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February 11, 2025

Defending Against Living-off-the-Land Attacks: Anomaly Detection in Action

Discover how Darktrace detected and responded to cyberattacks using Living-off-the-Land (LOTL) tactics to exploit trusted services and tools on customer networks.
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
Alexandra Sentenac
Cyber Analyst
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11
Feb 2025

What is living-off-the-land?

Threat actors employ a variety of techniques to compromise target networks, including exploiting unpatched vulnerabilities, abusing misconfigurations, deploying backdoors, and creating custom malware. However, these methods generate a lot of noise and are relatively easy for network and host-based monitoring tools to detect, especially once indicators of compromise (IoCs) and tactics, techniques, and procedures (TTPs) are published by the cybersecurity community.

Living-off-the-Land (LOTL) techniques, however, allow attacks to remain nearly invisible to Endpoint Detection and Response (EDR) tools – leveraging trusted protocols, applications and native systems to carry out malicious activity. While mitigations exist, they are often poorly implemented. The Cybersecurity and Infrastructure Security Agency (CISA) found that some organizations “lacked security baselines, allowing [Living-off-the-Land binaries (LOLBins)] to execute and leaving analysts unable to identify anomalous activity” and “organizations did not appropriately tune their detection tools to reduce alert noise, leading to an unmanageable level of alerts to sift through and action" [1].

Darktrace / NETWORK addresses this challenge across Information Technology (IT), Operational Technology (OT), and cloud environments by continuously analyzing network traffic and identifying deviations from normal behavior with its multi-layered AI – helping organizations detect and respond to LOTL attacks in real time.

Darktrace’s detection of LOTL attacks

This blog will review two separate attacks detected by Darktrace that leveraged LOTL techniques at several stages of the intrusion.

Case A

Reconnaissance

In September 2024, a malicious actor gained access to a customer network via their Virtual Private Network (VPN) from two desktop devices that had no prior connection history. Over two days, the attacker conducted multiple network scans, targeting ports associated with Remote Desktop Protocol (RDP) and NTLM authentication. Darktrace detected this unusual activity, triggering multiple alerts for scanning and enumeration activity.

Unusual NTLM authentication attempts using default accounts like “Guest” and “Administrator” were detected. Two days after the initial intrusion, suspicious DRSGetNCChanges requests were observed on multiple domain controllers (DCs), targeting the Directory Replication Service RPC interface (i.e., drsuapi) – a technique used to extract account hashes from DCs. This process can be automated using tools like Mimikatz's DcSync and DCShadow

Around the same time, attacker-controlled devices were seen presenting an admin credential and another credential potentially granting access to Cisco Firewall systems, suggesting successful privilege escalation. Due to the severity of this activity, Darktrace’s Autonomous Response was triggered to prevent the device from further deviation from its normal behavior. However, because Autonomous Response was configured in Human Confirmation mode, the response actions had to be manually applied by the customer.

Cyber AI Analyst Critical Incident showing the unusual DRSGetNCChanges requests following unusual scanning activity.
Figure 1: Cyber AI Analyst Critical Incident showing the unusual DRSGetNCChanges requests following unusual scanning activity.

Lateral movement

Darktrace also detected anomalous RDP connections to domain controllers, originating from an attacker-controlled device using admin and service credentials. The attacker then successfully pivoted to a likely RDP server, leveraging the RDP protocol – one of the most commonly used for lateral movement in network compromises observed by Darktrace.

Cyber Analyst Incident displaying unusual RDP lateral movement connections
Figure 2: Cyber Analyst Incident displaying unusual RDP lateral movement connections.

Tooling

Following an incoming RDP connection, one of the DCs made a successful GET request to the URI '/download/122.dll' on the 100% rare IP, 146.70.145[.]189. The request returned an executable file, which open-source intelligence (OSINT) suggests is likely a CobaltStrike C2 sever payload [2] [3]. Had Autonomous Response been enabled here, it would have blocked all outgoing traffic from the DC allowing the customer to investigate and remediate.

Additionally, Darktrace detected a suspicious CreateServiceW request to the Service Control (SVCCTL) RPC interface on a server. The request executed commands using ‘cmd.exe’ to perform the following actions

  1. Used ‘tasklist’ to filter processes named ”lsass.exe” (Local Security Authority Subsystem Service) to find its specific process ID.
  2. Used “rundll32.exe” to execute the MiniDump function from the “comsvcs.dll” library, creating a memory dump of the “lsass.exe” process.
  3. Saved the output to a PNG file in a temporary folder,

Notably, “cmd.exe” was referenced as “CMd.EXE” within the script, likely an attempt to evade detection by security tools monitoring for specific keywords and patterns.

Model Alert Log showing the unusual SVCCTL create request.
Figure 3: Model Alert Log showing the unusual SVCCTL create request.

