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February 11, 2025

NIS2 Compliance: Interpreting 'State-of-the-Art' for Organisations

This blog explores key technical factors that define state-of-the-art cybersecurity. Drawing on expertise from our business, academia, and national security standards, outlining five essential criteria.
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
Livia Fries
Public Policy Manager, EMEA
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11
Feb 2025

NIS2 Background

17 October 2024 marked the deadline for European Union (EU) Member States to implement the NIS2 Directive into national law. The Directive aims to enhance the EU’s cybersecurity posture by establishing a high common level of cybersecurity for critical infrastructure and services. It builds on its predecessor, the 2018 NIS Directive, by expanding the number of sectors in scope, enforcing greater reporting requirements and encouraging Member States to ensure regulated organisations adopt ‘state-of-the-art' security measures to protect their networks, OT and IT systems.  

Timeline of NIS2
Figure 1: Timeline of NIS2

The challenge of NIS2 & 'state-of-the-art'

Preamble (51) - "Member States should encourage the use of any innovative technology, including artificial intelligence, the use of which could improve the detection and prevention of cyberattacks, enabling resources to be diverted towards cyberattacks more effectively."
Article 21 - calls on Member States to ensure that essential and important entities “take appropriate and proportionate” cyber security measures, and that they do so by “taking into account the state-of-the-art and, where applicable, relevant European and international standards, as well as the cost of implementation.”

Regulatory expectations and ambiguity of NIS2

While organisations in scope can rely on technical guidance provided by ENISA1 , the EU’s agency for cybersecurity, or individual guidelines provided by Member States or Public-Private Partnerships where they have been published,2 the mention of ‘state-of-the-art' remains up to interpretation in most Member States. The use of the phrase implies that cybersecurity measures must evolve continuously to keep pace with emerging threats and technological advancements without specifying what ‘state-of-the-art’ actually means for a given context and risk.3  

This ambiguity makes it difficult for organisations to determine what constitutes compliance at any given time and could lead to potential inconsistencies in implementation and enforcement. Moreover, the rapid pace of technological change means that what is considered "state-of-the-art" today will become outdated, further complicating compliance efforts.

However, this is not unique to NIS regulation. As EU scholars have noted, while “state-of-the-art" is widely referred to in legal text relating to technology, there is no standardised legal definition of what it actually constitutes.4

Defining state-of-the-art cybersecurity

In this blog, we outline technical considerations for state-of-the-art cybersecurity. We draw from expertise within our own business and in academia as well as guidelines and security standards set by national agencies, such as Germany’s Federal Office for Information Security (BSI) or Spain’s National Security Framework (ENS), to put forward five criteria to define state-of-the-art cybersecurity.

The five core criteria include:

  • Continuous monitoring
  • Incident correlation
  • Detection of anomalous activity
  • Autonomous response
  • Proactive cyber resilience

These principles build on long-standing security considerations, such as business continuity, vulnerability management and basic security hygiene practices.  

Although these considerations are written in the context of the NIS2 Directive, they are likely to also be relevant for other jurisdictions. We hope these criteria help organisations understand how to best meet their responsibilities under the NIS2 Directive and assist Competent Authorities in defining compliance expectations for the organisations they regulate.  

Ultimately, adopting state-of-the-art cyber defences is crucial for ensuring that organisations are equipped with the best tools to combat new and fast-growing threats. Leading technical authorities, such as the UK National Cyber Security Centre (NCSC), recognise that adoption of AI-powered cyber defences will offset the increased volume and impact of AI on cyber threats.5

State of the art cybersecurity in the context of NIS2

1. Continuous monitoring

Continuous monitoring is required to protect an increasingly complex attack surface from attackers.

First, organisations' attack surfaces have expanded following the widespread adoption of hybrid or cloud infrastructures and the increased adoption of connected Internet of Things (IoT) devices.6 This exponential growth creates a complex digital environment for organisations, making it difficult for security teams to track all internet-facing assets and identify potential vulnerabilities.

Second, with the significant increase in the speed and sophistication of cyber-attacks, organisations face a greater need to detect security threats and non-compliance issues in real-time.  

