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July 27, 2023

Revealing Outlaw's Returning Features & New Tactics

Darktrace's investigation of the latest Outlaw crypto-mining operation, covering the resurgence of old tactics along with the emergence of new ones.
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
Adam Potter
Senior Cyber Analyst
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27
Jul 2023

What is Outlaw Cryptocurrency Mining Operation?

The cybersecurity community has been aware of the threat of Outlaw cryptocurrency mining operation, and its affiliated activities since as early as 2018. Despite its prominence, Outlaw remains largely elusive to researchers and analysts due to its ability to adapt its tactics, procedures, and payloads.

Outlaw gained notoriety in 2018 as security researchers began observing the creation of affiliated botnets.[1][2]  Researchers gave Outlaw  its name based on the English translation of the “Haiduc” tool observed during their initial activity on compromised devices.[3],[4] By 2019, much of the initial Outlaw activity  focused on the targeting of Internet of Things (IoT) devices and other internet facing servers, reportedly focusing operations in China and on Chinese devices.[5],[6]  From the outset, mining operations featured as a core element of botnets created by the group.[7] This initial focus may have been a sign of caution by threat actors or a preliminary means of testing procedures and operation efficacy. Regardless, Outlaw actors inevitably expanded scope, targeting larger organizations and a wider range of internet facing devices across geographic scope.

Following a short period of inactivity, security researchers began to observe new Outlaw activity, showcasing additional capabilities such as the ability to kill existing crypto-mining processes on devices, thereby reclaiming devices already compromised by crypto-jacking. [8],[9]

Latest News on Outlaw

Although the more recently observed incidents of Outlaw did demonstrate some new tactics, many of its procedures remained the same, including its unique bundling of payloads that combine crypto-mining and botnet capabilities. [10] In conjunction, the continued use of mining-specific payloads and growth of affiliated botnets has bolstered the belief that Outlaw actors historically prioritizes financial gain, in lieu of overt political objectives.

Given the tendency for malicious actors to share tools and capabilities, true attribution of threat or threat group is extremely difficult in the wild. As such, a genuine survey of activity from the group across a customer base has not always been possible. Therefore, we will present an updated look into more recent activity associated with Outlaw detected across the Darktrace customer base.  

Darktrace vs Outlaw

Since late 2022, Darktrace has observed a rise in probable cyber incidents involving indicators of compromise (IoCs) associated with Outlaw. Given its continued prevalence and relative dearth of information, it is essential to take a renewed look at the latest campaign activity associated with threats like Outlaw to avoid making erroneous assumptions and to ensure the threat posed is correctly characterized.

While being aware of previous IoCs and tactics known to be employed in previous campaigns will go some way to protecting against future Outlaw attacks, it is paramount for organizations to arm themselves with an autonomous intelligent decision maker that can identify malicious activity, based on recognizing deviations from expected patterns of behavior, and take preventative action to effectively defend against such a versatile threat.

Darktrace’s anomaly-based approach to threat detection means it is uniquely positioned to detect novel campaign activity by recognizing subtle deviations in affected devices’ behavior that would have gone unnoticed by traditional security tools relying on rules, signatures and known IoCs.

Outlaw Attack Overview & Darktrace Coverage

From late 2022 through early 2023, Darktrace identified multiple cyber events involving IP addresses, domains, and payloads associated with Outlaw on customer networks. In this recent re-emergence of campaign activity, Darktrace identified numerous attack vectors and IoCs that had previously been associated with Outlaw, however it also observed significant deviations from previous campaigns.

Returning Features

As outlined in a previous blog, past iterations of Outlaw compromises include four identified, distinct phases:

1. Targeting of internet facing devices via SSH brute-forcing

2. Initiation of crypto-mining operations

3. Download of shell script and/or botnet malware payloads

4. Outgoing external SSH scanning to propagate the botnet

Nearly all affected devices analyzed by Darktrace were tagged as internet facing, as identified in previous campaigns, supporting the notion that Outlaw continues to focus on easily exposed devices. In addition to this, Darktrace observed three other core returning features from previous Outlaw campaigns in affected devices between late 2022 and early 2023:

1. Gzip and/or Script Download

2. Beaconing Activity (Command and Control)

3. Crypto-mining

Gzip and/or Script Download

Darktrace observed numerous devices downloading the Dota malware, a strain that is previously known to have been associated with the Outlaw botnet, as either a gzip file or a shell script from rare external hosts.

