Blog
/
/
April 8, 2026

How to Secure AI and Find the Gaps in Your Security Operations

As AI adoption accelerates, security teams face growing risk across interconnected systems. This blog explores why siloed tools fall short, how lifecycle thinking helps, and how to ensure your security functions work together.
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
Nabil Zoldjalali
VP, Field CISO
secuing AI testing gaps security operationsDefault blog image
08
Apr 2026

Key takeaways

  • Securing enterprise AI requires both AI-specific controls and a strong security operations foundation across identity, SaaS, cloud, email, endpoints, networks, and data.
  • AI increases the speed and interconnectedness of risk, making it harder for siloed tools and sequential investigation processes to contain incidents quickly.
  • Security teams should test whether risk context, behavioral signals, investigations, and response actions can move effectively between domains and tools.
  • A mature security stack should support cross-domain correlation, early detection of suspicious intent, unified investigation, bounded automated response, and closed-loop remediation.
  • Organizations should strengthen security operations while introducing dedicated protections for AI models, agents, prompts, applications, data, and Shadow AI—not treat these as separate or sequential initiatives.

Why does securing AI require coordinated security operations?

Securing enterprise AI requires more than a AI-specific controls. Because AI systems interact with identities, applications, cloud services, sensitive data, and automated workflows, organizations need AI governance and visibility alongside coordinated detection, investigation, response, and remediation across the wider environment.

Security teams are under growing pressure to “secure AI” at the same pace which businesses are adopting it. But in many organizations, adoption is outpacing the ability to govern, monitor, and control it. When that gap widens, decision-making shifts from deliberate design to immediate coverage. The priority becomes getting something in place, whether that’s a point solution, a governance layer, or an extension of an existing platform, rather than ensuring those choices work together.

At the same time, AI governance is lagging adoption. 37% of organizations still lack AI adoption policies, shadow AI usage across SaaS has surged, and there are notable spikes in anomalous data uploads to generative AI services.  

First and foremost, it’s important to recognize the dual nature of AI risk. Much of the industry has focused on how attackers will use AI to move faster, scale campaigns, and evade detection. But what’s becoming just as significant is the risk introduced by AI inside the organization itself. Enterprises are rapidly embedding AI into workflows, SaaS platforms, and decision-making processes, creating new pathways for data exposure, privilege misuse, and unintended access across an already interconnected environment.

Because the introduction of complex AI systems into modern, hybrid environments is reshaping attacker behavior and exposing gaps between security functions, the challenge is no longer just having the right capabilities in place but effectively coordinating prevention, detection, investigation, response, and remediation together. As threats accelerate and systems become more interconnected, security depends on coordinated execution, not isolated tools, which is why lifecycle-based approaches to governance, visibility, behavioral oversight, and real-time control are gaining traction.

What can security teams learn from cloud security consolidation?

Cloud security showed that posture and runtime protection are most effective when they operate together. AI creates a similar challenge across even more domains: models, agents, identities, applications, data, and infrastructure. Siloed controls may identify individual issues, but coordinated operations are needed to understand and contain the complete sequence.

We have seen a version of AI adoption before in cloud security. In the early days, tooling fragmented into posture, workload/runtime, identity, data, and more. Gradually, cloud security collapsed into broader cloud platforms. The lesson was clear: posture without runtime misses active threats; runtime without posture ignores root causes. Strong programs ran both in parallel and stitched the findings together in operations.  

Today’s AI wave stretches that lesson across every domain. Adversaries are compressing “time‑to‑tooling” using LLM‑assisted development (“vibecoding”) and recycling public PoCs at unprecedented speed. That makes it difficult to secure through siloed controls, because the risk is not confined to one layer. It emerges through interactions across layers.

Keep in mind, most modern attacks don’t succeed by defeating a single control. They succeed by moving through the gaps between systems faster than teams can connect what they are seeing. Recent exploitation waves like React2Shell show how quickly opportunistic actors operationalize fresh disclosures and chain misconfigurations to monetize at scale.

In the React2Shell window, defenders observed rapid, opportunistic exploitation and iterative payload diversity across a broad infrastructure footprint, strains that outpace signature‑first thinking.  

You can stay up to date on attacker behavior by signing up for our newsletter where Darktrace’s threat research team and analyst community regularly dive deep into threat finds.

Ultimately, speed met scale in the cloud era; AI adds interconnectedness and orchestration. Simple questions — What happened? Who did it? Why? How? Where else? — now cut across identities, SaaS agents, model/service endpoints, data egress, and automated actions. The longer it takes to answer, the worse the blast radius becomes.

Why does AI increase the need for an integrated security platform?

An integrated security platform helps teams connect behavioral signals across identity, SaaS, cloud, network, endpoint, and email. This shared context supports earlier detection, faster cross-domain investigation, and bounded automated response. In AI-era attacks, the advantage comes from acting across the attack path in parallel rather than handling isolated alerts in sequence.

