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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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December 18, 2025

Why organizations are moving to label-free, behavioral DLP for outbound email

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Why outbound email DLP needs reinventing

In 2025, the global average cost of a data breach fell slightly — but remains substantial at USD 4.44 million (IBM Cost of a Data Breach Report 2025). The headline figure hides a painful reality: many of these breaches stem not from sophisticated hacks, but from simple human error: mis-sent emails, accidental forwarding, or replying with the wrong attachment. Because outbound email is a common channel for sensitive data leaving an organization, the risk posed by everyday mistakes is enormous.

In 2025, 53% of data breaches involved customer PII, making it the most commonly compromised asset (IBM Cost of a Data Breach Report 2025). This makes “protection at the moment of send” essential. A single unintended disclosure can trigger compliance violations, regulatory scrutiny, and erosion of customer trust –consequences that are disproportionate to the marginal human errors that cause them.

Traditional DLP has long attempted to mitigate these impacts, but it relies heavily on perfect labelling and rigid pattern-matching. In reality, data loss rarely presents itself as a neat, well-structured pattern waiting to be caught – it looks like everyday communication, just slightly out of context.

How data loss actually happens

Most data loss comes from frustratingly familiar scenarios. A mistyped name in auto-complete sends sensitive data to the wrong “Alex.” A user forwards a document to a personal Gmail account “just this once.” Someone shares an attachment with a new or unknown correspondent without realizing how sensitive it is.

Traditional, content-centric DLP rarely catches these moments. Labels are missing or wrong. Regexes break the moment the data shifts formats. And static rules can’t interpret the context that actually matters – the sender-recipient relationship, the communication history, or whether this behavior is typical for the user.

It’s the everyday mistakes that hurt the most. The classic example: the Friday 5:58 p.m. mis-send, when auto-complete selects Martin, a former contractor, instead of Marta in Finance.

What traditional DLP approaches offer (and where gaps remain)

Most email DLP today follows two patterns, each useful but incomplete.

  • Policy- and label-centric DLP works when labels are correct — but content is often unlabeled or mislabeled, and maintaining classification adds friction. Gaps appear exactly where users move fastest
  • Rule and signature-based approaches catch known patterns but miss nuance: human error, new workflows, and “unknown unknowns” that don’t match a rule

The takeaway: Protection must combine content + behavior + explainability at send time, without depending on perfect labels.

Your technology primer: The three pillars that make outbound DLP effective

1) Label-free (vs. data classification)

Protects all content, not just what’s labeled. Label-free analysis removes classification overhead and closes gaps from missing or incorrect tags. By evaluating content and context at send time, it also catches misdelivery and other payload-free errors.

  • No labeling burden; no regex/rule maintenance
  • Works when tags are missing, wrong, or stale
  • Detects misdirected sends even when labels look right

2) Behavioral (vs. rules, signatures, threat intelligence)

Understands user behavior, not just static patterns. Behavioral analysis learns what’s normal for each person, surfacing human error and subtle exfiltration that rules can’t. It also incorporates account signals and inbound intel, extending across email and Teams.

  • Flags risk without predefined rules or IOCs
  • Catches misdelivery, unusual contacts, personal forwards, odd timing/volume
  • Blends identity and inbound context across channels

3) Proprietary DSLM (vs. generic LLM)

Optimized for precise, fast, explainable on-send decisions. A DSLM understands email/DLP semantics, avoids generative risks, and stays auditable and privacy-controlled, delivering intelligence reliably without slowing mail flow.

  • Low-latency, on-send enforcement
  • Non-generative for predictable, explainable outcomes
  • Governed model with strong privacy and auditability

The Darktrace approach to DLP

Darktrace / EMAIL – DLP stops misdelivery and sensitive data loss at send time using hold/notify/justify/release actions. It blends behavioral insight with content understanding across 35+ PII categories, protecting both labeled and unlabeled data. Every action is paired with clear explainability: AI narratives show exactly why an email was flagged, supporting analysts and helping end-users learn. Deployment aligns cleanly with existing SOC workflows through mail-flow connectors and optional Microsoft Purview label ingestion, without forcing duplicate policy-building.