In some examples, IP addresses that provided the payload were flagged by open-source intelligence (OSINT) sources as having engaged in widespread SSH brute-forcing activities. While the timing of the payload transfer to the device was not consistent, download of gzip files featured prominently during directly observed or potentially affiliated activity. Moreover, Darktrace detected multiple devices performing HTTP requests for shell scripts (.sh) according to detected connection URIs. Darktrace DETECT was able to identify these anomalous connections due to the rarity of the endpoint, payloads, and connectivity for the devices.

Figure 1: Darktrace Cyber AI Analyst technical details summary from an incident during the analysis timeframe that highlights a breach device retrieving the anomalous shell scripts using wget.

Beaconing Activity – Command and Control (C2) Endpoint

Across all Outlaw activity identified by Darktrace, devices engaged in some form of beaconing behavior, rather than one-off connections to IPs associated with Outlaw. While the use of application protocol was not uniform, repeated connectivity to rare external IP addresses related to Outlaw occurred across many analyzed incidents. Darktrace’s Self-Learning AI understood that this beaconing activity represented devices deviating from their expected patterns of life and was able to bring it to the immediate attention of customer security teams.

Figure 2: Model breach log details showing sustained, repeated connectivity to Outlaw affiliated endpoint over port 443, indicating potential C2 activity.

Crypto-mining

In almost every incident of Outlaw identified across the fleet, Darktrace detected some form of cryptocurrency mining activity. Devices affected by Outlaw were consistently observed making anomalous connections to external endpoints associated with crypto-mining operations. Furthermore, the Minergate protocol appeared consistently across hosts; even when devices did not make direct crypto-mining commands, such hosts attempted connections to external entities that were known to support crypto-mining operations.

Figure 3: Advanced Search results showing a sudden spike in mining activity from a device observed connecting to Outlaw-affiliated IP addresses. Such crypto-mining activity was observed consistently across analyzed incidents.

Is Outlaw Using New Tactics?

While in the past, Outlaw activity was identified through a systematic kill chain, recent investigations conducted by Darktrace show significant deviations from this.

For instance, affected devices do not necessarily follow the previously outlined kill chain directly as they did previously. Instead, Darktrace observed affected devices exhibiting these phases in differing orders, repeating steps, or missing out attack phases entirely.

It is essential to study such variation in the kill chain to learn more about the threat of Outlaw and how threat actors are continuing to use it is varying ways. These discrepancies in kill chain elements are likely impacted by visibility into the networks and devices of Darktrace customers, with some relevant activity falling outside of Darktrace’s purview. This is particularly true for internet-exposed devices and hosts that repeatedly performed the same anomalous activity (such as making Minergate requests). Moreover, some devices involved in Outlaw activity may have already been compromised prior to Darktrace’s visibility into the network. As such, these conclusions must be evaluated with a degree of uncertainty.

SSH Activity

Although external SSH connectivity was apparent in some of the incidents detected by Darktrace, it was not directly related to brute-forcing activity. Affected devices did receive anomalous incoming SSH connections, however, wide ranging SSH failed connectivity following the initiation of mining operations by compromised devices was not readily apparent across analyzed compromises. Connections over port 22 were more frequently associated with beaconing and/or C2 activity to endpoints associated with Outlaw, than with potential brute-forcing. As such, Darktrace could not, with high confidence correlate such SSH activity to brute-forcing. This could suggest that threat actors are now portioning or rotation of botnet devices for different operations, for example dividing between botnet expansion and mining operations.

Command line tools

In cases of Outlaw investigated by Darktrace, there was also a degree of variability involving the tools used to retrieve payloads. On the networks of customers affected by Outlaw, Darktrace DETECT identified the use of user agents and command line tools that it considered to be out of character for the network and its devices.

