnected potentially compromised devices to school and campus environments.

Starting from June, Darktrace detected multiple events of suspicious HTTP activity to external connections to IPs in the range 45.94.47.0/24. Investigation by Darktrace’s Threat Research team revealed several distinct patterns ; HTTP POST requests to the URI “/contact”, identical cURL User Agents and HTTP requests to “/api/tasks/[base64 string]” URIs.

Within one observed customer’s environment in July, Darktrace detected two devices making repeated initiated HTTP connections over port 80 to IPs within the same range. The first, Device A, was observed making GET requests to the IP 45.94.47[.]158 (AS60781 LeaseWeb Netherlands B.V.), targeting the URI “/api/tasks/[base64string]” using the “curl/8.7.2” user agent. This pattern suggested beaconing activity and triggered the ‘Beaconing Activity to External Rare' model alert in Darktrace / NETWORK, with Device A’s Model Event Log showing repeated connections. The IP associated with this endpoint has since been flagged by multiple open-source intelligence (OSINT) vendors as being associated with Atomic Stealer [5].

Darktrace’s detection of Device A showing repeated connections to the suspicious IP address over port 80, indicative of beaconing behavior.
Figure 1: Darktrace’s detection of Device A showing repeated connections to the suspicious IP address over port 80, indicative of beaconing behavior.

Darktrace’s Cyber AI Analyst subsequently launched an investigation into the activity, uncovering that the GET requests resulted in a ‘503 Service Unavailable’ response, likely indicating that the server was temporarily unable to process the requests.

Cyber AI Analyst Incident showing the 503 Status Code, indicating that the server was temporarily unavailable.
Figure 2: Cyber AI Analyst Incident showing the 503 Status Code, indicating that the server was temporarily unavailable.

This unusual activity prompted Darktrace’s Autonomous Response capability to recommend several blocking actions for the device in an attempt to stop the malicious activity. However, as the customer’s Autonomous Response configuration was set to Human Confirmation Mode, Darktrace was unable to automatically apply these actions. Had Autonomous Response been fully enabled, these connections would have been blocked, likely rendering the malware ineffective at reaching its malicious command-and-control (C2) infrastructure.

Autonomous Response’s suggested actions to block suspicious connectivity on Device A in the first customer environment.
Figure 3: Autonomous Response’s suggested actions to block suspicious connectivity on Device A in the first customer environment.

In another customer environment in August, Darktrace detected similar IoCs, noting a device establishing a connection to the external endpoint 45.94.47[.]149 (ASN: AS57043 Hostkey B.V.). Shortly after the initial connections, the device was observed making repeated requests to the same destination IP, targeting the URI /api/tasks/[base64string] with the user agent curl/8.7.1, again suggesting beaconing activity. Further analysis of this endpoint after the fact revealed links to Atomic Stealer in OSINT reporting [6].

Cyber AI Analyst investigation finding a suspicious URI and user agent for the offending device within the second customer environment.
Figure 4:  Cyber AI Analyst investigation finding a suspicious URI and user agent for the offending device within the second customer environment.

As with the customer in the first case, had Darktrace’s Autonomous Response been properly configured on the customer’s network, it would have been able to block connectivity with 45.94.47[.]149. Instead, Darktrace suggested recommended actions that the customer’s security team could manually apply to help contain the attack.

Autonomous Response’s suggested actions to block suspicious connectivity to IP 45.94.47[.]149 for the device within the second customer environment.
Figure 5: Autonomous Response’s suggested actions to block suspicious connectivity to IP 45.94.47[.]149 for the device within the second customer environment.

In the most recent case observed by Darktrace in October, multiple instances of Atomic Stealer activity were seen across one customer’s environment, with two devices communicating with Atomic Stealer C2 infrastructure. During this incident, one device was observed making an HTTP GET request to the IP 45.94.47[.]149 (ASN: AS60781 LeaseWeb Netherlands B.V.). These connections targeted the URI /api/tasks/[base64string, using the user agent curl/8.7.1.  

Shortly afterward, the device began making repeated connections over port 80 to the same external IP, 45.94.47[.]149. This activity continued for several days until Darktrace detected the device making an HTTP POST request to a new IP, 45.94.47[.]211 (ASN: AS57043 Hostkey B.V.), this time targeting the URI /contact, again using the curl/8.7.1 user agent. Similar to the other IPs observed in beaconing activity, OSINT reporting later linked this one to information stealer C2 infrastructure [7].

Darktrace’s detection of suspicious beaconing connectivity with the suspicious IP 45.94.47.211.
Figure 6: Darktrace’s detection of suspicious beaconing connectivity with the suspicious IP 45.94.47.211.

Further investigation into this customer’s network revealed that similar activity had been occurring as far back as August, when Darktrace detected data exfiltration on a second device. Cyber AI Analyst identified this device making a single HTTP POST connection to the external IP 45.94.47[.]144, another IP with malicious links [8], using the user agent curl/8.7.1 and targeting the URI /contact.

Cyber AI Analyst investigation finding a successful POST request to 45.94.47[.]144 for the device within the third customer environment.
Figure 7:  Cyber AI Analyst investigation finding a successful POST request to 45.94.47[.]144 for the device within the third customer environment.

