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December 7, 2023

How Darktrace Triumphed Over MyKings Botnet

Darktrace has provided full visibility over the MyKings botnet kill chain from the beginning of its infections to the eventual cryptocurrency mining activity.
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
Oluwatosin Aturaka
Analyst Team Lead, Cambridge
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07
Dec 2023

Botnets: A persistent cyber threat

Since their appearance in the wild over three decades ago, botnets have consistently been the attack vector of choice for many threat actors. The most prevalent of these attack vectors are distributed denial of service (DDoS) and phishing campaigns. Their persistent nature means that even if a compromised device in identified, attackers can continue to operate by using the additional compromised devices they will likely have on the target network. Similarly, command and control (C2) infrastructure can easily be restructured between infected systems, making it increasingly difficult to remove the infection.  

MyKings Botnet

One of the most prevalent and sophisticated examples in recent years is the MyKings botnet, also known as Smominru or DarkCloud. Darktrace has observed numerous cases of MyKings botnet compromises across multiple customer environments in several different industries as far back as August 2022. The diverse tactics, techniques, and procedures (TTPs) and sophisticated kill chains employed by MyKings botnet may prove a challenge to traditional rule and signature-based detections.

However, Darktrace’s anomaly-centric approach enabled it to successfully detect a wide-range of indicators of compromise (IoCs) related to the MyKings botnet and bring immediate awareness to customer security teams, as it demonstrated on the network of multiple customers between March and August 2023.

Background on MyKings Botnet

MyKings has been active and spreading steadily since 2016 resulting in over 520,000 infections worldwide.[1] Although verified attribution of the botnet remains elusive, the variety of targets and prevalence of crypto-mining software on affected devices suggests the threat group behind the malware is financially motivated. The operators behind MyKings appear to be highly opportunistic, with attacks lacking an obvious specific target industry. Across Darktrace’s customer base, the organizations affected were representative of multiple industries such as entertainment, mining, education, information technology, health, and transportation.

Given its longevity, the MyKings botnet has unsurprisingly evolved since its first appearance years ago. Initial analyses of the botnet showed that the primary crypto-related activity on infected devices was the installation of Monero-mining software. However, in 2019 researchers discovered a new module within the MyKings malware that enabled clipboard-jacking, whereby the malware replaces a user's copied cryptowallet address with the operator's own wallet address in order to siphon funds.[2]

Similar to other botnets such as the Outlaw crypto-miner, the MyKings botnet can also kill running processes of unrelated malware on the compromised hosts that may have resulted from prior infection.[3] MyKings has also developed a comprehensive set of persistence techniques, including: the deployment of bootkits, initiating the botnet immediately after a system reboot, configuring Registry run keys, and generating multiple Scheduled Tasks and WMI listeners.[4] MyKings have also been observed rotating tools and payloads over time to propagate the botnet. For example, some operators have been observed utilizing PCShare, an open-source remote access trojan (RAT) customized to conduct C2 services, execute commands, and download mining software[5].

Darktrace Coverage

Across observed customer networks between March and August 2023, Darktrace identified the MyKings botnet primarily targeting Windows-based servers that supports services like MySQL, MS-SQL, Telnet, SSH, IPC, WMI, and Remote Desktop (RDP).  In the initial phase of the attack, the botnet would initiate a variety of attacks against a target including brute-forcing and exploitation of unpatched vulnerabilities on exposed servers. The botnet delivers a variety of payloads to the compromised systems including worm downloaders, trojans, executable files and scripts.

This pattern of activity was detected across the network of one particular Darktrace customer in the education sector in early March 2023. Unfortunately, this customer did not have Darktrace RESPOND™ deployed on their network at the time of the attack, meaning the MyKings botnet was able to move through the cyber kill chain ultimately achieving its goal, which in this case was mining cryptocurrency.