Continuous monitoring, defined by the U.S. National Institute of Standards and Technology (NIST) as the ability to maintain “ongoing awareness of information security, vulnerabilities, and threats to support organizational risk management decisions,”7 has therefore become a cornerstone of an effective cybersecurity strategy. By implementing continuous monitoring, organisations can ensure a real-time understanding of their attack surface and that new external assets are promptly accounted for. For instance, Spain’s technical guidelines for regulation, as set forth by the National Security Framework (Royal Decree 311/2022), highlight the importance of adopting continuous monitoring to detect anomalous activities or behaviours and to ensure timely responses to potential threats (article 10).8  

This can be achieved through the following means:  

All assets that form part of an organisation's estate, both known and unknown, must be identified and continuously monitored for current and emerging risks. Germany’s BSI mandates the continuous monitoring of all protocol and logging data in real-time (requirement #110).9 This should be conducted alongside any regular scans to detect unknown devices or cases of shadow IT, or the use of unauthorised or unmanaged applications and devices within an organisation, which can expose internet-facing assets to unmonitored risks. Continuous monitoring can therefore help identify potential risks and high-impact vulnerabilities within an organisation's digital estate and eliminate potential gaps and blind spots.

Organisations looking to implement more efficient continuous monitoring strategies may turn to automation, but, as the BSI notes, it is important for responsible parties to be immediately warned if an alert is raised (reference 110).10 Following the BSI’s recommendations, the alert must be examined and, if necessary, contained within a short period of time corresponding with the analysis of the risk at hand.

Finally, risk scoring and vulnerability mapping are also essential parts of this process. Continuous monitoring helps identify potential risks and significant vulnerabilities within an organisation's digital assets, fostering a dynamic understanding of risk. By doing so, risk scoring and vulnerability mapping allows organisations to prioritise the risks associated with their most critically exposed assets.

2. Correlation of incidents across your entire environment

Viewing and correlating incident alerts when working with different platforms and tools poses significant challenges to SecOps teams. Security professionals often struggle to cross-reference alerts efficiently, which can lead to potential delays in identifying and responding to threats. The complexity of managing multiple sources of information can overwhelm teams, making it difficult to maintain a cohesive understanding of the security landscape.

This fragmentation underscores the need for a centralised approach that provides a "single pane of glass" view of all cybersecurity alerts. These systems streamline the process of monitoring and responding to incidents, enabling security teams to act more swiftly and effectively. By consolidating alerts into a unified interface, organisations can enhance their ability to detect and mitigate threats, ultimately improving their overall security posture.  

To achieve consolidation, organisations should consider the role automation can play when reviewing and correlating incidents. This is reflected in Spain’s technical guidelines for national security regulations regarding the requirements for the “recording of activity” (reinforcement R5).12 Specifically, the guidelines state that:  

"The system shall implement tools to analyses and review system activity and audit information, in search of possible or actual security compromises. An automatic system for collection of records, correlation of events and automatic response to them shall be available”.13  

Similarly, the German guidelines stress that automated central analysis is essential not only for recording all protocol and logging data generated within the system environment but also to ensure that the data is correlated to ensure that security-relevant processes are visible (article 115).14

Correlating disparate incidents and alerts is especially important when considering the increased connectivity between IT and OT environments driven by business and functional requirements. Indeed, organisations that believe they have air-gapped systems are now becoming aware of points of IT/OT convergence within their systems. It is therefore crucial for organisations managing both IT and OT environments to be able to visualise and secure devices across all IT and OT protocols in real-time to identify potential spillovers.  

By consolidating data into a centralised system, organisations can achieve a more resilient posture. This approach exposes and eliminates gaps between people, processes, and technology before they can be exploited by malicious actors. As seen in the German and Spanish guidelines, a unified view of security alerts not only enhances the efficacy of threat detection and response but also ensures comprehensive visibility and control over the organisation's cybersecurity posture.

3. Detection of anomalous activity  

Recent research highlights the emergence of a "new normal" in cybersecurity, marked by an increase in zero-day vulnerabilities. Indeed, for the first time since sharing their annual list, the Five Eyes intelligence alliance reported that in 2023, the majority of the most routinely exploited vulnerabilities were initially exploited as zero-days.15  

To effectively combat these advanced threats, policymakers, industry and academic stakeholders alike recognise the importance of anomaly-based techniques to detect both known and unknown attacks.

As AI-enabled threats become more prevalent,16 traditional cybersecurity methods that depend on lists of "known bads" are proving inadequate against rapidly evolving and sophisticated attacks. These legacy approaches are limited because they can only identify threats that have been previously encountered and cataloged. However, cybercriminals are constantly developing new, never-before-seen threats, such as signatureless ransomware or living off the land techniques, which can easily bypass these outdated defences.

