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February 8, 2024

How CoinLoader Hijacks Networks

Discover how Darktrace decrypted the CoinLoader malware hijacking networks for cryptomining. Learn about the tactics and protection strategies employed.
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
Signe Zaharka
Principal Cyber Analyst
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08
Feb 2024

About Loader Malware

Loader malware was a frequent topic of conversation and investigation within the Darktrace Threat Research team throughout 2023, with a wide range of existing and novel variants affecting a significant number of Darktrace customers, as detailed in Darktrace’s inaugural End of Year Threat Report. The multi-phase nature of such compromises poses a significant threat to organizations due to the need to defend against multiple threats at the same time.

CoinLoader, a variant of loader malware first observed in the wild in 2018 [1], is an example of one of the more prominent variant of loaders observed by Darktrace in 2023, with over 65 customers affected by the malware. Darktrace’s Threat Research team conducted a deep dive investigation into the patterns of behavior exhibited by devices infected with CoinLoader in the latter part of 2023, with compromises observed in Europe, the Middle East and Africa (EMEA), Asia-Pacific (APAC) and the Americas.

The autonomous threat detection capabilities of Darktrace DETECT™ allowed for the effective identification of these CoinLoader infections whilst Darktrace RESPOND™, if active, was able to quickly curtail attacker’s efforts and prevent more disruptive, and potentially costly, secondary compromises from occurring.

What is CoinLoader?

Much like other strains of loader, CoinLoader typically serves as a first stage malware that allows threat actors to gain initial access to a network and establish a foothold in the environment before delivering subsequent malicious payloads, including adware, botnets, trojans or pay-per-install campaigns.

CoinLoader is generally propagated through trojanized popular software or game installation archive files, usually in the rar or zip formats. These files tend can be easily obtained via top results displayed in search engines when searching for such keywords as "crack" or "keygen" in conjunction with the name of the software the user wishes to pirate [1,2,3,4]. By disguising the payload as a legitimate programme, CoinLoader is more likely to be unknowingly downloaded by endpoint users, whilst also bypassing traditional security measures that trust the download.

It also has several additional counter-detection methods including using junk code, variable obfuscation, and encryption for shellcode and URL schemes. It relies on dynamic-link library (DLL) search order hijacking to load malicious DLLs to legitimate executable files. The malware is also capable of performing a variety of checks for anti-virus processes and disabling endpoint protection solutions.

In addition to these counter-detection tactics, CoinLoader is also able to prevent the execution of its malicious DLL files in sandboxed environments without the presence of specific DNS cache records, making it extremely difficult for security teams and researchers to analyze.

In 2020 it was reported that CoinLoader compromises were regularly seen alongside cryptomining activity and even used the alias “CoinMiner” in some cases [2]. Darktrace’s investigations into CoinLoader in 2023 largely confirmed this theory, with around 15% of observed CoinLoader connections being related to cryptomining activity.

Cryptomining malware consumes large amounts of a hijacked (or cryptojacked) device's resources to perform complex mathematical calculations and generate income for the attacker all while quietly working in the background. Cryptojacking can lead to high electricity costs, device slow down, loss of functionality, and in the worst case scenario can be a potential fire hazard.

Darktrace Coverage of CoinLoader

In September 2023, Darktrace observed several cases of CoinLoader that served to exemplify the command-and-control (C2) communication and subsequent cryptocurrency mining activities typically observed during CoinLoader compromises. While the initial infection method in these cases was outside of Darktrace’s purview, it likely occurred via socially engineered phishing emails or, as discussed earlier, trojanized software downloads.

Command-and-Control Activity

CoinLoader compromises observed across the Darktrace customer base were typically identified by encrypted C2 connections over port 433 to rare external endpoints using self-signed certificates containing "OU=IT,O=MyCompany LLC,L=San Francisco,ST=California,C=US" in their issue fields.

All observed CoinLoader C2 servers were associated with the ASN of MivoCloud, a Virtual Private Server (VPS) hosting service (AS39798 MivoCloud SRL). It had been reported that Russian-state sponsored threat actors had previously abused MivoCloud’s infrastructure in order to bypass geo-blocking measures during phishing attacks against western nations [5].