When retrieving the Dota malware payload or shell script data, compromised devices frequently relied on numerous versions of wget and curl user agents. Although the use of such tools as a tactic cannot be definitively linked to the crypto-mining campaign, the employment of varying and/or outdated native command line tools attests to the procedural flexibility of Outlaw campaigns, and its potential for continued evolution.

Figure 4: Breach log data showing use of curl and wget tools to connect to IP addresses associated with Outlaw.

Outlaw in 2023

Given Outlaw’s widespread notoriety and its continued activities, it is likely to remain a prominent threat to organizations and security teams across the threat landscape in 2023 and beyond.

As Darktrace has observed within its customer base from late 2022 through early 2023, activity linked with the Outlaw cryptocurrency mining campaign continues to transpire, offering security teams and research a renewed look at how it has evolved and adapted over the years. While many of its features and tactics appear to have remained consistent, Darktrace has identified numerous signs of Outlaw deviating from its previously known activities.

While relying on previously established IoCs and known tactics from previous campaigns will go some way to protecting an organization’s network from Outlaw compromises, there is a greater need than ever to go further than this. Rather than depending on a list of known-bads or traditional signatures and rules, Darktrace’s anomaly-based approach to threat detection and unparallel autonomous response capabilities mean it is uniquely positioned to DETECT and RESPOND to Outlaw activity, regardless of how it evolves in the future.

Credit to: Adam Potter, Cyber Analyst, Nahisha Nobregas, SOC Analyst, and Ryan Traill, Threat Content Lead

Relevant DETECT Model Breaches:

Compliance / Incoming SSH  

Device / New User Agent and New IP

Device / New User Agent  

Anomalous Connection / New User Agent to IP Without Hostname  

Compromise / Crypto Currency Mining Activity  

Anomalous File / Internet Facing System File Download  

Anomalous Server Activity / New User Agent from Internet Facing System  

Anomalous File / Zip or Gzip from Rare External Location  

Anomalous File / Script from Rare External Location  

Anomalous Connection / Multiple Failed Connections to Rare Endpoint  

Compromise / Large Number of Suspicious Failed Connections  

Anomalous Server Activity / Outgoing from Server  

Compromise / Sustained TCP Beaconing Activity To Rare Endpoint

Indicators of Compromise

Indicator - Type - Description

/dota3.tar.gz​

File  URI​

Outlaw  payload​

/tddwrt7s.sh​

File  URI​

Outlaw  payload​

73e5dbafa25946ed636e68d1733281e63332441d​

SHA1  Hash​

Outlaw  payload​

debian-package[.]center​

Hostname​

Outlaw  C2 endpoint​

161.35.236[.]24​

IP  address​

Outlaw  C2 endpoint​

138.68.115[.]96​

IP  address​

Outlaw C2  endpoint​

67.205.134[.]224​

IP  address​

Outlaw C2  endpoint​

138.197.212[.]204​

IP  address​

Outlaw C2  endpoint​

45.9.148[.]59 ​

IP  address​

Possible  Outlaw C2 endpoint​

45.9.148[.]117​

IP  address​

Outlaw C2  endpoint​

45.9.148[.]125​

IP  address​

Outlaw C2  endpoint​

45.9.148[.]129​

IP  address​

Outlaw C2  endpoint​

45.9.148[.]99 ​

IP  address​

Outlaw C2  endpoint​

45.9.148[.]234​

IP  address​

Possible  Outlaw C2 endpoint​

45.9.148[.]236​

IP  address​

Possible  Outlaw C2 endpoint​

159.203.102[.]122​

IP  address​

Outlaw C2  endpoint​

159.203.85[.]196​

IP  address​

Outlaw C2  endpoint​

159.223.235[.]198​

IP  address​

Outlaw C2  endpoint​

MITRE ATT&CK Mapping

Tactic -Technique

Initial Access -T1190  Exploit - Public Facing Application

Command and Control - T1071 - Application - Layer Protocol

T1071.001 - Application Layer Protocol: Web Protocols

Impact - T1496 Resource Hijacking

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
Adam Potter
Senior 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
Your data. Our AI.
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