The importance of anomaly detection in cybersecurity can be found in Spain’s technical guidelines, which states that “tools shall be available to automate the prevention and response process by detecting and identifying anomalies17” (reinforcement R4 prevention and automatic response to "incident management”).  

Similarly, the UK NCSC’s Cyber Assessment Framework (CAF) highlights how anomaly-based detection systems are capable of detecting threats that “evade standard signature-based security solutions” (Principle C2 - Proactive Security Event Discovery18). The CAF’s C2 principle further outlines:  

“The science of anomaly detection, which goes beyond using pre-defined or prescriptive pattern matching, is a challenging area. Capabilities like machine learning are increasingly being shown to have applicability and potential in the field of intrusion detection.”19

By leveraging machine learning and multi-layered AI techniques, organisations can move away from static rules and signatures, adopting a more behavioural approach to identifying and containing risks. This shift not only enhances the detection of emerging threats but also provides a more robust defence mechanism.

A key component of this strategy is behavioral zero trust, which focuses on identifying unauthorized and out-of-character attempts by users, devices, or systems. Implementing a robust procedure to verify each user and issuing the minimum required access rights based on their role and established patterns of activity is essential. Organisations should therefore be encouraged to follow a robust procedure to verify each user and issue the minimum required access rights based on their role and expected or established patterns of activity. By doing so, organisations can stay ahead of emerging threats and embrace a more dynamic and resilient cybersecurity strategy.  

4. Autonomous response

The speed at which cyber-attacks occur means that defenders must be equipped with tools that match the sophistication and agility of those used by attackers. Autonomous response tools are thus essential for modern cyber defence, as they enable organisations to respond to both known and novel threats in real time.  

These tools leverage a deep contextual and behavioral understanding of the organisation to take precise actions, effectively containing threats without disrupting business operations.

To avoid unnecessary business disruptions and maintain robust security, especially in more sensitive networks such as OT environments, it is crucial for organisations to determine the appropriate response depending on their environment. This can range from taking autonomous and native actions, such as isolating or blocking devices, or integrating their autonomous response tool with firewalls or other security tools to taking customized actions.  

Autonomous response solutions should also use a contextual understanding of the business environment to make informed decisions, allowing them to contain threats swiftly and accurately. This means that even as cyber-attacks evolve and become more sophisticated, organisations can maintain continuous protection without compromising operational efficiency.  

Indeed, research into the adoption of autonomous cyber defences points to the importance of implementing “organisation-specific" and “context-informed” approaches.20  To decide the appropriate level of autonomy for each network action, it is argued, it is essential to use evidence-based risk prioritisation that is customised to the specific operations, assets, and data of individual enterprises.21

By adopting autonomous response solutions, organisations can ensure their defences are as dynamic and effective as the threats they face, significantly enhancing their overall security posture.

5. Proactive cyber resilience  

Adopting a proactive approach to cybersecurity is crucial for organisations aiming to safeguard their operations and reputation. By hardening their defences enough so attackers are unable to target them effectively, organisations can save significant time and money. This proactive stance helps reduce business disruption, reputational damage, and the need for lengthy, resource-intensive incident responses.

Proactive cybersecurity incorporates many of the strategies outlined above. This can be seen in a recent survey of information technology practitioners, which outlines four components of a proactive cybersecurity culture: (1) visibility of corporate assets, (2) leveraging intelligent and modern technology, (3) adopting consistent and comprehensive training methods and (4) implementing risk response procedures.22 To this, we may also add continuous monitoring which allows organisations to understand the most vulnerable and high-value paths across their architectures, allowing them to secure their critical assets more effectively.  

Alongside these components, a proactive cyber strategy should be based on a combined business context and knowledge, ensuring that security measures are aligned with the organisation's specific needs and priorities.  

This proactive approach to cyber resilience is reflected in Spain’s technical guidance (article 8.2): “Prevention measures, which may incorporate components geared towards deterrence or reduction of the exposure surface, should eliminate or reduce the likelihood of threats materializing.”23 It can also be found in the NCSC’s CAF, which outlines how organisations can achieve “proactive attack discovery” (see Principle C2).24 Likewise, Belgium’s NIS2 transposition guidelines mandate the use of preventive measures to ensure the continued availability of services in the event of exceptional network failures (article 30).25  

Ultimately, a proactive approach to cybersecurity not only enhances protection but also lowers regulatory risk and supports the overall resilience and stability of the organisation.