Over the course of three days, this activity triggered around 125 Darktrace / NETWORK alerts across 11 internal devices. In addition, Cyber AI Analyst launched an autonomous investigation into the activity, analyzing and connecting 16 separate events spanning multiple stages of the cyber kill chain - from initial reconnaissance to payload retrieval and lateral movement.

Darktrace’s comprehensive detection enabled the customer’s security team to remediate the compromise before any further escalation was observed.

Case B

Between late 2023 and early 2024, Darktrace identified a widespread attack that combined insider and external threats, leveraging multiple LOTL tools for reconnaissance and lateral movement within a customer's network.

Reconnaissance

Initially, Darktrace detected the use of a new administrative credential by a device, which then made unusual RDP connections to multiple internal systems, including a 30-minute connection to a DC. Throughout the attack, multiple unusual RDP connections using the new administrative credential “%admin!!!” were observed, indicating that this protocol was leveraged for lateral movement.

The next day, a Microsoft Defender Security Integration alert was triggered on the device due to suspicious Windows Local Security Authority Subsystem Service (LSASS) credential dump behavior. Since the LSASS process memory can store operating system and domain admin credentials, obtaining this sensitive information can greatly facilitate lateral movement within a network using legitimate tools such as PsExec or Windows Management Instrumentation (WMI) [4]. Security integrations with other security vendors like this one can provide insights into host-based processes, which are typically outside of Darktrace’s coverage. Darktrace’s anomaly detection and network activity monitoring help prioritize the investigation of these alerts.

Three days later, the attacker was observed logging into the DC and querying tickets for the Lightweight Directory Access Protocol (LDAP) service using the default credential “Administrator.” This activity, considered new by Darktrace, triggered an Autonomous Response action that blocked further connections on Kerberos port 88 to the DC. LDAP provides a central location to access and manage data about computers, servers, users, groups, and policies within a network. LDAP enumeration can provide valuable Active Directory (AD) object information to an attacker, which can be used to identify critical attack paths or accounts with high privileges.

Lateral movement

Following the incoming RDP connection, the DC began scanning activities, including RDP and Server Block Message (SMB) services, suggesting the attacker was using remote access for additional reconnaissance. Outgoing RDP connection attempts to over 100 internal devices were observed, with around 5% being successful, highlighting the importance of this protocol for the threat actor’s lateral movement.

Around the same time, the DC made WMI, PsExec, and service control connections to two other DCs, indicating further lateral movement using native administrative protocols and tools. These functions can be leveraged by attackers to query system information, run malicious code, and maintain persistent access to compromised devices while avoiding traditional security tool alarms. In this case, requested services included the IWbemServices (used to access WMI services) and IWbemFetchSmartEnum (used to retrieve a network-optimized enumerator interface) interfaces, with ExecQuery operations detected for the former. This method returns an enumerable collection of IWbemClassObject interface objects based on a query.

Additionally, unusual Windows Remote Management (WinRM) connections to another domain controller were observed. WinRM is a Microsoft protocol that allows systems to exchange and access management information over HTTP(S) across a network, such as running executables or modifying the registry and services.

Cyber AI Analyst Incident showing unusual WMI activity between the two DCs.
Figure 4: Cyber AI Analyst Incident showing unusual WMI activity between the two DCs.

The DC was also detected writing the file “PSEXESVC.exe” to the “ADMIN$” share of another internal device over the SMB file transfer network protocol. This activity was flagged as highly unusual by Darktrace, as these two devices had not previously engaged in this type of SMB connectivity.

It is rare for an attacker to immediately find the information or systems they are after, making it likely they will need to move around the network before achieving their objectives. Tools such as PsExec enable attackers to do this while largely remaining under the radar. With PsExec, attackers who gain access to a single system can connect to and execute commands remotely on other internal systems, access sensitive information, and spread their attack further into the environment.

Model Alert Event Log showing the new write of the file “PSEXESVC.exe” by one of the compromised devices over an SMB connection initiated at an unusual time.
Figure 5. Model Alert Event Log showing the new write of the file “PSEXESVC.exe” by one of the compromised devices over an SMB connection initiated at an unusual time.

Darktrace further observed the DC connecting to the SVCCTL endpoint on a remote device and performing the CreateServiceW operation, which was flagged as highly unusual based on previous behavior patterns between the two devices. Additionally, new ChangeServiceConfigW operations were observed from another device.

Aside from IWbemServices requests seen on multiple devices, Darktrace also detected multiple internal devices connecting to the ITaskSchedulerService interface over DCE-RPC and performing new SchRpcRegisterTask operations, which register a task on the destination system. Attackers can exploit the task scheduler to facilitate the initial or recurring execution of malicious code by a trusted system process, often with elevated permissions. The creation of these tasks was considered new or highly unusual and triggered several anomalous ITaskScheduler activity alerts.

