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June 10, 2024

Darktrace Investigation Into Medusa Ransomware

See how Darktrace empowers organizations to fight back against Medusa ransomware, enhancing their cybersecurity posture with advanced technology.
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
Maria Geronikolou
Cyber Analyst
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10
Jun 2024

What is Living off the Land attack?

In the face of increasingly vigilant security teams and adept defense tools, attackers are continually looking for new ways to circumvent network security and gain access to their target environments. One common tactic is the leveraging of readily available utilities and services within a target organization’s environment in order to move through the kill chain; a popular method known as living off the land (LotL). Rather than having to leverage known malicious tools or write their own malware, attackers are able to easily exploit the existing infrastructure of their targets.

The Medusa ransomware group in particular are known to extensively employ LotL tactics, techniques and procedures (TTPs) in their attacks, as one Darktrace customer in the US discovered in early 2024.

What is Medusa Ransomware?

Medusa ransomware (not to be confused with MedusaLocker) was first observed in the wild towards the end of 2022 and has been a popular ransomware strain amongst threat actors since 2023 [1]. Medusa functions as a Ransomware-as-a-Service (RaaS) platform, providing would-be attackers, also know as affiliates, with malicious software and infrastructure required to carry out disruptive ransomware attacks. The ransomware is known to target organizations across many different industries and countries around the world, including healthcare, education, manufacturing and retail, with a particular focus on the US [2].

How does Medusa Ransomware work?

Medusa affiliates are known to employ a number of TTPs to propagate their malware, most predominantly gaining initial access by exploiting vulnerable internet-facing assets and targeting valid local and domain accounts that are used for system administration.

The ransomware is typically delivered via phishing and spear phishing campaigns containing malicious attachments [3] [4], but it has also been observed using initial access brokers to access target networks [5]. In terms of the LotL strategies employed in Medusa compromises, affiliates are often observed leveraging legitimate services like the ConnectWise remote monitoring and management (RMM) software and PDQ Deploy, in order to evade the detection of security teams who may be unable to distinguish the activity from normal or expected network traffic [2].

According to researchers, Medusa has a public Telegram channel that is used by threat actors to post any data that may have been stolen, likely in an attempt to extort organizations and demand payment [2].  

Darktrace’s Coverage of Medusa Ransomware

Established Foothold and C2 activity

In March 2024, Darktrace / NETWORK identified over 80 devices, including an internet facing domain controller, on a customer network performing an unusual number of activities that were indicative of an emerging ransomware attack. The suspicious behavior started when devices were observed making HTTP connections to the two unusual endpoints, one of which is “go-sw6-02.adventos[.]de”, with the PowerShell and JWrapperDownloader user agents.

Darktrace’s Cyber AI Analyst™ launched an autonomous investigation into the connections and was able to connect the seemingly separate events into one wider incident spanning multiple different devices. This allowed the customer to visualize the activity in chronological order and gain a better understanding of the scope of the attack.

At this point, given the nature and rarity of the observed activity, Darktrace /NETWORK's autonomous response would have been expected to take autonomous action against affected devices, blocking them from making external connections to suspicious locations. However, autonomous response was not configured to take autonomous action at the time of the attack, meaning any mitigative actions had to be manually approved by the customer’s security team.

Internal Reconnaissance

Following these extensive HTTP connections, between March 1 and 7, Darktrace detected two devices making internal connection attempts to other devices, suggesting network scanning activity. Furthermore, Darktrace identified one of the devices making a connection with the URI “/nice ports, /Trinity.txt.bak”, indicating the use of the Nmap vulnerability scanning tool. While Nmap is primarily used legitimately by security teams to perform security audits and discover vulnerabilities that require addressing, it can also be leveraged by attackers who seek to exploit this information.

Darktrace / NETWORK model alert showing the URI “/nice ports, /Trinity.txt.bak”, indicating the use of Nmap.
Figure 1: Darktrace /NETWORK model alert showing the URI “/nice ports, /Trinity.txt.bak”, indicating the use of Nmap.

