ブログ
/
/
May 12, 2021

How AI Protects Critical Infrastructure From Ransomware

Explore the role of AI in safeguarding critical infrastructure from ransomware, as revealed by Darktrace's latest insights.
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
David Masson
VP, Field CISO
Default blog imageDefault blog imageDefault blog imageDefault blog imageDefault blog imageDefault blog image
12
May 2021

Modern Threats to OT Environments

At the 2021 RSA cyber security conference, US Secretary of Homeland Security Alejandro Mayorkas made an era-defining statement regarding the cyber security landscape: “Let me be clear: ransomware now poses a national security threat.”

Last weekend, Mayorkas’ words rang true. A ransomware attack on the Colonial Pipeline – responsible for nearly half of the US East Coast’s diesel, gasoline, and jet fuel – resulted in the shutdown of a critical fuel network supplying a number of Eastern states.

The fallout from the attack demonstrated how widespread and damaging the consequences of ransomware can be. Against critical infrastructure and utilities, cyber-attacks have the potential to disrupt supplies, harm the environment, and even threaten human lives.

Though full details remain to be confirmed, the attack is reported to have been conducted by an affiliate of the cyber-criminal group called DarkSide, and likely leveraged common remote desktop tools. Remote access has been enabled as an exploitable vulnerability within critical infrastructure by the shift to remote work that many organizations made last year, including those with Industrial Control Systems (ICS) and Operational Technology (OT).

The rise of industrial ransomware

Ransomware against industrial environments is on the rise, with a reported 500% increase since 2018. Oftentimes, these threats leverage the convergence of IT and OT systems, first targeting IT before pivoting to OT. This was seen with the EKANS ransomware that included ICS processes in its ‘kill list’, as well as the Cring ransomware that compromised ICS after first exploiting a vulnerability in a virtual private network (VPN).

It remains to be seen whether the initial attack vector in the Colonial Pipeline compromise exploited a technical vulnerability, compromised credentials, or a targeted spear phishing campaign. It has been reported that the attack first impacted IT systems, and that Colonial then shut down OT operations as a safety precaution. Colonial confirms that the ransomware “temporarily halted all pipeline operations and affected some of our IT systems,” showing that, ultimately, both OT and IT were affected. This is a great example of how many OT systems depend on IT, such that an IT cyber-attack has the ability to take down OT and ICS processes.

In addition to locking down systems, the threat actors also stole 100GB of sensitive data from Colonial. This kind of double extortion attack — in which data is exfiltrated before files are encrypted — has unfortunately become the norm rather than the exception, with over 70% of ransomware attacks involving exfiltration. Some ransomware gangs have even announced that they are dropping encryption altogether in favor of data theft and extortion methods.

Earlier this year, Darktrace defended against a double extortion ransomware attack waged against a critical infrastructure organization, which also leveraged common remote access tools. This blog will outline the threat find in depth, showing how Darktrace’s self-learning AI responded autonomously to an attack strikingly similar to the Colonial Pipeline incident.

Darktrace threat find

Ransomware against electric utilities equipment supplier

In an attack against a North American equipment supplier for electrical utilities earlier this year, Darktrace/OT demonstrated its ability to protect critical infrastructure against double extortion ransomware that targeted organizations with ICS and OT.

The ransomware attack initially targeted IT systems, and, thanks to self-learning Cyber AI, was stopped before it could spill over into OT and disrupt operations.

The attacker first compromised an internal server in order to exfiltrate data and deploy ransomware over the course of 12 hours. The short amount of time between initial compromise and deployment is unusual, as ransomware threat actors often wait several days to spread stealthily as far across the cyber ecosystem as possible before striking.

Figure 1: A timeline of the attack

How did the attack bypass the rest of the security stack?

The attacker leveraged ‘Living off the Land’ techniques to blend into the business’ normal ‘patterns of life’, using a compromised admin credential and a remote management tool approved by the organization, in its attempts to remain undetected.

