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January 5, 2023

BlackMatter's Smash-and-Grab Ransom Attack Incident Analysis

Stay informed on cybersecurity trends! Read about a BlackMatters ransom attack incident and Darktrace's analysis on how RESPOND could have stopped the attack.
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
The Darktrace Analyst Team
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05
Jan 2023

Only a few years ago, popular reporting announced that the days of smash-and-grab attacks were over and that a new breed of hackers were taking over with subtler, ‘low-and-slow’ tactics [1]. Although these have undoubtedly appeared, smash-and-grab have quickly become overlooked – perhaps with worrying consequences. Last year, Google saw repeated phishing campaigns using cookie theft malware and most recently, reports of hacktivists using similar techniques have been identified during the 2022 Ukraine Conflict [2 & 3]. Where did their inspiration come from? For larger APT groups such as BlackMatter, which first appeared in the summer of 2021, smash-and-grabs never went out of fashion.

This blog dissects a BlackMatter ransomware attack that hit an organization trialing Darktrace back in 2021. The case reveals what can happen when a security team does not react to high-priority alerts. 

When entire ransomware attacks can be carried out over the course of just 48 hours, there is a high risk to relying on security teams to react to detection notifications and prevent damage before the threat escalates. Although there has been hesitancy in its uptake [4], this blog also demonstrates the need for automated response solutions like Darktrace RESPOND.

The Name Game: Untangling BlackMatter, REvil, and DarkSide

Despite being a short-lived criminal organization on the surface [5], a number of parallels have now been drawn between the TTPs (Tactics, Techniques and Procedures) of the newer BlackMatter group and those of the retired REvil and DarkSide organizations [6]. 

Prior to their retirement, DarkSide and REvil were perhaps the biggest names in cyber-crime, responsible for two of last year’s most devastating ransomware attacks. Less than two weeks after the Colonial Pipeline attack, DarkSide announced it was shutting down its operation [7]. Meanwhile the FBI shutdown REvil in January 2022 after its devastating Fourth of July Kaseya attacks and a failed return in September [8]. It is now suspected that members from one or both went on to form BlackMatter.

This rebranding strategy parallels the smash-and-grab attacks these groups now increasingly employ: they make their money, and a lot of noise, and when they’re found out, they disappear before organizations or governments can pull together their threat intelligence and organize an effective response. When they return days, weeks or months later, they do so having implemented enough small changes to render themselves and their attacks unrecognizable. That is how DarkSide can become BlackMatter, and how its attacks can slip through security systems trained on previously encountered threats. 

Attack Details

In September 2021 Darktrace was monitoring a US marketing agency which became the victim of a double extortion ransomware attack that bore hallmarks of a BlackMatter operation. This began when a single domain-authenticated device joined the company’s network. This was likely a pre-infected company device being reconnected after some time offline. 

Only 15 minutes after joining, the device began SMB and ICMP scanning activities towards over 1000 different internal IPs. There was also a large spike of requests for Epmapper, which suggested an intent for RPC-based lateral movement. Although one credential was particularly prominent, multiple were used including labelled admin credentials. Given it’s unexpected nature, this recon quickly triggered a chain of DETECT/Network model breaches which ensured that Darktrace’s SOC were alerted via the Proactive Threat Notification service. Whilst SOC analysts began to triage the activity, the organization failed to act on any of the alerts they received, leaving the detected threat to take root within their digital environment. 

Shortly after, a series of C2 beaconing occurred towards an endpoint associated with Cobalt Strike [9]. This was accompanied by a range of anomalous WMI bind requests to svcctl, SecAddr and further RPC connections. These allowed the initial compromised device to quickly infect 11 other devices. With continued scanning over the next day, valuable data was soon identified. Across several transfers, 230GB of internal data was then exfiltrated from four file servers via SSH port 22. This data was then made unusable to the organization through encryption occurring via SMB Writes and Moves/Renames with the randomly generated extension ‘.qHefKSmfd’. Finally a ransom note titled ‘qHefKSmfd.README.txt’ was dropped.

This ransom note was appended with the BlackMatter ASCII logo:

Figure 1- The ASCII logo which accompanied BlackMatter’s ransom note

Although Darktrace DETECT and Cyber AI Analyst continued to provide live alerting, the actor successfully accomplished their mission.  

There are numerous reasons that an organization may fail to organize a response to a threat, (including resource shortages, out of hours attacks, and groups that simply move too fast). Without Darktrace’s RESPOND capabilities enabled, the threat actors could proceed this attack without obstacles. 

Figure 2- Cyber AI Analyst breaks down the stages of the attack [Note: this screenshot is from V5 of DETECT/Network] 

How would the attack have unfolded with RESPOND?

Armed with Darktrace’s evolving knowledge of ‘self’ for the customer’s unique digital environment, RESPOND would have activated within seconds of the first network scan, which was recognized as highly anomalous. The standard action taken here would usually involve enforcing the standard ‘pattern of life’ for the compromised device over a set time period in order to halt the anomaly while allowing the business to continue operating as normal.

RESPOND constantly re-evaluates threats as attacks unfold. Had the first stage still been successful, it would have continued to take targeted action at each corresponding stage of this attack. RESPOND models would have alerted to block the external connections to C2 servers over port 443, the outbound exfil attempts and crucially the SMB write activity over port 445 related to encryption.