Darktrace observed actors using multiple credentials, including “svc-ndscans”, which was also seen alongside DCE-RPC activity that took place on March 1. Affected devices were also observed making ExecQuery and ExecMethod requests for IWbemServices. ExecQuery is commonly utilized to execute WMI Query Language (WQL) queries that allow the retrieval of information from WI, including system information or hardware details, while ExecMethod can be used by attackers to gather detailed information about a targeted system and its running processes, as well as a tool for lateral movement.

Lateral Movement

A few hours after the first observed scanning activity on March 1, Darktrace identified a chain of administrative connections between multiple devices, including the aforementioned internet-facing server.

Cyber AI Analyst was able to connect these administrative connections and separate them into three distinct ‘hops’, i.e. the number of administrative connections made from device A to device B, including any devices leveraged in between. The AI Analyst investigation was also able to link the previously detailed scanning activity to these administrative connections, identifying that the same device was involved in both cases.

Cyber AI Analyst investigation into the chain of lateral movement activity.
Figure 2: Cyber AI Analyst investigation into the chain of lateral movement activity.

On March 7, the internet exposed server was observed transferring suspicious files over SMB to multiple internal devices. This activity was identified as unusual by Darktrace compared to the device's normal SMB activity, with an unusual number of executable (.exe) and srvsvc files transferred targeting the ADMIN$ and IPC$ shares.

Cyber AI Analyst investigation into the suspicious SMB write activity.
Figure 3: Cyber AI Analyst investigation into the suspicious SMB write activity.
Graph highlighting the number of successful SMB writes and the associated model alerts.
Figure 4: Graph highlighting the number of successful SMB writes and the associated model alerts.

The threat actor was also seen writing SQLite3*.dll files over SMB using a another credential this time. These files likely contained the malicious payload that resulted in the customer’s files being encrypted with the extension “.s3db”.

Darktrace’s visibility over an affected device performing successful SMB writes.
Figure 5: Darktrace’s visibility over an affected device performing successful SMB writes.

Encryption of Files

Finally, Darktrace observed the malicious actor beginning to encrypt and delete files on the customer’s environment. More specifically, the actor was observed using credentials previously seen on the network to encrypt files with the aforementioned “.s3db” extension.

Darktrace’s visibility over the encrypted files.
Figure 6: Darktrace’s visibility over the encrypted files.


After that, Darktrace observed the attacker encrypting  files and appending them with the extension “.MEDUSA” while also dropping a ransom note with the file name “!!!Read_me_Medusa!!!.txt”

Darktrace’s detection of threat actors deleting files with the extension “.MEDUSA”.
Figure 7: Darktrace’s detection of threat actors deleting files with the extension “.MEDUSA”.
Darktrace’s detection of the Medusa ransom note.
Figure 8: Darktrace’s detection of the Medusa ransom note.

At the same time as these events, Darktrace observed the attacker utilizing a number of LotL techniques including SSL connections to “services.pdq[.]tools”, “teamviewer[.]com” and “anydesk[.]com”. While the use of these legitimate services may have bypassed traditional security tools, Darktrace’s anomaly-based approach enabled it to detect the activity and distinguish it from ‘normal’ network activity. It is highly likely that these SSL connections represented the attacker attempting to exfiltrate sensitive data from the customer’s network, with a view to using it to extort the customer.

Cyber AI Analyst’s detection of “services.pdq[.]tools” usage.
Figure 9: Cyber AI Analyst’s detection of “services.pdq[.]tools” usage.

If this customer had been subscribed to Darktrace's Proactive Threat Notification (PTN) service at the time of the attack, they would have been promptly notified of these suspicious activities by the Darktrace Security Operation Center (SOC). In this way they could have been aware of the suspicious activities taking place in their infrastructure before the escalation of the compromise. Despite this, they were able to receive assistance through the Ask the Expert service (ATE) whereby Darktrace’s expert analyst team was on hand to assist the customer by triaging and investigating the incident further, ensuring the customer was well equipped to remediate.  