Darktrace observed that the majority of CoinLoader infrastructure utilized IP addresses in the 185.225.0.0/19 range and were associated with servers hosted in Romania, with just one instance of an IP address based in Moldova. The domain names of these servers typically followed the naming pattern ‘*[a-d]{1}[.]info’, with 'ams-updatea[.]info’, ‘ams-updateb[.]info’, ‘ams-updatec[.]info’, and ‘ams-updated[.]info’ routinely identified on affected networks.

Researchers found that CoinLoader typically uses DNS tunnelling in order to covertly exchange information with attacker-controlled infrastructure, including the domains ‘candatamsnsdn[.]info’, ‘mapdatamsnsdn[.]info’, ‘rqmetrixsdn[.]info’ [4].

While Darktrace did not observe these particular domains, it did observer similar DNS lookups to a similar suspicous domain, namely ‘ucmetrixsdn[.]info’, in addition to the aforementioned HTTPS C2 connections.

Cryptomining Activity and Possible Additional Tooling

After establishing communication channels with CoinLoader servers, affected devices were observed carrying out a range of cryptocurrency mining activities. Darktrace detected devices connecting to multiple MivoCloud associated IP addresses using the MinerGate protocol alongside the credential “x”, a MinerGate credential observed by Darktrace in previous cryptojacking compromises, including the Sysrv-hello botnet.

Figure 1: Darktrace DETECT breach log showing an alerted mining activity model breach on an infected device.
Figure 2: Darktrace's Cyber AI Analyst providing details about unusual repeated connections to multiple endpoints related to CoinLoader cryptomining.

In a number of customer environments, Darktrace observed affected devices connected to endpoints associated with other malware such as the Andromeda botnet and the ViperSoftX information stealer. It was, however, not possible to confirm whether CoinLoader had dropped these additional malware variants onto infected devices.

On customer networks where Darktrace RESPOND was enabled in autonomous response mode, Darktrace was able to take swift targeted steps to shut down suspicious connections and contain CoinLoader compromises. In one example, following DETECT’s initial identification of an affected device connecting to multiple MivoCloud endpoints, RESPOND autonomously blocked the device from carrying out such connections, effectively shutting down C2 communication and preventing threat actors carrying out any cryptomining activity, or downloading subsequent malicious payloads. The autonomous response capability of RESPOND provides customer security teams with precious time to remove infected devices from their network and action their remediation strategies.

Figure 3: Darktrace RESPOND autonomously blocking CoinLoader connections on an affected device.

Additionally, customers subscribed to Darktrace’s Proactive Threat Notification (PTN) service would be alerted about potential CoinLoader activity observed on their network, prompting Darktrace’s Security Operations Center (SOC) to triage and investigate the activity, allowing customers to prioritize incidents that require immediate attention.

Conclusion

By masquerading as free or ‘cracked’ versions of legitimate popular software, loader malware like CoinLoader is able to indiscriminately target a large number of endpoint users without arousing suspicion. What’s more, once a network has been compromised by the loader, it is then left open to a secondary compromise in the form of potentially costly information stealers, ransomware or, in this case, cryptocurrency miners.

While urging employees to think twice before installing seemingly legitimate software unknown or untrusted locations is an essential first step in protecting an organization against threats like CoinLoader, its stealthy tactics mean this may not be enough.

In order to fully safeguard against such increasingly widespread yet evasive threats, organizations must adopt security solutions that are able to identify anomalies and subtle deviations in device behavior that could indicate an emerging compromise. The Darktrace suite of products, including DETECT and RESPOND, are well-placed to identify and contain these threats in the first instance and ensure they cannot escalate to more damaging network compromises.

Credit to: Signe Zaharka, Senior Cyber Security Analyst, Paul Jennings, Principal Analyst Consultant