Conclusion

As pointed out by CISA, threat actors frequently exploit the lack of implemented controls on their target networks, as demonstrated in the incidents discussed here. In the first case, VPN access was granted to all domain users, providing the attacker with a point of entry. In the second case, there were no restrictions on the use of RDP within the targeted network segment, allowing the attackers to pivot from device to device.

Darktrace assists security teams in monitoring for unusual use of LOTL tools and protocols that can be leveraged by threat actors to achieve a wide range of objectives. Darktrace’s Self-Learning AI sifts through the network traffic noise generated by these trusted tools, which are essential to administrators and developers in their daily tasks, and highlights any anomalous and potentially unexpected use.

Credit to Alexandra Sentenac (Senior Cyber Analyst) and Ryan Traill (Analyst Content Lead)

References

[1] https://www.cisa.gov/sites/default/files/2024-02/Joint-Guidance-Identifying-and-Mitigating-LOTL_V3508c.pdf

[2] https://www.virustotal.com/gui/ip-address/146.70.145.189/community

[3] https://www.virustotal.com/gui/file/cc9a670b549d84084618267fdeea13f196e43ae5df0d88e2e18bf5aa91b97318

[4]https://www.microsoft.com/en-us/security/blog/2022/10/05/detecting-and-preventing-lsass-credential-dumping-attacks

MITRE Mapping

INITIAL ACCESS - External Remote Services

DISCOVERY - Remote System Discovery

DISCOVERY - Network Service Discovery

DISCOVERY - File and Directory Discovery

CREDENTIAL ACCESS – OS Credential Dumping: LSASS Memory

LATERAL MOVEMENT - Remote Services: Remote Desktop Protocol

LATERAL MOVEMENT - Remote Services: SMB/Windows Admin Shares

EXECUTION - System Services: Service Execution

PERSISTENCE - Scheduled Task

COMMAND AND CONTROL - Ingress Tool Transfer

Darktrace Model Detections

Case A

Device / Suspicious Network Scan Activity

Device / Network Scan

Device / ICMP Address Scan

Device / Reverse DNS Sweep

Device / Suspicious SMB Scanning Activity

Device / Possible SMB/NTLM Reconnaissance

Anomalous Connection / Unusual Admin SMB Session

Device / SMB Session Brute Force (Admin)

Device / Possible SMB/NTLM Brute Force

Device / SMB Lateral Movement

Device / Anomalous NTLM Brute Force

Anomalous Connection / SMB Enumeration

Device / SMB Session Brute Force (Non-Admin)

Device / Anomalous SMB Followed By Multiple Model Breaches

Anomalous Connection / Possible Share Enumeration Activity

Device / RDP Scan

Device / Anomalous RDP Followed By Multiple Model Breaches

Anomalous Connection / Unusual Admin RDP Session

Anomalous Connection / Active Remote Desktop Tunnel

Anomalous Connection / Anomalous DRSGetNCChanges Operation

Anomalous Connection / High Priority DRSGetNCChanges

Compliance / Default Credential Usage

User / New Admin Credentials on Client

User / New Admin Credentials on Server

Device / Large Number of Model Breaches from Critical Network Device

User / New Admin Credential Ticket Request

Compromise / Unusual SVCCTL Activity

Anomalous Connection / New or Uncommon Service Control

Anomalous File / Script from Rare External Location

Anomalous Server Activity / Anomalous External Activity from Critical Network Device

Anomalous File / EXE from Rare External Location

Anomalous File / Numeric File Download

Device / Initial Breach Chain Compromise

Device / Multiple Lateral Movement Model Breaches

Device / Large Number of Model Breaches

Compromise / Multiple Kill Chain Indicators

Case B

User / New Admin Credentials on Client

Compliance / Default Credential Usage

Anomalous Connection / SMB Enumeration

Device / Suspicious SMB Scanning Activity

Device / RDP Scan

Device / New or Uncommon WMI Activity

Device / Anomaly Indicators / New or Uncommon WMI Activity Indicator

Device / New or Unusual Remote Command Execution

Anomalous Connection / New or Uncommon Service Control

Anomalous Connection / Active Remote Desktop Tunnel

Compliance / SMB Drive Write

Anomalous Connection / Anomalous DRSGetNCChanges Operation

Device / Multiple Lateral Movement Model Breaches

Device / Anomalous ITaskScheduler Activity

Anomalous Connection / Unusual Admin RDP Session

Device / Large Number of Model Breaches from Critical Network Device

Compliance / Default Credential Usage

IOC - Type - Description/Probability

146.70.145[.]189 - IP Address - Likely C2 Infrastructure

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
Alexandra Sentenac
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

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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
Your data. Our AI.
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