Think of security fusion as the connective tissue that lets you prevent, detect, investigate, and remediate in parallel, not in sequence. In practice, that looks like:

  1. Unified telemetry with behavioral context across identities, SaaS, cloud, network, endpoints, and email—so an anomalous action in one plane automatically informs expectations in others. (Inside‑the‑SOC investigations show this pays off when attacks hop fast between domains.)  
  1. Pre‑CVE and “in‑the‑wild” awareness feeding controls before signatures—reducing dwell time in fast exploitation windows.  
  1. Automated, bounded response that can contain likely‑malicious actions at machine speed without breaking workflows—buying analysts time to investigate with full context. (Rapid CVE coverage and exploit‑wave posts illustrate how critical those first minutes are.)  
  1. Investigation workflows that assume AI is in the loop—for both defenders and attackers. As adversaries adopt “agentic” patterns, investigations need graph‑aware, sequence‑aware reasoning to prioritize what matters early.

This isn’t theoretical. It’s reflected in the Darktrace posts that consistently draw readership: timely threat intel with proprietary visibility and executive frameworks that transform field findings into operating guidance.  

The five questions that matter (and the one that matters more)

When alerted to malicious or risky AI use, you’ll ask:

  1. What happened?
  1. Who did it?
  1. Why did they do it?
  1. How did they do it?
  1. Where else can this happen?

The sixth, more important question is: How much worse does it get while you answer the first five? The answer depends on whether your controls operate in sequence (slow) or in fused parallel (fast).

What to watch next: How the AI security market will likely evolve

Security markets tend to follow a familiar pattern. New technologies drive an initial wave of specialized tools (posture, governance, observability) each focused on a specific part of the problem. Over time, those capabilities consolidate as organizations realize the new challenge is coordination.

AI is accelerating the shift of focus to coordination because AI-powered attackers can move faster and operate across more systems at once. Recent exploitation waves show exactly this. Adversaries can operationalize new techniques and move across domains, turning small gaps into full attack paths.

Anticipate a continued move toward more integrated security models because fragmented approaches can’t keep up with the speed and interconnected nature of modern attacks.

What should an enterprise AI security architecture include?

An enterprise AI security architecture should connect AI-specific governance and visibility with cross-domain detection, investigation, response, and remediation. Identity, SaaS, cloud, email, endpoint, network, and data controls should be able to share context and coordinate action across the wider environment.

To assess whether a security stack is ready for AI, test how effectively signals, risk context, investigations, and response actions move across tools. A mature stack should correlate cross-domain activity, reconstruct multi-stage incidents, detect suspicious intent early, automate bounded containment, and connect response with remediation.

AI doesn’t create new surfaces as much as it exposes the fragility of the seams that already exist.  

Darktrace’s own public investigations consistently show that modern attacks, from LinkedIn‑originated phishing that pivots into corporate SaaS to multi‑stage exploitation waves like BeyondTrust CVE‑2026‑1731 and React2Shell, succeed not because a single control failed, but because no control saw the whole sequence, or no system was able to respond at the speed of escalation.  

Before thinking about “AI security,” customers should ensure they’ve built a security foundation where visibility, signals, and responses can pass cleanly between domains. That requires pressure‑testing the seams.

Below are the key integration questions and stack‑maturity tests every organization should run.

1. Do your security tools share risk context across domains?

Integration questions

  • When an identity behaves strangely (impossible travel, atypical OAuth grants), does that signal automatically inform your email, SaaS, cloud, and endpoint tools?
  • Do your tools normalize events in a way that lets you correlate identity → app → data → network without human stitching?

Why it matters

Darktrace’s public SOC investigations repeatedly show attackers starting in an unmonitored domain, then pivoting into monitored ones, such as phishing on LinkedIn that bypassed email controls but later appeared as anomalous SaaS behavior.

If tools can’t share or interpret each other's context, AI‑era attacks will outrun every control.

Tests you can run

  1. Shadow Identity Test
  • Create a temporary identity with no history.
  • Perform a small but unusual action: unusual browser, untrusted IP, odd OAuth request.
  • Expected maturity signal: other tools (email/SaaS/network) should immediately score the identity as high‑risk.
  1. Context Propagation Test
  • Trigger an alert in one system (e.g., endpoint anomaly) and check if other systems automatically adjust thresholds or sensitivity.
  • Low maturity signal: nothing changes unless an analyst manually intervenes.

2. Does detection trigger coordinated action, or does everything act alone?

Integration questions

  • When one system blocks or contains something, do other systems automatically tighten, isolate, or rate‑limit?
  • Does your stack support bounded autonomy — automated micro‑containment without broad business disruption?

Why it matters

In public cases like BeyondTrust CVE‑2026‑1731 exploitation, Darktrace observed rapid C2 beaconing, unusual downloads, and tunneling attempts across multiple systems. Containment windows were measured in minutes, not hours.  

