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November 27, 2023

Detecting PurpleFox Rootkit with Darktrace AI

The PurpleFox rootkit poses significant risks. Discover how Darktrace leveraged advanced techniques to combat this persistent cyber threat.
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
Piramol Krishnan
Cyber Security Analyst
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27
Nov 2023

Versatile Malware: PurpleFox

As organizations and security teams across the world move to bolster their digital defenses against cyber threats, threats actors, in turn, are forced to adopt more sophisticated tactics, techniques and procedures (TTPs) to circumvent them. Rather than being static and predictable, malware strains are becoming increasingly versatile and therefore elusive to traditional security tools.

One such example is PurpleFox. First observed in 2018, PurpleFox is a combined fileless rootkit and backdoor trojan known to target Windows machines. PurpleFox is known for consistently adapting its functionalities over time, utilizing different infection vectors including known vulnerabilities (CVEs), fake Telegram installers, and phishing. It is also leveraged by other campaigns to deliver ransomware tools, spyware, and cryptocurrency mining malware. It is also widely known for using Microsoft Software Installer (MSI) files masquerading as other file types.

The Evolution of PurpleFox

The Original Strain

First reported in March 2018, PurpleFox was identified to be a trojan that drops itself onto Windows machines using an MSI installation package that alters registry values to replace a legitimate Windows system file [1]. The initial stage of infection relied on the third-party toolkit RIG Exploit Kit (EK). RIG EK is hosted on compromised or malicious websites and is dropped onto the unsuspecting system when they visit browse that site. The built-in Windows installer (MSIEXEC) is leveraged to run the installation package retrieved from the website. This, in turn, drops two files into the Windows directory – namely a malicious dynamic-link library (DLL) that acts as a loader, and the payload of the malware. After infection, PurpleFox is often used to retrieve and deploy other types of malware.  

Subsequent Variants

Since its initial discovery, PurpleFox has also been observed leveraging PowerShell to enable fileless infection and additional privilege escalation vulnerabilities to increase the likelihood of successful infection [2]. The PowerShell script had also been reported to be masquerading as a .jpg image file. PowerSploit modules are utilized to gain elevated privileges if the current user lacks administrator privileges. Once obtained, the script proceeds to retrieve and execute a malicious MSI package, also masquerading as an image file. As of 2020, PurpleFox no longer relied on the RIG EK for its delivery phase, instead spreading via the exploitation of the SMB protocol [3]. The malware would leverage the compromised systems as hosts for the PurpleFox payloads to facilitate its spread to other systems. This mode of infection can occur without any user action, akin to a worm.

The current iteration of PurpleFox reportedly uses brute-forcing of vulnerable services, such as SMB, to facilitate its spread over the network and escalate privileges. By scanning internet-facing Windows computers, PurpleFox exploits weak passwords for Windows user accounts through SMB, including administrative credentials to facilitate further privilege escalation.

Darktrace detection of PurpleFox

In July 2023, Darktrace observed an example of a PurpleFox infection on the network of a customer in the healthcare sector. This observation was a slightly different method of downloading the PurpleFox payload. An affected device was observed initiating a series of service control requests using DCE-RPC, instructing the device to make connections to a host of servers to download a malicious .PNG file, later confirmed to be the PurpleFox rootkit. The device was then observed carrying out worm-like activity to other external internet-facing servers, as well as scanning related subnets.

Darktrace DETECT™ was able to successfully identify and track this compromise across the cyber kill chain and ensure the customer was able to take swift remedial action to prevent the attack from escalating further.

While the customer in question did have Darktrace RESPOND™, it was configured in human confirmation mode, meaning any mitigative actions had to be manually applied by the customer’s security team. If RESPOND had been enabled in autonomous response mode at the time of the attack, it would have been able to take swift action against the compromise to contain it at the earliest instance.

Attack Overview

Figure 1: Timeline of PurpleFox malware kill chain.

Initial Scanning over SMB

On July 14, 2023, Darktrace detected the affected device scanning other internal devices on the customer’s network via port 445. The numerous connections were consistent with the aforementioned worm-like activity that has been reported from PurpleFox behavior as it appears to be targeting SMB services looking for open or vulnerable channels to exploit.

This initial scanning activity was detected by Darktrace DETECT, specifically through the model breach ‘Device / Suspicious SMB Scanning Activity’. Darktrace’s Cyber AI Analyst™ then launched an autonomous investigation into these internal connections and tied them into one larger-scale network reconnaissance incident, rather than a series of isolated connections.

Figure 2: Cyber AI Analyst technical details summarizing the initial scanning activity seen with the internal network scan over port 445.

As Darktrace RESPOND was configured in human confirmation mode, it was unable to autonomously block these internal connections. However, it did suggest blocking connections on port 445, which could have been manually applied by the customer’s security team.

