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July 7, 2021

How Cyber-Attacks Take Down Critical Infrastructure | Darktrace

Cyber-attacks can bypass IT/OT security barriers and threaten your organization's infrastructure. Here's how you can stay protected in today's threat landscape.
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
Oakley Cox
Director of Product
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07
Jul 2021

Balancing Operational Continuity and Safety in Critical Infrastructure

The recent high-profile attacks against Colonial Pipeline and JBS Foods highlight that operational technology (OT) — the devices that drive gas flows and food processing, along with essentially all other machine-driven physical processes — does not need to be directly targeted in order to be shut down as the result of a cyber-attack.

Indeed, in the Colonial Pipeline incident, the information technology (IT) systems were reportedly compromised, with operations shut down intentionally out of an abundance of caution, that is, so as to not risk the attack spreading to OT and threatening safety. This highlights that threats to both human and environmental safety, along with uncertainty as to the scope of infection, present risk factors for these sensitive industrial environments.

Continuity through availability and integrity

In most countries, critical infrastructure (CI) — ranging from power grids and pipelines to transportation and health care — must maintain continuous activity. The recent ransomware attack against Colonial Pipeline demonstrates why this is the case, where gas shortages due to the compromise led to dangerous panic buys and long lines at the pumps.

Ensuring continuous operation of critical infrastructure requires safeguarding the availability and integrity of machinery. This means that organizations overseeing critical infrastructure must foresee any possible risks and implement systems, procedures, and technologies that mitigate or remove these risks so as to keep their operations running.

Operational demand versus safety

Alongside this requirement for operational continuity, and often in opposition to it, is the requirement for operational safety. These requirements can be in opposition because operational continuity demands that devices remain up and running at all costs, and operational safety demands that humans and the environment be protected at all costs.

Safety measures in critical infrastructure have improved and become increasingly prioritized over the last 50 years following numerous high-profile incidents, such as the Bhopal chemical disaster, the Texas City refinery explosion, and the Deepwater Horizon oil spill. Appropriate safety precautions could have likely prevented these incidents, but at the expense of operational continuity.

Consequently, administrators of critical infrastructure have to balance the very real threat that an incident may pose to both human life and the environment with the demand to remain operational at all times. More often than not, the final decision regarding what constitutes an acceptable risk is determined by budgets and cost-benefit analyses.

Cyber-attack: A rising risk profile for critical infrastructure

In 2010, the discovery of the Stuxnet malware — which resulted in a nuclear facility in Iran having its centrifuges ruined via compromised programmable logic controllers (PLCs) — demonstrated that critical infrastructure could be targeted by a cyber-attack.

At the time of Stuxnet, critical infrastructure industries used computers designed to ensure operational continuity with little regard for cyber security, as at the time the risk of a cyber-attack seemed either non-existent or vanishingly low. Since then, a number of attacks targeting industrial environments that have emerged on the global threat landscape.

Figure 1: An overview of distinctive methods used in attacks against industrial environments

Classic strains of industrial malware, such as Stuxnet, Triton, and Industroyer, have historically been installed via removable media, such as USB. This is because OT networks are traditionally segregated from the Internet in what is known as an ‘air gap.’ And this remains a prevalent vector of attack, with a study recently finding that cyber-threats installed via USB and other external media doubled in 2021, with 79% of these holding the potential to disrupt OT.

In many ways, operational demands in the subsequent 10 years have made critical infrastructure even more vulnerable. These include the convergence of information technology and operational technology (IT/OT convergence), the adoption of devices in the Industrial Internet of Things (IIoT), and the deprecation of manual back-up systems. This means that OT can be disrupted by cyber-attacks that first target IT systems, rather than having to be installed manually via external media.

At the same time, recent government initiatives — such as the Department of Energy’s 100-day ‘cyber sprint’ to protect electricity operations and President Biden’s Executive Order on Improving the Nation’s Cybersecurity — and regulatory frameworks and directives such as the EU’s NIS directive have either encouraged or mandated that critical infrastructure industries start addressing this new risk.

With the severe and persistent threat that cyber-attacks pose to critical infrastructure, including maritime cybersecurity, and the increasing calls to address the issue, the question remains as to how to best achieve robust cyber defense.

Assessing the risk

To claim administrators of critical infrastructure are ignorant or oblivious to the threat posed by cyber-attacks would be unfair. Many organizations have implemented changes to mitigate or remove the risk either as a result of regulation or their own forward thinking.