A deeper investigation into the technical details within the POST request revealed the presence of a file named “out.zip”, suggesting potential data exfiltration.

Advanced Search log in Darktrace / NETWORK showing “out.zip”, indicating potential data exfiltration for a device within the third customer environment.
Figure 8: Advanced Search log in Darktrace / NETWORK showing “out.zip”, indicating potential data exfiltration for a device within the third customer environment.

Similarly, in another environment, Darktrace was able to collect a packet capture (PCAP) of suspected Atomic Stealer activity, which revealed potential indicators of data exfiltration. This included the presence of the “out.zip” file being exfiltrated via an HTTP POST request, along with data that appeared to contain details of an Electrum cryptocurrency wallet and possible passwords.

Read more about Darktrace’s full deep dive into a similar case where this tactic was leveraged by malware as part of an elaborate cryptocurrency scam.

PCAP of an HTTP POST request showing the file “out.zip” and details of Electrum Cryptocurrency wallet.
Figure 9: PCAP of an HTTP POST request showing the file “out.zip” and details of Electrum Cryptocurrency wallet.

Although recent research attributes the “out.zip” file to a new variant named SHAMOS [9], it has also been linked more broadly to Atomic Stealer [10]. Indeed, this is not the first instance where Darktrace has seen the “out.zip” file in cases involving Atomic Stealer either. In a previous blog detailing a social engineering campaign that targeted cryptocurrency users with the Realst Stealer, the macOS version of Realst contained a binary that was found to be Atomic Stealer, and similar IoCs were identified, including artifacts of data exfiltration such as the “out.zip” file.

Conclusion

The rapid rise of Atomic Stealer and its ability to target macOS marks a significant shift in the threat landscape and should serve as a clear warning to Apple users who were traditionally perceived as more secure in a malware ecosystem historically dominated by Windows-based threats.

Atomic Stealer’s growing popularity is now challenging that perception, expanding its reach and accessibility to a broader range of victims. Even more concerning is the emergence of a variant embedded with a backdoor, which is likely to increase its appeal among a diverse range of threat actors. Darktrace’s ability to adapt and detect new tactics and IoCs in real time delivers the proactive defense organizations need to protect themselves against emerging threats before they can gain momentum.

Credit to Isabel Evans (Cyber Analyst), Dylan Hinz (Associate Principal Cyber Analyst)
Edited by Ryan Traill (Analyst Content Lead)

Appendices

References

1.     https://www.scworld.com/news/infostealers-targeting-macos-jumped-by-101-in-second-half-of-2024

2.     https://www.kandji.io/blog/amos-macos-stealer-analysis

3.     https://www.broadcom.com/support/security-center/protection-bulletin/amos-stealer-adds-backdoor

4.     https://moonlock.com/amos-backdoor-persistent-access

5.     https://www.virustotal.com/gui/ip-address/45.94.47.158/detection

6.     https://www.trendmicro.com/en_us/research/25/i/an-mdr-analysis-of-the-amos-stealer-campaign.html

7.     https://www.virustotal.com/gui/ip-address/45.94.47.211/detection

8.     https://www.virustotal.com/gui/ip-address/45.94.47.144/detection

9.     https://securityaffairs.com/181441/malware/over-300-entities-hit-by-a-variant-of-atomic-macos-stealer-in-recent-campaign.html

10.   https://binhex.ninja/malware-analysis-blogs/amos-stealer-atomic-stealer-malware.html

Darktrace Model Detections

Darktrace / NETWORK

  • Compromise / Beaconing Activity To External Rare
  • Compromise / HTTP Beaconing to New IP
  • Compromise / HTTP Beaconing to Rare Destination
  • Anomalous Connection / New User Agent to IP Without Hostname
  • Device / New User Agent
  • Compromise / Sustained TCP Beaconing Activity To Rare Endpoint
  • Compromise / Slow Beaconing Activity To External Rare
  • Anomalous Connection / Posting HTTP to IP Without Hostname
  • Compromise / Quick and Regular Windows HTTP Beaconing

Autonomous Response

  • Antigena / Network / Significant Anomaly::Antigena Alerts Over Time Block
  • Antigena / Network / Significant Anomaly::Antigena Significant Anomaly from Client Block
  • Antigena / Network / External Threat::Antigena Suspicious Activity Block

List of IoCs

  • 45.94.47[.]149 – IP – Atomic C2 Endpoint
  • 45.94.47[.]144 – IP – Atomic C2 Endpoint
  • 45.94.47[.]158 – IP – Atomic C2 Endpoint
  • 45.94.47[.]211 – IP – Atomic C2 Endpoint
  • out.zip - File Output – Possible ZIP file for Data Exfiltration

MITRE ATT&CK Mapping:

Tactic –Technique – Sub-Technique

Execution - T1204.002 - User Execution: Malicious File

Credential Access - T1555.001 - Credentials from Password Stores: Keychain

Credential Access - T1555.003 - Credentials from Web Browsers

Command & Control - T1071 - Application Layer Protocol

Exfiltration - T1041 - Exfiltration Over C2 Channel

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
Isabel Evans
Cyber Analyst

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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

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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