Initial Access

On March 6, Darktrace observed an internet-facing SQL server receiving an unusually large number of incoming MySQL connections from the rare external endpoint 171.91.76[.]31 via port 1433. While it is not possible to confirm whether these suspicious connections represented the exact starting point of the infection, such a sudden influx of SQL connection from a rare external endpoint could be indicative of a malicious attempt to exploit vulnerabilities in the server's SQL database or perform password brute-forcing to gain unauthorized access. Given that MyKings typically spreads primarily through such targeting of internet-exposed devices, the pattern of activity is consistent with potential initial access by MyKings.[6]

Initial Command and Control

The device then proceeded to initiate a series of repeated HTTP connections between March 6 and March 10, to the domain www[.]back0314[.]ru (107.148.239[.]111). These connections included HTTP GET requests featuring URIs such as ‘/back.txt',  suggesting potential beaconing and C2 communication. The device continued this connectivity to the external host over the course of four days, primarily utilizing destination ports 80, and 6666. While port 80 is commonly utilized for HTTP connections, port 6666 is a non-standard port for the protocol. Such connectivity over non-standard ports can indicate potential detection evasion and obfuscation tactics by the threat actors.  During this time, the device also initiated repeated connections to additional malicious external endpoints with seemingly algorithmically generated hostnames such as pc.pc0416[.]xyz.

Darktrace UI image
Figure 1: Model breach showing details of the malicious domain generation algorithm (DGA) connections.

Tool Transfer

While this beaconing activity was taking place, the affected device also began to receive potential payloads from unusual external endpoints. On April 29, the device made an HTTP GET request for “/power.txt” to the endpoint 192.236.160[.]237, which was later discovered to have multiple open-source intelligence (OSINT) links to malware. Power.txt is a shellcode written in PowerShell which is downloaded and executed with the purpose of disabling Windows Defenders related functions.[7] After the initial script was downloaded (and likely executed), Darktrace went on to detect the device making a series of additional GET requests for several varying compressed and executable files. For example, the device made HTTP requests for '/pld/cmd.txt' to the external endpoint 104.233.224[.]173. In response the external server provided numerous files, including ‘u.exe’, and ‘upsup4.exe’ for download, both of which share file names with previously identified MyKings payloads.

MyKings deploys a diverse array of payloads to expand the botnet and secure a firm position within a compromised system. This multi-faceted approach may render conventional security measures less effective due to the intricacies of and variety of payloads involved in compromises. Darktrace, however, does not rely on static or outdated lists of IoCs in order to detect malicious activity. Instead, DETECT’s Self-Learning AI allows it to identify emerging compromise activity by recognizing the subtle deviations in an affected device’s behavior that could indicate it has fallen into the hands of malicious actors.

Figure 2: External site summary of the endpoint 103.145.106[.]242 showing the rarity of connectivity to the external host.

Achieving Objectives – Crypto-Mining

Several weeks after the initial payloads were delivered and beaconing commenced, Darktrace finally detected the initiation of crypto-mining operations. On May 27, the originally compromised server connected to the rare domain other.xmrpool[.]ru over port 1081. As seen in the domain name, this endpoint appears to be affiliated with pool mining activity and the domain has various OSINT affiliations with the cryptocurrency Monero coin. During this connection, the host was observed passing Monero credentials, activity which parallels similar mining operations observed on other customer networks that had been compromised by the MyKings botnet.

Although mining activity may not pose an immediate or urgent concern for security unauthorized cryptomining on devices can result in detrimental consequences, such as compromised hardware integrity, elevated energy costs, and reduced productivity, and even potential involvement in money laundering.

Figure 3: Event breach log showing details of the connection to the other.xmrpool[.]ru endpoint associated with cryptocurrency mining activity.

Conclusion

Detecting future iterations of the MyKings botnet will likely demand a shift away from an overreliance on traditional rules and signatures and lists of “known bads”, instead requiring organizations to employ AI-driven technology that can identify suspicious activity that represents a deviation from previously established patterns of life.

Despite the diverse range of payloads, malicious endpoints, and intricate activities that constitute a typical MyKing botnet compromise, Darktrace was able successfully detect multiple critical phases within the MyKings kill chain. Given the evolving nature of the MyKings botnet, it is highly probable the botnet will continue to expand and adapt, leveraging new tactics and technologies. By adopting Darktrace’s product of suites, including Darktrace DETECT, organizations are well-positioned to identify these evolving threats as soon as they emerge and, when coupled with the autonomous response technology of Darktrace RESPOND, threats like the MyKings botnet can be stopped in their tracks before they can achieve their ultimate goals.