Darktrace commonly sees the abuse of legitimate remote management software in attackers’ arsenal of techniques, tactics, and procedures (TTPs). Remote access is also becoming an increasingly common vector of attack in ICS attacks in particular. For example, in the cyber-incident at the Florida water treatment facility last February, attackers exploited a remote management tool in attempts to manipulate the treatment process.

The specific strain of ransomware deployed by this attacker also successfully evaded detection by anti-virus by using a unique file extension when encrypting files. These forms of ‘signatureless’ ransomware easily slip past legacy approaches to security that rely on rules, signatures, threat feeds, and lists of documented Common Vulnerabilities and Exposures (CVEs), as these are methods that can only detect previously documented threats.

The only way to detect never-before-seen threats like signatureless ransomware is for a technology to find anomalous behavior, rather than rely on lists of ‘known bads’. This can be achieved with self-learning technology, which spots even the most subtle deviations from the normal ‘patterns of life’ for all devices, users, and all the connections between them.

Darktrace insights

Initial compromise and establishing foothold

Despite the abuse of a legitimate tool and the absence of known signatures, Darktrace/OT was able to use a holistic understanding of normal activity to detect the malicious activity at multiple points in the attack lifecycle.

The first clear sign of an emerging threat that was alerted by Darktrace was the unusual use of a privileged credential. The device also served an unusual remote desktop protocol (RDP) connection from a Veeam server shortly before the incident, indicating that the attacker may have moved laterally from elsewhere in the network.

Three minutes later, the device initiated a remote management session which lasted 21 hours. This allowed the attacker to move throughout the broader cyber ecosystem while remaining undetected by traditional defences. Darktrace, however, was able to detect unusual remote management usage as another early warning indicative of an attack.

Double threat part one: Data exfiltration

One hour after the initial compromise, Darktrace detected unusual volumes of data being sent to a 100% rare cloud storage solution, pCloud. The outbound data was encrypted using SSL, but Darktrace created multiple alerts relating to large internal downloads and external uploads that were a significant deviation from the device’s normal ‘pattern of life’.

The device continued to exfiltrate data for nine hours. Analysis of the files downloaded by the device, which were transferred using the unencrypted SMB protocol, suggests that they were sensitive in nature. Fortunately, Darktrace was able to pinpoint the specific files that were exfiltrated so that the customer could immediately evaluate the potential implications of the compromise.

Double threat part two: File encryption

A short time later, at 01:49 local time, the compromised device began encrypting files in a SharePoint back-up share drive. Over the next three and a half hours, the device encrypted over 13,000 files on at least 20 SMB shares. In total, Darktrace produced 23 alerts for the device in question, which amounted to 48% of all the alerts produced in the corresponding 24-hour period.

Darktrace’s Cyber AI Analyst then automatically launched an investigation, identifying the internal data transfers and the file encryption over SMB. From this, it was able to present incident reports that connected the dots among these disparate anomalies, piecing them together into a coherent security narrative. This put the security team in a position to immediately take remediating action.

If the customer had been using Darktrace’s autonomous response technology, there is no doubt the activity would have been halted before significant volumes of data could have been exfiltrated or files encrypted. Fortunately, after seeing both the alerts and Cyber AI Analyst reports, the customer was able to use Darktrace’s ‘Ask the Expert’ (ATE) service for incident response to mitigate the impact of the attack and assist with disaster recovery.

Figure 2: AI Analyst Incident reporting an unusual reprogram command using the MODBUS protocol. The incident includes a plain English summary, relevant technical information, and the investigation process used by the AI.  

Detecting the threat before it could disrupt critical infrastructure

The targeted supplier was overseeing OT and had close ties to critical infrastructure. By facilitating the early-stage response, Darktrace prevented the ransomware from spreading further onto the factory floor. Crucially, Darktrace also minimized operational disruption, helping to avoid the domino effect which the attack could have had, affecting not only the supplier itself, but also the electric utilities that this supplier supports.