Deployment is simple: Microsoft 365 routes outbound mail to Darktrace for real-time, inline decisions without regex or rule-heavy setup.

A buyer’s checklist for DLP solutions

When choosing your DLP solution, you want to be sure that it can deliver precise, explainable protection at the moment it matters – on send – without operational drag.  

To finish, we’ve compiled a handy list of questions you can ask before choosing an outbound DLP solution:

  • Can it operate label free when tags are missing or wrong? 
  • Does it truly learn per user behavior (no shortcuts)? 
  • Is there a domain specific model behind the content understanding (not a generic LLM)? 
  • Does it explain decisions to both analysts and end users? 
  • Will it integrate with your label program and SOC workflows rather than duplicate them? 

For a deep dive into Darktrace’s DLP solution, check out the full solution brief.

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Carlos Gray
Senior Product Marketing Manager, Email

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December 17, 2025

Beyond MFA: Detecting Adversary-in-the-Middle Attacks and Phishing with Darktrace

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What is an Adversary-in-the-middle (AiTM) attack?

Adversary-in-the-Middle (AiTM) attacks are a sophisticated technique often paired with phishing campaigns to steal user credentials. Unlike traditional phishing, which multi-factor authentication (MFA) increasingly mitigates, AiTM attacks leverage reverse proxy servers to intercept authentication tokens and session cookies. This allows attackers to bypass MFA entirely and hijack active sessions, stealthily maintaining access without repeated logins.

This blog examines a real-world incident detected during a Darktrace customer trial, highlighting how Darktrace / EMAILTM and Darktrace / IDENTITYTM identified the emerging compromise in a customer’s email and software-as-a-service (SaaS) environment, tracked its progression, and could have intervened at critical moments to contain the threat had Darktrace’s Autonomous Response capability been enabled.

What does an AiTM attack look like?

Inbound phishing email

Attacks typically begin with a phishing email, often originating from the compromised account of a known contact like a vendor or business partner. These emails will often contain malicious links or attachments leading to fake login pages designed to spoof legitimate login platforms, like Microsoft 365, designed to harvest user credentials.

Proxy-based credential theft and session hijacking

When a user clicks on a malicious link, they are redirected through an attacker-controlled proxy that impersonates legitimate services.  This proxy forwards login requests to Microsoft, making the login page appear legitimate. After the user successfully completes MFA, the attacker captures credentials and session tokens, enabling full account takeover without the need for reauthentication.

Follow-on attacks

Once inside, attackers will typically establish persistence through the creation of email rules or registering OAuth applications. From there, they often act on their objectives, exfiltrating sensitive data and launching additional business email compromise (BEC) campaigns. These campaigns can include fraudulent payment requests to external contacts or internal phishing designed to compromise more accounts and enable lateral movement across the organization.

Darktrace’s detection of an AiTM attack

At the end of September 2025, Darktrace detected one such example of an AiTM attack on the network of a customer trialling Darktrace / EMAIL and Darktrace / IDENTITY.

In this instance, the first indicator of compromise observed by Darktrace was the creation of a malicious email rule on one of the customer’s Office 365 accounts, suggesting the account had likely already been compromised before Darktrace was deployed for the trial.

Darktrace / IDENTITY observed the account creating a new email rule with a randomly generated name, likely to hide its presence from the legitimate account owner. The rule marked all inbound emails as read and deleted them, while ignoring any existing mail rules on the account. This rule was likely intended to conceal any replies to malicious emails the attacker had sent from the legitimate account owner and to facilitate further phishing attempts.

Darktrace’s detection of the anomalous email rule creation.
Figure 1: Darktrace’s detection of the anomalous email rule creation.