Credit to: Oluwatosin Aturaka, Analyst Team Lead, Cambridge, Adam Potter, Cyber Analyst

Appendix

IoC Table

IoC - Type - Description + Confidence

162.216.150[.]108- IP - C2 Infrastructure

103.145.106[.]242 - IP - C2 Infrastructure

137.175.56[.]104 - IP - C2 Infrastructure

138.197.152[.]201 - IP - C2 Infrastructure

139.59.74[.]135 - IP - C2 Infrastructure

pc.pc0416[.]xyz - Domain - C2 Infrastructure (DGA)

other.xmrpool[.]ru - Domain - Cryptomining Endpoint

xmrpool[.]ru - Domain - Cryptomining Endpoint

103.145.106[.]55 - IP - Cryptomining Endpoint

ntuser[.]rar - Zipped File - Payload

/xmr1025[.]rar - Zipped File - Payload

/20201117[.]rar - Zipped File - Payload

wmi[.]txt - File - Payload

u[.]exe - Executable File - Payload

back[.]txt - File - Payload

upsupx2[.]exe - Executable File - Payload

cmd[.]txt - File - Payload

power[.]txt - File - Payload

ups[.]html - File - Payload

xmr1025.rar - Zipped File - Payload

171.91.76[.]31- IP - Possible Initial Compromise Endpoint

www[.]back0314[.]ru - Domain - Probable C2 Infrastructure

107.148.239[.]111 - IP - Probable C2 Infrastructure

194.67.71[.]99 - IP- Probable C2 Infrastructure

Darktrace DETECT Model Breaches

  • Device / Initial Breach Chain Compromise
  • Anomalous File / Masqueraded File Transfer (x37)
  • Compromise / Large DNS Volume for Suspicious Domain
  • Compromise / Fast Beaconing to DGA
  • Device / Large Number of Model Breaches
  • Anomalous File / Multiple EXE from Rare External Locations (x30)
  • Compromise / Beacon for 4 Days (x2)
  • Anomalous Server Activity / New User Agent from Internet Facing System
  • Anomalous Connection / New User Agent to IP Without Hostname
  • Anomalous Server Activity / New Internet Facing System
  • Anomalous File / EXE from Rare External Location (x37)
  • Device / Large Number of Connections to New Endpoints
  • Anomalous Server Activity / Server Activity on New Non-Standard Port (x3)
  • Device / Threat Indicator (x3)
  • Unusual Activity / Unusual External Activity
  • Compromise / Crypto Currency Mining Activity (x37)
  • Compliance / Internet Facing SQL Server
  • Device / Anomalous Scripts Download Followed By Additional Packages
  • Device / New User Agent

MITRE ATT&CK Mapping

ATT&CK Technique - Technique ID

Reconnaissance – T1595.002 Vulnerability Scanning

Resource Development – T1608 Stage Capabilities

Resource Development – T1588.001 Malware

Initial Access – T1190 Exploit Public-Facing Application

Command and Control – T15568.002 Domain Generated Algorithms

Command and Control – T1571 Non-Standard Port

Execution – T1047 Windows Management Instrumentation

Execution – T1059.001 Command and Scripting Interpreter

Persistence – T1542.003 Pre-OS Boot

Impact – T1496 Resource Hijacking

References

[1] https://www.binarydefense.com/resources/threat-watch/mykings-botnet-is-growing-and-remains-under-the-radar/

[2] https://therecord.media/a-malware-botnet-has-made-more-than-24-7-million-since-2019

[3] https://www.darktrace.com/blog/outlaw-returns-uncovering-returning-features-and-new-tactics

[4] https://www.sophos.com/en-us/medialibrary/pdfs/technical-papers/sophoslabs-uncut-mykings-report.pdf

[5] https://www.antiy.com/response/20190822.html

[6] https://ethicaldebuggers.com/mykings-botnet/

[7] https://ethicaldebuggers.com/mykings-botnet/

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
Oluwatosin Aturaka
Analyst Team Lead, Cambridge

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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

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Key takeaways

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

How behavioral detection helps stop prompt injection attacks

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

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

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

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

How do prompt injection attacks work?

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

Prompt injection attack example

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

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

How we tested prompt injection attacks on an enterprise agent

Summary:

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

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

Figure 1
Figure 2

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

How Darktrace detected a prompt injection attack

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

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

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

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

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

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

Why behavioral security makes a difference detecting prompt injection attacks

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

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

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

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

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

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

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

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

Why enterprise AI security requires more than guardrails

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

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

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

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

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

That's where behavioral detection comes in.

How Darktrace detects prompt injection attacks in emails

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

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

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

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

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

How to secure enterprise AI operations from prompt injection attacks

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

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

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

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

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

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

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

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About the author
Carlo Loregian
Solutions Engineer
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