Looking forward

The NIS2 Directive marked a significant regulatory milestone in strengthening cybersecurity across the EU.26 Given the impact of emerging technologies, such as AI, on cybersecurity, it is to see that Member States are encouraged to promote the adoption of ‘state-of-the-art' cybersecurity across regulated entities.  

In this blog, we have sought to translate what state-of-the-art cybersecurity may look like for organisations looking to enhance their cybersecurity posture. To do so, we have built on existing cybersecurity guidance, research and our own experience as an AI-cybersecurity company to outline five criteria: continuous monitoring, incident correlation, detection of anomalous activity, autonomous response, and proactive cyber resilience.

By embracing these principles and evolving cybersecurity practices in line with the state-of-the-art, organisations can comply with the NIS2 Directive while building a resilient cybersecurity posture capable of withstanding evolutions in the cyber threat landscape. Looking forward, it will be interesting to see how other jurisdictions embrace new technologies, such as AI, in solving the cybersecurity problem.

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References

[1] https://www.enisa.europa.eu/publications/implementation-guidance-on-nis-2-security-measures

[2] https://www.teletrust.de/fileadmin/user_upload/2023-05_TeleTrusT_Guideline_State_of_the_art_in_IT_security_EN.pdf

[3] https://kpmg.com/uk/en/home/insights/2024/04/what-does-nis2-mean-for-energy-businesses.html

[4] https://orbilu.uni.lu/bitstream/10993/50878/1/SCHMITZ_IFIP_workshop_sota_author-pre-print.pdf

[5]https://www.ncsc.gov.uk/report/impact-of-ai-on-cyber-threat

[6] https://www.sciencedirect.com/science/article/pii/S2949715923000793

[7] https://csrc.nist.gov/glossary/term/information_security_continuous_monitoring

[8] https://ens.ccn.cni.es/es/docman/documentos-publicos/39-boe-a-2022-7191-national-security-framework-ens/file

[9] https://www.bsi.bund.de/SharedDocs/Downloads/DE/BSI/KRITIS/Konkretisierung_Anforderungen_Massnahmen_KRITIS.html

[10] https://www.bsi.bund.de/SharedDocs/Downloads/DE/BSI/KRITIS/Konkretisierung_Anforderungen_Massnahmen_KRITIS.html

[12] https://ens.ccn.cni.es/es/docman/documentos-publicos/39-boe-a-2022-7191-national-security-framework-ens/file

[13] https://ens.ccn.cni.es/es/docman/documentos-publicos/39-boe-a-2022-7191-national-security-framework-ens/file

[14] https://www.bsi.bund.de/SharedDocs/Downloads/DE/BSI/KRITIS/Konkretisierung_Anforderungen_Massnahmen_KRITIS.html

[15] https://therecord.media/surge-zero-day-exploits-five-eyes-report

[16] https://www.ncsc.gov.uk/report/impact-of-ai-on-cyber-threat

[17] https://ens.ccn.cni.es/es/docman/documentos-publicos/39-boe-a-2022-7191-national-security-framework-ens/file

[18] https://www.ncsc.gov.uk/collection/cyber-assessment-framework/caf-objective-c-detecting-cyber-security-events/principle-c2-proactive-security-event-discovery

[19] https://www.ncsc.gov.uk/collection/cyber-assessment-framework/caf-objective-c-detecting-cyber-security-events/principle-c2-proactive-security-event-discovery

[20] https://cetas.turing.ac.uk/publications/autonomous-cyber-defence-autonomous-agents

[21] https://cetas.turing.ac.uk/publications/autonomous-cyber-defence-autonomous-agents

[22] https://www.researchgate.net/publication/376170443_Cultivating_Proactive_Cybersecurity_Culture_among_IT_Professional_to_Combat_Evolving_Threats

[23] https://ens.ccn.cni.es/es/docman/documentos-publicos/39-boe-a-2022-7191-national-security-framework-ens/file

[24] https://www.ncsc.gov.uk/collection/cyber-assessment-framework/caf-objective-c-detecting-cyber-security-events/principle-c2-proactive-security-event-discovery

[25] https://www.ejustice.just.fgov.be/mopdf/2024/05/17_1.pdf#page=49

[26] ENISA, NIS Directive 2

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
Livia Fries
Public Policy Manager, EMEA

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August 7, 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.

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.

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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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