Figure 3: The affected device’s Model Breach Event Log showing the initial scanning activity observed by Darktrace DETECT and the corresponding suggested RESPOND action.

Privilege Escalation

The device successfully logged in via NTLM with the credential, ‘administrator’. Darktrace recognized that the endpoint was external to the customer’s environment, indicating that the affected device was now being used to propagate the malware to other networks. Considering the lack of observed brute-force activity up to this point, the credentials for ‘administrator’ had likely been compromised prior to Darktrace’s deployment on the network, or outside of Darktrace’s purview via a phishing attack.

Exploitation

Darktrace then detected a series of service control requests over DCE-RPC using the credential ‘admin’ to make SVCCTL Create Service W Requests. A script was then observed where the controlled device is instructed to launch mshta.exe, a Windows-native binary designed to execute Microsoft HTML Application (HTA) files. This enables the execution of arbitrary script code, VBScript in this case.

Figure 4: PurpleFox remote service control activity captured by a Darktrace DETECT model breach.
Figure 5: The infected device’s Model Breach Event Log showing the anomalous service control activity being picked up by DETECT.

There are a few MSIEXEC flags to note:

  • /i : installs or configures a product
  • /Q : sets the user interface level. In this case, it is set to ‘No UI’, which is used for “quiet” execution, so no user interaction is required

Evidently, this was an attempt to evade detection by endpoint users as it is surreptitiously installed onto the system. This corresponds to the download of the rootkit that has previously been associated with PurpleFox. At this stage, the infected device continues to be leveraged as an attack device and scans SMB services over external endpoints. The device also appeared to attempt brute-forcing over NTLM using the same ‘administrator’ credential to these endpoints. This activity was identified by Darktrace DETECT which, if enabled in autonomous response mode would have instantly blocked similar outbound connections, thus preventing the spread of PurpleFox.

Figure 6: The infected device’s Model Breach Event Log showing the outbound activity corresponding to PurpleFox’s wormlike spread. This was caught by DETECT and the corresponding suggested RESPOND action.

Installation

On August 9, Darktrace observed the device making initial attempts to download a malicious .PNG file. This was a notable change in tactics from previously reported PurpleFox campaigns which had been observed utilizing .MOE files for their payloads [3]. The .MOE payloads are binary files that are more easily detected and blocked by traditional signatured-based security measures as they are not associated with known software. The ubiquity of .PNG files, especially on the web, make identifying and blacklisting the files significantly more difficult.

The first connection was made with the URI ‘/test.png’.  It was noted that the HTTP method here was HEAD, a method similar to GET requests except the server must not return a message-body in the response.

The metainformation contained in the HTTP headers in response to a HEAD request should be identical to the information sent in response to a GET request. This method is often used to test hypertext links for validity and recent modification. This is likely a way of checking if the server hosting the payload is still active. Avoiding connections that could possibly be detected by antivirus solutions can help keep this activity under-the-radar.

Figure 7: Packet Capture from an affected customer device showing the initial HTTP requests to the payload server.
Figure 8: Packet Capture showing the HTTP requests to download the payloads.

The server responds with a status code of 200 before the download begins. The HEAD request could be part of the attacker’s verification that the server is still running, and that the payload is available for download. The ‘/test.png’ HEAD request was sent twice, likely for double confirmation to begin the file transfer.

Figure 9: PCAP from the affected customer device showing the Windows Installer user-agent associated with the .PNG file download.

Subsequent analysis using a Packet Capture (PCAP) tool revealed that this connection used the Windows Installer user agent that has previously been associated with PurpleFox. The device then began to download a payload that was masquerading as a Microsoft Word document. The device was thus able to download the payload twice, from two separate endpoints.

By masquerading as a Microsoft Word file, the threat actor was likely attempting to evade the detection of the endpoint user and traditional security tools by passing off as an innocuous text document. Likewise, using a Windows Installer user agent would enable threat actors to bypass antivirus measures and disguise the malicious installation as legitimate download activity.  

Darktrace DETECT identified that these were masqueraded file downloads by correctly identifying the mismatch between the file extension and the true file type. Subsequently, AI Analyst was able to correctly identify the file type and deduced that this download was indicative of the device having been compromised.

In this case, the device attempted to download the payload from several different endpoints, many of which had low antivirus detection rates or open-source intelligence (OSINT) flags, highlighting the need to move beyond traditional signature-base detections.

Figure 10: Cyber AI Analyst technical details summarizing the downloads of the PurpleFox payload.
Figure 11 (a): The Model Breach generated by the masqueraded file transfer associated with the PurpleFox payload.
Figure 11 (b): The Model Breach generated by the masqueraded file transfer associated with the PurpleFox payload.

If Darktrace RESPOND was enabled in autonomous response mode at the time of the attack it would have acted by blocking connections to these suspicious endpoints, thus preventing the download of malicious files. However, as RESPOND was in human confirmation mode, RESPOND actions required manual application by the customer’s security team which unfortunately did not happen, as such the device was able to download the payloads.