As DETECT and RESPOND feed into one another, Darktrace would have continued to assess its actions as BlackMatter pivoted tactics. These actions buy back critical time for security teams that may not be in operation over the weekend, and stun the attacker into place without applying overly aggressive responses that create more problems than they solve.

Ultimately although this incident did not resolve autonomously, in response to the ransom event, Darktrace offered to enable RESPOND and set it in active mode for ransomware indicators across all client and server devices. This ensured an event like this would not occur again. 

Why does RESPOND work?

Response solutions must be accurate enough to fire only when there is a genuine threat, configurable enough to let the user stay in the driver’s seat, and intelligent enough to know the right action to take to contain only the malicious activity- without disrupting normal business operations. 

This is only possible if you can establish what ‘normal’ is for any one organization. And this is how Darktrace’s RESPOND product family ensures its actions are targeted and proportionate. By feeding off DETECT alerting which highlights subtle or large deviations across the network, cloud and SaaS, RESPOND can provide a measured response to the potential threat. This includes actions such as:

  • Enforcing the device’s ‘pattern of life’ for a given length of time 
  • Enforcing the ‘group pattern of life’ (stopping a device from doing anything its peers haven’t done in the past)
  • Blocking connections of a certain type to a certain destination
  • Logging out of a cloud account 
  • ‘Smart quarantining’ an endpoint device- maintaining access to VPNs and company’s AV solution

Conclusion 

In its report on BlackMatter [10], CISA recommended that organizations invest in network monitoring tools with the capacity to investigate anomalous activity. Picking up on unusual behavior rather than predetermined rules and signatures is an important step in fighting back against new threats. As this particular story shows, however, detection alone is not always enough. Turning on RESPOND, which takes immediate and precise action to contain threats, regardless of when and where they come in, is the best way to counter smash-and-grab attacks and protect organizations’ digital assets. There is little doubt that the threat actors behind BlackMatter will or have already returned with new names and strategies- but organizations with RESPOND will be ready for them.

Appendices

Darktrace Model Detections (in order of breach)

Those with the ‘PTN’ prefix were alerted directly to Darktrace’s 24/7 SOC team.

  • Device / ICMP Address Scan
  • Device / Suspicious SMB Scanning Activity
  • (PTN) Device / Suspicious Network Scan Activity
  • Anomalous Connection / SMB Enumeration
  • Device / Possible RPC Lateral Movement
  • Device / Active Directory Reconnaissance
  • Unusual Activity / Possible RPC Recon Activity
  • Device / Possible SMB/NTLM Reconnaissance
  • Compliance / Default Credential Usage
  • Device / New or Unusual Remote Command Execution
  • Anomalous Connection / New or Uncommon Service Control
  • Device / New or Uncommon SMB Named Pipe
  • Device / SMB Session Bruteforce
  • Device / New or Uncommon WMI Activity
  • (PTN) Device / Multiple Lateral Movement Model Breaches
  • Compromise / Sustained SSL or HTTP Increase
  • Compromise / SSL or HTTP Beacon
  • Compromise / Sustained TCP Beaconing Activity To Rare Endpoint
  • Device / Anomalous SMB Followed By Multiple Model Breaches
  • Device / Anomalous RDP Followed By Multiple Model Breaches
  • Anomalous Server Activity / Rare External from Server
  • Anomalous Connection / Anomalous SSL without SNI to New External
  • Anomalous Connection / Rare External SSL Self-Signed
  • Device / Long Agent Connection to New Endpoint
  • Compliance / SMB Drive Write
  • Anomalous Connection / Unusual Admin SMB Session
  • Anomalous Connection / High Volume of New or Uncommon Service Control
  • Anomalous Connection / Unusual Admin RDP Session
  • Device / Suspicious File Writes to Multiple Hidden SMB Shares
  • Anomalous Connection / Multiple Connections to New External TCP Port
  • Compliance / SSH to Rare External Destination
  • Anomalous Connection / Uncommon 1 GiB Outbound
  • Anomalous Connection / Data Sent to Rare Domain
  • Anomalous Connection / Download and Upload
  • (PTN) Unusual Activity / Enhanced Unusual External Data Transfer
  • Anomalous File / Internal / Additional Extension Appended to SMB File
  • (PTN) Compromise / Ransomware / Suspicious SMB Activity

List of IOCs 

Reference List 

[1] https://www.designnews.com/industrial-machinery/new-age-hackers-are-ditching-smash-and-grab-techniques 

[2] https://cybernews.com/cyber-war/how-do-smash-and-grab-cyberattacks-help-ukraine-in-waging-war/

[3] https://blog.google/threat-analysis-group/phishing-campaign-targets-youtube-creators-cookie-theft-malware/

[4] https://www.ukcybersecuritycouncil.org.uk/news-insights/articles/the-benefits-of-automation-to-cyber-security/

[5] https://techcrunch.com/2021/11/03/blackmatter-ransomware-shut-down/ 

[6] https://www.trellix.com/en-us/about/newsroom/stories/research/blackmatter-ransomware-analysis-the-dark-side-returns.html

[7] https://www.nytimes.com/2021/05/14/business/darkside-pipeline-hack.html

[8] https://techcrunch.com/2022/01/14/fsb-revil-ransomware/ 

[9] https://www.virustotal.com/gui/domain/georgiaonsale.com/community

[10] https://www.cisa.gov/uscert/ncas/alerts/aa21-291a

Credit to: Andras Balogh, SOC Analyst and Gabriel Few-Wiegratz, Threat Intelligence Content Production Lead

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
The Darktrace Analyst Team

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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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