As both the recent Colonial Pipeline incident and the above threat find reveal, ransomware is a pressing concern for organizations overseeing industrial operations across all forms of critical infrastructure, from pipelines to the power grid and its suppliers. With self-learning AI, these attack vectors can be dealt with before the damage is done through real-time threat detection, autonomous investigations, and — if activated — targeted machine-speed response.

Looking forward: Using Self-Learning AI to protect critical infrastructure across the board

In late April, the Biden administration announced an ambitious effort to “safeguard US critical infrastructure from persistent and sophisticated threats.” The Department of Energy’s (DOE) 100-day plan specifically seeks technologies “that will provide cyber visibility, detection, and response capabilities for industrial control systems of electric utilities.”

The Biden administration’s cyber sprint clearly calls for a technology that protects critical energy infrastructure, rather than merely best practice measures and regulations. As seen in the above threat find, Darktrace AI is a powerful technology that leverages unsupervised machine learning to autonomously safeguard critical infrastructure and its suppliers with machine speed and precision.

Darktrace enhances detection, mitigation, and forensic capabilities to detect  sophisticated and novel attacks, along with insider threats and pre-existing infections, using Self-Learning Cyber AI, without rules, signatures, or lists of CVEs. Incident investigations provided in real time by Cyber AI Analyst jumpstart remediation with actionable insights, containing emerging attacks at their early stages, before they escalate into crisis.

Enable near real-time situational awareness and response capabilities

Darktrace immediately understands, identifies, and investigates all anomalous activity in ICS/OT networks, whether human or machine driven. Additionally, Darktrace actions targeted response where appropriate to neutralize threats, either actively or in human confirmation mode. Because Self-learning AI adapts alongside evolutions in the ecosystem, organizations benefit from real-time awareness with no tuning or human input necessary

Deploy technologies to increase visibility of threats in ICS and OT systems

Darktrace contextualizes security events, adapts to novel techniques, and translates findings into a security narrative that can be actioned by humans in minutes. Delivering a unified view across IT and OT systems.

Darktrace detects, investigates, and responds to threats at higher Purdue levels and in IT systems before they ‘spill over’ into OT. ‘Plug and play’ deployment seamlessly integrates with technological architecture, presenting 3D network topology with granular visibility into all users, devices, and subnets.

Darktrace's asset identification continuously catalogues all ICS/OT devices and identifies and investigates all threatening activity indicative of emerging attacks – be it ICS ransomware, APTs, zero-day exploits, insider threats, pre-existing infections, DDoS, crypto-mining, misconfigurations, or never-before-seen attacks.

Thanks to Darktrace analyst Oakley Cox for his insights on the above threat find.

Darktrace model detections:

  • Initial compromise:
  • User / New Admin Credential on Client
  • Data exfiltration:
  • Anomalous Connection / Uncommon 1 GiB Outbound
  • Anomalous Connection / Low and Slow Exfiltration
  • Device / Anomalous SMB Followed by Multiple Model Breaches
  • Anomalous Connection / Download and Upload
  • File encryption:
  • Compromise / Ransomware / Suspicious SMB Activity
  • Anomalous Connection / SMB Enumeration
  • Device / Anomalous RDP Followed by Multiple Model Breaches
  • Anomalous File / Internal / Additional Extension Appended to SMB File
  • Anomalous Connection / Sustained MIME Type Conversion
  • Anomalous Connection / Suspicious Read Write Ratio
  • Device / Multiple Lateral Movement Model Breaches

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
David Masson
VP, Field CISO

More in this series

No items found.

Blog

/

Email

/

December 18, 2025

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

Default blog imageDefault blog image

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.

[related-resource]

Continue reading
About the author
Carlos Gray
Senior Product Marketing Manager, Email

Blog

/

Email

/

December 17, 2025

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

Default blog imageDefault blog image

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

Continue reading
About the author
あなたのデータ × DarktraceのAI
唯一無二のDarktrace AIで、ネットワークセキュリティを次の次元へ