Conclusion

The PurpleFox malware is a particularly dynamic strain known to continually evolve over time, utilizing a blend of old and new approaches to achieve its goals which is likely to muddy expectations on its behavior. By frequently employing new methods of attack, malicious actors are able to bypass traditional security tools that rely on signature-based detections and static lists of indicators of compromise (IoCs), necessitating a more sophisticated approach to threat detection.  

Darktrace DETECT’s Self-Learning AI enables it to confront adaptable and elusive threats like PurpleFox. By learning and understanding customer networks, it is able to discern normal network behavior and patterns of life, distinguishing expected activity from potential deviations. This anomaly-based approach to threat detection allows Darktrace to detect cyber threats as soon as they emerge.  

By combining DETECT with the autonomous response capabilities of RESPOND, Darktrace customers are able to effectively safeguard their digital environments and ensure that emerging threats can be identified and shut down at the earliest stage of the kill chain, regardless of the tactics employed by would-be attackers.

Credit to Piramol Krishnan, Cyber Analyst, Qing Hong Kwa, Senior Cyber Analyst & Deputy Team Lead, Singapore

Appendices

Darktrace Model Detections

  • Device / Increased External Connectivity
  • Device / Large Number of Connections to New Endpoints
  • Device / SMB Session Brute Force (Admin)
  • Compliance / External Windows Communications
  • Anomalous Connection / New or Uncommon Service Control
  • Compromise / Unusual SVCCTL Activity
  • Compromise / Rare Domain Pointing to Internal IP
  • Anomalous File / Masqueraded File Transfer

RESPOND Models

  • Antigena / Network / Significant Anomaly / Antigena Breaches Over Time Block
  • Antigena / Network / External Threat / Antigena Suspicious Activity Block
  • Antigena / Network / Significant Anomaly / Antigena Significant Anomaly from Client Block
  • Antigena / Network / Significant Anomaly / Antigena Enhanced Monitoring from Client Block
  • Antigena / Network / External Threat / Antigena Suspicious File Block
  • Antigena / Network / External Threat / Antigena File then New Outbound Block

List of IoCs

IoC - Type - Description

/C558B828.Png - URI - URI for Purple Fox Rootkit [4]

5b1de649f2bc4eb08f1d83f7ea052de5b8fe141f - File Hash - SHA1 hash of C558B828.Png file (Malware payload)

190.4.210[.]242 - IP - Purple Fox C2 Servers

218.4.170[.]236 - IP - IP for download of .PNG file (Malware payload)

180.169.1[.]220 - IP - IP for download of .PNG file (Malware payload)

103.94.108[.]114:10837 - IP - IP from Service Control MSIEXEC script to download PNG file (Malware payload)

221.199.171[.]174:16543 - IP - IP from Service Control MSIEXEC script to download PNG file (Malware payload)

61.222.155[.]49:14098 - IP - IP from Service Control MSIEXEC script to download PNG file (Malware payload)

178.128.103[.]246:17880 - IP - IP from Service Control MSIEXEC script to download PNG file (Malware payload)

222.134.99[.]132:12539 - IP - IP from Service Control MSIEXEC script to download PNG file (Malware payload)

164.90.152[.]252:18075 - IP - IP from Service Control MSIEXEC script to download PNG file (Malware payload)

198.199.80[.]121:11490 - IP - IP from Service Control MSIEXEC script to download PNG file (Malware payload)

MITRE ATT&CK Mapping

Tactic - Technique

Reconnaissance - Active Scanning T1595, Active Scanning: Scanning IP Blocks T1595.001, Active Scanning: Vulnerability Scanning T1595.002

Resource Development - Obtain Capabilities: Malware T1588.001

Initial Access, Defense Evasion, Persistence, Privilege Escalation - Valid Accounts: Default Accounts T1078.001

Initial Access - Drive-by Compromise T1189

Defense Evasion - Masquerading T1036

Credential Access - Brute Force T1110

Discovery - Network Service Discovery T1046

Command and Control - Proxy: External Proxy T1090.002

References

  1. https://blog.360totalsecurity.com/en/purple-fox-trojan-burst-out-globally-and-infected-more-than-30000-users/
  2. https://www.trendmicro.com/en_us/research/19/i/purple-fox-fileless-malware-with-rookit-component-delivered-by-rig-exploit-kit-now-abuses-powershell.html
  3. https://www.akamai.com/blog/security/purple-fox-rootkit-now-propagates-as-a-worm
  4. https://www.foregenix.com/blog/an-overview-on-purple-fox
  5. https://www.trendmicro.com/en_sg/research/21/j/purplefox-adds-new-backdoor-that-uses-websockets.html
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
Piramol Krishnan
Cyber Security 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

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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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