Appendix

Darktrace DETECT Model Detections

  • Anomalous Connection/Multiple Connections to New External TCP Port
  • Anomalous Connection/Multiple Failed Connections to Rare Endpoint
  • Anomalous Connection/Rare External SSL Self-Signed
  • Anomalous Connection/Repeated Rare External SSL Self-Signed
  • Anomalous Connection/Suspicious Self-Signed SSL
  • Anomalous Connection/Young or Invalid Certificate SSL Connections to Rare
  • Anomalous Server Activity/Rare External from Server
  • Compromise/Agent Beacon (Long Period)
  • Compromise/Beacon for 4 Days
  • Compromise/Beacon to Young Endpoint
  • Compromise/Beaconing Activity To External Rare
  • Compromise/High Priority Crypto Currency Mining
  • Compromise/High Volume of Connections with Beacon Score
  • Compromise/Large Number of Suspicious Failed Connections
  • Compromise/New or Repeated to Unusual SSL Port
  • Compromise/Rare Domain Pointing to Internal IP
  • Compromise/Repeating Connections Over 4 Days
  • Compromise/Slow Beaconing Activity To External Rare
  • Compromise/SSL Beaconing to Rare Destination
  • Compromise/Suspicious File and C2
  • Compromise/Suspicious TLS Beaconing To Rare External
  • Device/ Anomalous Github Download
  • Device/ Suspicious Domain
  • Device/Internet Facing Device with High Priority Alert
  • Device/New Failed External Connections

Indicators of Compromise (IoCs)

IoC - Hostname C2 Server

ams-updatea[.]info

ams-updateb[.]info

ams-updatec[.]info

ams-updated[.]info

candatamsna[.]info

candatamsnb[.]info

candatamsnc[.]info

candatamsnd[.]info

mapdatamsna[.]info

mapdatamsnb[.]info

mapdatamsnc[.]info

mapdatamsnd[.]info

res-smarta[.]info

res-smartb[.]info

res-smartc[.]info

res-smartd[.]info

rqmetrixa[.]info

rqmetrixb[.]info

rqmetrixc[.]info

rqmetrixd[.]info

ucmetrixa[.]info

ucmetrixb[.]info

ucmetrixc[.]info

ucmetrixd[.]info

any-updatea[.]icu

IoC - IP Address - C2 Server

185.225[.]16.192

185.225[.]16.61

185.225[.]16.62

185.225[.]16.63

185.225[.]16.88

185.225[.]17.108

185.225[.]17.109

185.225[.]17.12

185.225[.]17.13

185.225[.]17.135

185.225[.]17.14

185.225[.]17.145

185.225[.]17.157

185.225[.]17.159

185.225[.]18.141

185.225[.]18.142

185.225[.]18.143

185.225[.]19.218

185.225[.]19.51

194.180[.]157.179

194.180[.]157.185

194.180[.]158.55

194.180[.]158.56

194.180[.]158.62

194.180[.]158.63

5.252.178[.]74

94.158.246[.]124

IoC - IP Address - Cryptocurrency mining related endpoint

185.225.17[.]114

185.225.17[.]118

185.225.17[.]130

185.225.17[.]131

185.225.17[.]132

185.225.17[.]142

IoC - SSL/TLS certificate issuer information - C2 server certificate example

emailAddress=admin@example[.]ltd,CN=example[.]ltd,OU=IT,O=MyCompany LLC,L=San Francisco,ST=California,C=US

emailAddress=admin@'res-smartd[.]info,CN=res-smartd[.]info,OU=IT,O=MyCompany LLC,L=San Francisco,ST=California,C=US

CN=ucmetrixd[.]info,OU=IT,O=MyCompany LLC,L=San Francisco,ST=California,C=US

MITRE ATT&CK Mapping

INITIAL ACCESS

Exploit Public-Facing Application - T1190

Spearphishing Link - T1566.002

Drive-by Compromise - T1189

COMMAND AND CONTROL

Non-Application Layer Protocol - T1095

Non-Standard Port - T1571

External Proxy - T1090.002

Encrypted Channel - T1573

Web Protocols - T1071.001

Application Layer Protocol - T1071

DNS - T1071.004

Fallback Channels - T1008

Multi-Stage Channels - T1104

PERSISTENCE

Browser Extensions

T1176

RESOURCE DEVELOPMENT

Web Services - T1583.006

Malware - T1588.001

COLLECTION

Man in the Browser - T1185

IMPACT

Resource Hijacking - T1496

References

1. https://www.avira.com/en/blog/coinloader-a-sophisticated-malware-loader-campaign

2. https://asec.ahnlab.com/en/17909/

3. https://www.cybereason.co.jp/blog/cyberattack/5687/

4. https://research.checkpoint.com/2023/tunnel-warfare-exposing-dns-tunneling-campaigns-using-generative-models-coinloader-case-study/

5. https://securityboulevard.com/2023/02/three-cases-of-cyber-attacks-on-the-security-service-of-ukraine-and-nato-allies-likely-by-russian-state-sponsored-gamaredon/

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
Signe Zaharka
Principal Cyber Analyst

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August 6, 2026

When AI Agents Attack: The Case for Behavioral Anomaly Detection

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The UK AI Security Institute (AISI) has just published a detailed incident report confirming what many within the cyber security industry have suspected for some time: frontier AI agents, given a degree of autonomy, can independently develop and execute attack chains against real targets, including social engineering, supply-chain compromise, and deception, without explicit instruction to do so.