As Darktrace /NETWORK's autonomous response was not enabled in autonomous response mode, this ransomware attack was able to progress to the point of encryption and data exfiltration. Had autonomous response been properly configured to take autonomous action, Darktrace would have blocked all connections by affected devices to both internal and external endpoints, as well as enforcing a previously established “pattern of life” on the device to stop it from deviating from its expected behavior.

Conclusion

The threat actors in this Medusa ransomware attack attempted to utilize LotL techniques in order to bypass human security teams and traditional security tools. By exploiting trusted systems and tools, like Nmap and PDQ Deploy, attackers are able to carry out malicious activity under the guise of legitimate network traffic.

Darktrace’s Self-Learning AI, however, allows it to recognize the subtle deviations in a device’s behavior that tend to be indicative of compromise, regardless of whether it appears legitimate or benign on the surface.

Further to the detection of the individual events that made up this ransomware attack, Darktrace’s Cyber AI Analyst was able to correlate the activity and collate it under one wider incident. This allowed the customer to track the compromise and its attack phases from start to finish, ensuring they could obtain a holistic view of their digital environment and remediate effectively.

[related-resource]

Appendices

Credit to Maria Geronikolou, Cyber Analyst, Ryan Traill, Threat Content Lead

Darktrace DETECT Model Detections

Anomalous Connection / SMB Enumeration

Device / Anomalous SMB Followed By Multiple Model Alerts

Device / Suspicious SMB Scanning Activity

Device / Attack and Recon Tools

Device / Suspicious File Writes to Multiple Hidden SMB Share

Compromise / Ransomware / Ransom or Offensive Words Written to SMB

Device / Internet Facing Device with High Priority Alert

Device / Network Scan

Anomalous Connection / Powershell to Rare External

Device / New PowerShell User Agent

Possible HTTP Command and Control

Extensive Suspicious DCE-RPC Activity

Possible SSL Command and Control to Multiple Endpoints

Suspicious Remote WMI Activity

Scanning of Multiple Devices

Possible Ransom Note Accessed over SMB

List of Indicators of Compromise (IoCs)

IoC – Type – Description + Confidence

207.188.6[.]17      -     IP address   -      C2 Endpoint

172.64.154[.]227 - IP address -        C2 Endpoint

go-sw6-02.adventos[.]de.  Hostname  - C2 Endpoint

.MEDUSA             -        File extension     - Extension to encrypted files

.s3db               -             File extension    -  Created file extension

SQLite3-64.dll    -        File           -               Used tool

!!!Read_me_Medusa!!!.txt - File -   Ransom note

Svc-ndscans         -         Credential     -     Possible compromised credential

Svc-NinjaRMM      -       Credential      -     Possible compromised credential

MITRE ATT&CK Mapping

Discovery  - File and Directory Discovery - T1083

Reconnaissance    -  Scanning IP            -          T1595.001

Reconnaissance -  Vulnerability Scanning -  T1595.002

Lateral Movement -Exploitation of Remote Service -  T1210

Lateral Movement - Exploitation of Remote Service -   T1210

Lateral Movement  -  SMB/Windows Admin Shares     -    T1021.002

Lateral Movement   -  Taint Shared Content          -            T1080

Execution   - PowerShell     - T1059.001

Execution  -   Service Execution   -    T1059.002

Impact   -    Data Encrypted for Impact  -  T1486

References

[1] https://unit42.paloaltonetworks.com

[2] https://thehackernews.com

[3] https://trustwave.com

[4] https://www.sangfor.com

[5] https://thehackernews.com

[6]https://any.run

Get the latest insights on emerging cyber threats

This report explores the latest trends shaping the cybersecurity landscape and what defenders need to know in 2026.

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
Maria Geronikolou
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
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