Internal and external phishing

Following the creation of the email rule, Darktrace / EMAIL observed a surge of suspicious activity on the user’s account. The account sent emails with subject lines referencing payment information to over 9,000 different external recipients within just one hour. Darktrace also identified that these emails contained a link to an unusual Google Drive endpoint, embedded in the text “download order and invoice”.

Darkrace’s detection of an unusual surge in outbound emails containing suspicious content, shortly following the creation of a new email rule.
Figure 2: Darkrace’s detection of an unusual surge in outbound emails containing suspicious content, shortly following the creation of a new email rule.
Darktrace / EMAIL’s detection of the compromised account sending over 9,000 external phishing emails, containing an unusual Google Drive link.
Figure 3: Darktrace / EMAIL’s detection of the compromised account sending over 9,000 external phishing emails, containing an unusual Google Drive link.

As Darktrace / EMAIL flagged the message with the ‘Compromise Indicators’ tag (Figure 2), it would have been held automatically if the customer had enabled default Data Loss Prevention (DLP) Action Flows in their email environment, preventing any external phishing attempts.

Figure 4: Darktrace / EMAIL’s preview of the email sent by the offending account.
Figure 4: Darktrace / EMAIL’s preview of the email sent by the offending account.

Darktrace analysis revealed that, after clicking the malicious link in the email, recipients would be redirected to a convincing landing page that closely mimicked the customer’s legitimate branding, including authentic imagery and logos, where prompted to download with a PDF named “invoice”.

Figure 5: Download and login prompts presented to recipients after following the malicious email link, shown here in safe view.

After clicking the “Download” button, users would be prompted to enter their company credentials on a page that was likely a credential-harvesting tool, designed to steal corporate login details and enable further compromise of SaaS and email accounts.

Darktrace’s Response

In this case, Darktrace’s Autonomous Response was not fully enabled across the customer’s email or SaaS environments, allowing the compromise to progress,  as observed by Darktrace here.

Despite this, Darktrace / EMAIL’s successful detection of the malicious Google Drive link in the internal phishing emails prompted it to suggest ‘Lock Link’, as a recommended action for the customer’s security team to manually apply. This action would have automatically placed the malicious link behind a warning or screening page blocking users from visiting it.

Autonomous Response suggesting locking the malicious Google Drive link sent in internal phishing emails.
Figure 6: Autonomous Response suggesting locking the malicious Google Drive link sent in internal phishing emails.

Furthermore, if active in the customer’s SaaS environment, Darktrace would likely have been able to mitigate the threat even earlier, at the point of the first unusual activity: the creation of a new email rule. Mitigative actions would have included forcing the user to log out, terminating any active sessions, and disabling the account.

Conclusion

AiTM attacks represent a significant evolution in credential theft techniques, enabling attackers to bypass MFA and hijack active sessions through reverse proxy infrastructure. In the real-world case we explored, Darktrace’s AI-driven detection identified multiple stages of the attack, from anomalous email rule creation to suspicious internal email activity, demonstrating how Autonomous Response could have contained the threat before escalation.

MFA is a critical security measure, but it is no longer a silver bullet. Attackers are increasingly targeting session tokens rather than passwords, exploiting trusted SaaS environments and internal communications to remain undetected. Behavioral AI provides a vital layer of defense by spotting subtle anomalies that traditional tools often miss

Security teams must move beyond static defenses and embrace adaptive, AI-driven solutions that can detect and respond in real time. Regularly review SaaS configurations, enforce conditional access policies, and deploy technologies that understand “normal” behavior to stop attackers before they succeed.

Credit to David Ison (Cyber Analyst), Bertille Pierron (Solutions Engineer), Ryan Traill (Analyst Content Lead)

Appendices

Models

SaaS / Anomalous New Email Rule

Tactic – Technique – Sub-Technique  

Phishing - T1566

Adversary-in-the-Middle - T1557

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About the author
David Ison
Cyber Analyst
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