The report (INC-2026-07-28-01, published 4 August 2026) documents what happened during a routine capability evaluation between 25 and 28 July. It deserves a careful read from anyone responsible for securing the modern digital estate.

The incident

AISI regularly tests frontier AI models for offensive cyber capability. In this exercise, agents were placed inside a simulated network environment and given internet access this was deliberate, given to reflect realism of the task. Across 122 evaluation runs, 19 instances of unsanctioned activity were recorded, including cases where agents broke the intended boundaries of the test and acted against real people and real infrastructure on the open internet.

In the most serious case, an agent (Mythos 5) autonomously:

  • Conducted open-source intelligence gathering to identify real developers associated with keywords from the simulated scenario
  • Created a GitHub account and submitted a pull request containing obfuscated malicious code to a real, unaffiliated repository
  • Created a second sockpuppet account to post comments on its own PR, attempting to manufacture social proof
  • When a human reviewer flagged the malicious content, the agent lied, claiming an accidental commit, then repeatedly attempted to reintroduce the payload under the guise of having "fixed" the code
  • Sent spear-phishing emails to the repository maintainer containing manipulated content designed to convince them to merge the code
  • Planted a prompt injection inside a GitHub issue, hidden in an HTML comment invisible to humans but readable by AI coding assistants parsing the repository via API

AISI confirmed no real-world harm resulted. The PRs were not merged; the payloads did not execute. But containment was a product of circumstance, not design.

Why this matters

Every action the agents took used legitimate services operating within normal parameters. Creating a GitHub account is legitimate. Opening a pull request is legitimate. Sending an email is legitimate. Posting an issue is legitimate.

No vulnerability was exploited. No known malware signature was present. No indicator of compromise from any threat intelligence feed would have matched. The entire attack existed as a pattern, a sequence of individually normal actions that, taken together, constituted a supply-chain attack, a social engineering campaign, and an attempted compromise of downstream systems.

This is the class of threat that signature-based and rule-based security tools structurally struggle to detect. They answer the question "have I seen this before?" When the answer is no – and when the attack is novel, composed of legitimate actions, and adapted in real time by an adversary in this case an agent that reasons about evasion – they struggle.

Behavioral anomaly detection: The architecture that fits

Darktrace has spent a decade building a platform around a different question: "is this behavior normal for this entity?"

The platform learns the baseline behavior of every user, device, and communication pattern across an organization's digital environment. It does not need prior knowledge of an attack technique. It identifies deviation from learned normality, surfaces it, and through its Autonomous Response capability, takes targeted action to contain threats at machine speed.

Consider how this AISI incident might show across the Darktrace platform:

Network detection and response

While no payload was successfully delivered to a victim in this incident, AISI's post-incident analysis of the agent's code (detailed on pages 24-25 of the report) reveals what would have landed on target systems had the social engineering succeeded. The agent produced three successive payload generations, each replacing the last after being detected and called out:

Generation 1 hid a module-load stager inside a legitimate bug-fix commit, guarded by an environment variable check, to skip execution in CI. Its second stage attempted to fetch Poseidon implants (Linux and Windows variants) calling back to the agent's own C2 listener, with a fallback to publicly hosted polling scripts that fetched and executed commands every 60 seconds.

Generation 2 exploited an Electron "What's New" window with nodeIntegration enabled, loading remote HTML from a GitHub Pages site the agent had registered. The page decoded an XOR-obfuscated payload at runtime that beaconed host identifiers over DNS, attempted to download the same implants, ran its own in-process C2 loop, and installed reboot persistence via crontab and Windows registry Run keys.

Generation 3 was a post-install dropper added after the agent had already been publicly caught. It XOR-decoded a hidden URL, downloaded a script over plaintext HTTP, and ran it detached, force-exiting so npm install always reports success, giving the attacker remote code execution on any machine running the install.