However, these projects can take years, even decades. High costs and ever-changing operational demand also mean that these projects may never fully remove the risk.

As a result, many operators may understand the threat of a cyber-attack but not be in a position to do anything about it in the short or medium term. Instead, procedures have to be put in place to minimize risk even if this threatens operational continuity.

For example, a risk assessment may decide it is best to shut down all OT operations in the event of a cyber-attack in order to avoid a major accident. This abundance of caution is forced upon operators, who do not have the ability to immediately confirm the boundaries of a compromise. The prevalence of cyber insurance provides this option with further appeal. Any losses incurred by stopping operations can theoretically be recouped and the risk is therefore transferred.

While the full details of the Colonial Pipeline ransomware incident are still to be determined, the sequence of events outlined below provides a plausible explanation for how a cyber-attack could take down critical infrastructure, even when that cyber-attack does not reach or even target OT systems. Indeed, the CEO of Colonial Pipeline, in a testimony to congress, confirmed “the imperative to isolate and contain the attack to help ensure the malware did not spread to the operational technology network, which controls our pipeline operations, if it had not already.”

Figure 2: A sequence of events which may lead to critical infrastructure being shut down by a cyber-attack, even when that cyber-attack doesn’t directly impact OT networks

The limits of securing IT or OT in isolation

The emergence of OT cyber security solutions in the last five years demonstrates that critical infrastructure industries are trying to find a way to address the risks posed by cyber-attacks. But these solutions have limited scope, as they assume IT and OT are separated and use legacy security techniques such as malware signatures and patch management.

The 2021 SANS ICS Security Summit highlighted how the OT security community suffers from a lack of visibility in knowing and understanding their networks. For many organizations, simply determining whether an unusual incident is an attack or the result of a software error is a challenge.

Given that most OT cyber-attacks actually start in IT networks before pivoting into OT, investing in an IT security solution rather than an OT-specific solution may at first seem like a better business decision. But IT solutions fall short if an attacker successfully pivots into the OT network, or if the attacker is a rogue insider who already has direct access to the OT network. A siloed approach to securing either IT or OT in isolation will thus fall short of the full scope needed to safeguard industrial systems.

It is clear that a mature security posture for critical infrastructure would include security solutions for both IT and OT. Even then, using separate solutions to protect the IT and OT networks is limited, as it presents challenges when defending network boundaries and detecting incidents when an attacker pivots from IT to OT. Under time pressure, a security team does not want changes in visibility, detection, language or interface while trying to determine whether a threat crossed the ‘boundary’ between IT and OT.

Separate solutions can also make detecting an attacker abusing traditional IT attack TTPs within an OT network much harder if the security team is relying on a purely OT solution to defend the OT environment. Examples of this include the abuse of IT remote management tools to affect industrial environments, such as in the suspected cyber-attack at the Florida water facility earlier this year. Cybersecurity for utilities is becoming increasingly important as these sectors face growing cyber threats that can disrupt essential services.

Using AI to minimize cyber risk and maximize cyber safety

In contrast, Darktrace AI is able to defend an entire cyber ecosystem estate, building a ‘pattern of life’ across IT and OT, as well as the points at which they converge. Consequently, cyber security teams can use a single pane of glass to detect and respond to cyber-attacks as they emerge and develop, regardless of where they are in the environment.

Use cases for Darktrace’s Self-Learning AI include containing pre-existing threats to maintain continuous operations. This was seen when Darktrace’s AI detected pre-existing infections and acted autonomously to contain the threat, allowing the operator to leave infected IIoT devices active while waiting for replacements. Darktrace can also thwart ransomware in IT before it can spread into OT, as when Darktrace detected a ransomware attack targeting a supplier for critical infrastructure in North America at its earliest stages.

Darktrace’s unified protection, including visibility and early detection of zero-days, empowers security teams to overcome uncertainty and make a confident decision not to shut down operations. Darktrace has already demonstrated this ability in the wild, and allows organizations to understand normal machine and human behavior in order to enforce this behavior, even in the face of an emerging cyber-attack.

Inside the SOC
Darktrace cyber analysts are world-class experts in threat intelligence, threat hunting and incident response, and provide 24/7 SOC support to thousands of Darktrace customers around the globe. Inside the SOC is exclusively authored by these experts, providing analysis of cyber incidents and threat trends, based on real-world experience in the field.
Written by
Oakley Cox
Director of Product

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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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