Tests you can run

  1. Chain Reaction Test
  • Simulate a primitive threat (e.g., access from TOR exit node).
  • Your identity provider should challenge → email should tighten → SaaS tokens should re‑authenticate.
  • Weak seam indicator: only one tool reacts.
  1. Autonomous Boundary Test
  • Induce a low‑grade anomaly (credential spray simulation).
  • Evaluate whether automated containment rules activate without breaking legitimate workflows.

3. Can your team investigate a cross‑domain incident without swivel‑chairing?

Integration questions

  • Can analysts pivot from identity → SaaS → cloud → endpoint in one narrative, not five consoles?
  • Does your investigation tooling use graphs or sequence-based reasoning, or is it list‑based?

Why it matters

Darktrace’s Cyber AI Analyst and DIGEST research highlights why investigations must interpret structure and progression, not just standalone alerts. Attackers now move between systems faster than human triage cycles.  

Tests you can run

  1. One‑Hour Timeline Build Test
  • Pick any detection.
  • Give an analyst one hour to produce a full sequence: entry → privilege → movement → egress.
  • Weak seam indicator: they spend >50% of the hour stitching exports.
  1. Multi‑Hop Replay Test
  • Simulate an incident that crosses domains (phish → SaaS token → data access).
  • Evaluate whether the investigative platform auto‑reconstructs the chain.

4. Do you detect intent or only outcomes?

Integration questions

  • Can your stack detect the setup behaviors before an attack becomes irreversible?
  • Are you catching pre‑CVE anomalies or post‑compromise symptoms?

Why it matters

Darktrace publicly documents multiple examples of pre‑CVE detection, where anomalous behavior was flagged days before vulnerability disclosure. AI‑assisted attackers will hide behind benign‑looking flows until the very last moment.

Tests you can run

  1. Intent‑Before‑Impact Test
  • Simulate reconnaissance-like behavior (DNS anomalies, odd browsing to unknown SaaS, atypical file listing).
  • Mature systems will flag intent even without an exploit.
  1. CVE‑Window Test
  • During a real CVE patch cycle, measure detection lag vs. public PoC release.
  • Weak seam indicator: your detection rises only after mass exploitation begins.

5. Are response and remediation connected?

Integration questions

  • When you contain something, does that trigger root-cause remediation workflows in identity, cloud config, or SaaS posture?
  • Does fixing a misconfiguration automatically update correlated controls?

Why it matters

Darktrace’s cloud investigations (e.g., cloud compromise analysis) emphasize that remediation must close both runtime and posture gaps in parallel.

Tests you can run

  1. Closed‑Loop Remediation Test
  • Introduce a small misconfiguration (over‑permissioned identity).
  • Trigger an anomaly.
  • Mature stacks will: detect → contain → recommend or automate posture repair.
  1. Drift‑Regression Test
  • After remediation, intentionally re‑introduce drift.
  • The system should immediately recognize deviation from known‑good baseline.

6. Do your security controls share a consistent behavioral baseline?

Integration questions

  • Is “normal behavior” defined in one place or many?
  • Do baselines update globally or per-tool?

Why it matters

Attackers (including AI‑assisted ones) increasingly exploit misaligned baselines, behaving “normal” to one system and anomalous to another.

Tests you can run

  1. Baseline Drift Test
  • Change the behavior of a service account for 24 hours.
  • Mature platforms will flag the deviation early and propagate updated expectations.
  1. Cross‑Domain Baseline Consistency Test
  • Compare identity’s risk score vs. cloud vs. SaaS.
  • Weak seam indicator: risk scores don’t align.

Build a stronger foundation for secure AI

Security teams should focus on how effectively their stack operates as one system before AI adds further pressure to the gaps between controls. Organizations should strengthen cross-domain detection, correlation, investigation, and response while introducing dedicated protections for AI models, agents, prompts, data, and workflows.

Darktrace / SECURE AI helps organizations gain visibility into how AI is being used across the enterprise, identify emerging risks, and apply behavioral oversight and real-time control across human and machine interactions.

Explore Securing AI in the Enterprise to learn how Darktrace can help your organization adopt and scale AI more securely.

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
Nabil Zoldjalali
VP, Field CISO

More in this series

No items found.

Blog

/

Network

/

August 7, 2026

When AI Agents Attack: The Case for Behavioral Anomaly Detection

Default blog imageDefault blog image

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.

This is the approach Darktrace has taken for years: learning what is normal across an organization’s digital environment, identifying meaningful deviations, and responding to emerging threats without relying on known attack signatures. As autonomous AI agents introduce new and unpredictable behaviors, that foundation becomes increasingly important to securing the enterprise.

Read the full report from the UK AI Security Institute here.

Continue reading
About the author
Adam Stevens
Senior Director of Product | Darktrace

Blog

/

/

August 5, 2026

Testing a Prompt injection Attack Against an Enterprise AI Agent

prompt injectionDefault blog imageDefault blog image

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.

Continue reading
About the author
Carlo Loregian
Solutions Engineer
Your data. Our AI.
Elevate your network security with Darktrace AI