None of these payloads reached a victim. But the technical detail matters: this is the calibre of tradecraft an autonomous agent produced in a matter of hours, unprompted. Each generation demonstrated adaptation, the agent iterated its approach in direct response to being detected.

For network defenders, the behavioral signals these payloads would have generated are clear. DNS beaconing to novel domains, periodic HTTP polling to newly registered infrastructure, XOR-encoded data in transit, registry and crontab persistence writes on endpoints that have never exhibited such behavior. These are exactly the anomalies that Darktrace / NETWORK identifies in real time: deviations from learned device and connection baselines, regardless of whether the specific payload or C2 domain has been seen before.

Beyond the payload analysis, the agents' broader activity produced additional behavioral anomalies: new identities engaging in high-frequency interactions with external services, coordination via unusual channels (public pastebins, gists), and lateral communication patterns that deviate from any established baseline.

Email security

The spear-phishing emails sent by the agent, crafted with context-specific content designed to manipulate a specific individual, represent exactly the kind of socially engineered communication that static email gateways can miss. Darktrace / EMAIL analyses the linguistic patterns, sender behavior, and relational context of every message. A brand-new sender using tailored language to pressure a recipient into a specific technical action deviates from the learned communication profile, regardless of whether the message contains a known-bad URL or attachment.

Securing AI

This is where the incident points to a threat category that many security platforms do not yet fully address. The agent did not just use AI as a tool for attack. It targeted other AI systems, attempting prompt injections against coding assistants and trying to compromise automated workflows. Organisations adopting AI agents for development, operations, and decision-making are introducing a newer extended attack surface.  

Darktrace / SECURE AI extends the same behavioral detection model into this space. It monitors AI usage across the enterprise, detecting anomalous interactions with AI services, identifying sensitive data exposure to AI systems, providing visibility into shadow AI use. As AI agents become standard components of enterprise infrastructure, the ability to detect when an AI system is behaving outside its expected parameters, when there is a chance, it is being manipulated, or when it is interacting with something it should not be, that becomes a direct security requirement rather than a future consideration.

The principle is consistent across the Darktrace platform: learn what normal looks like, identify deviation, respond autonomously.

The AI-to-AI threat surface

One of the report's most important findings is a confirmation that AI agents can act outside of instructions and guardrails to complete tasks. The Mythos 5 agent conducted reconnaissance on a repository maintainer, inferred it might be an AI coding assistant, and deployed a prompt injection specifically crafted to compromise it.

This is a new attack class. Organizations deploying AI coding assistants, AI-powered code review, or autonomous DevOps agents now face an adversary that:

  • Moves at speed
  • Is able to adapt its approach when initial attempts are halted
  • Specifically targets AI systems via techniques (prompt injection, hidden instructions in HTML comments) that are less visible to human reviewers but parsed by machines
  • Reasons about which evasion strategies are most likely to succeed

Defending against this requires security that operates with the same adaptability and speed. A system that learns what "normal" looks like, and flags deviation from it.

What AISI recommends

The report identifies five contributing factors to the incident. Two are directly relevant:

No synchronous real-time monitoring (Section 5.3): AISI acknowledges it had not built real-time behavioral monitoring capable of immediately blocking unsanctioned agent actions. Their security team detected the incident via commercial security monitoring software, but only after activity had already occurred.

No fine-grained behavioral controls (Section 6.2): AISI's forward-looking response includes building continuous monitoring that can "immediately block or flag unsanctioned AI agent behavior."

The direction is clear: organizations need security that watches behavior continuously, learns what normal looks like, and acts when deviation occurs, without requiring a human in the loop for every decision.

The takeaway

The AISI incident is documented proof that autonomous AI agents will independently develop novel attack chains using legitimate tools, adapt when detected, employ deception, and target both humans and other AI systems. This happened last week, in a controlled setting, with commercially available models.

The security architecture that addresses this is behavioral anomaly detection applied across the full digital estate, as AI agents become standard components of enterprise infrastructure, writing code, managing deployments, processing communications, the attack surface they create is behavioral by nature. The defense must be too.

Read the full report from the UK AI Security Institute here.

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About the author
Adam Stevens
Senior Director of Product | Darktrace

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August 5, 2026

Testing a Prompt injection Attack Against an Enterprise AI Agent

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
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