How Darktrace won an email security trial by learning the business, not the breach
Discover how Darktrace identified a sophisticated business email compromise (BEC) attack to successfully acquire a prospective customer in a trial alongside two other email security vendors. This case demonstrates the clear differentiator of true unsupervised machine learning applied to the right use cases, compared to miscellaneous vendor hype around AI.
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
Carlos Gray
Senior Product Marketing Manager, Email
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02
Oct 2024
Recently, Darktrace ran a customer trial of our email security product for a leading European infrastructure operator looking to upgrade its email protection.
During this prospective customer trial, Darktrace encountered several security incidents that penetrated existing security layers. Two of these incidents were Business Email Compromise (BEC) attacks, which we’re going to take a closer look at here.
Darktrace was deployed for a trial at the same time as two other email security vendors, who were also being evaluated by the prospective customer. Darktrace’s superior detection of threats in this trial laid the groundwork for the respective company to choose our product.
Let’s dig into some of the elements of this Darktrace tech win and how they came to light during this trial.
Why truly intelligent AI starts learning from scratch
Darktrace’s detection capabilities are powered by true unsupervised machine learning, which detects anomalous activity from its ever-evolving understanding of normal for every unique environment. Consequently, it learns every business from the beginning, training on an organization’s data to understand normal for its users, devices, assets and the millions of connections between them.
This learning period takes around a week, during which the AI hones its understanding of the business to a precise degree. At this stage, the system may produce some noise or lack precision, but this is a testament to our unsupervised machine learning. Unlike solutions that promise faster results by relying on preset assumptions, our AI takes the necessary time to learn from scratch, ensuring a deeper understanding and increasingly accurate detection over time.
Real threats detected by Darktrace
Attack 1: Supply chain attack
BEC and supply chain attacks are notoriously difficult to detect, as they take advantage of established, trusted senders.
This attack came from a legitimate server via a known supplier with which the prospective customer had active and ongoing communication. Using the compromised account, the attacker didn’t just send out randomized spam, they crafted four sophisticated social engineering emails with the aim of soliciting users to click on a link – directly tapping into existing conversations. Darktrace / EMAIL was configured in passive mode during this trial; it would otherwise have held the emails before they arrived in the inbox. Luckily in this instance, one user reported the email to the CISO before any other users clicked the link. Upon investigation, the link contained timed ransomware detonation.
Darktrace was the only vendor that caught any of these four emails. Our unique behavioral AI approach enables Darktrace / EMAIL to protect customers from even the most sophisticated attacks that abuse prior trust and relationships.
How did Darktrace catch this attack that other vendors missed?
With traditional email security, security teams have been obliged to allow entire organizations to eliminate false positives – on the premise that it’s easier to make a broad decision based on an entire known domain and assume that potential risk of a supply chain attack.
By contrast, Darktrace adopts a zero trust mentality, analyzing every email to understand whether communication that has previously been safe remains safe. That’s why Darktrace is uniquely positioned to detect BEC, based on its deep learning of internal and external users. Because it creates individual profiles for every account, group and business composed of multiple signals, it can detect deviations in their communication patterns based on the context and content of each message. We think of this as the ‘self-learning’ vs ‘learning the breach’ differentiator.
Fig 1: Darktrace analysis of one of four malicious emails sent by the trusted supplier. It gives it an anomaly score of 100, despite it being from a known correspondent with a known domain relationship and moderate mailing history.
If set in autonomous mode where it can apply actions, Darktrace / EMAIL would have quarantined all four emails. Using machine learning indicators such as ‘Inducement Shift’ and ‘General Behavioral Anomaly’, it deemed the four emails ‘Out of Character’. It also identified the link as highly likely to be phishing, based purely on its context. These indicators are critical because the link itself belonged to a widely used legitimate domain, leveraging their established internet reputation to appear safe.
Around an hour later the supplier regained control of the account and sent a legitimate email alerting a wide distribution list to the phishing emails sent. Darktrace was able to discern the previously sent malicious emails from the current legitimate emails and allowed these emails through. Compared to other vendors that have a static understanding of malicious which needs to be updated (in cases like this, once a supplier is de-compromised), Darktrace’s deep understanding of external entities enables further nuance and precision in determining good from bad.
Fig 2: Darktrace let through four emails (subject line: Virus E-Mail) from the supplier once they had regained control of the compromised account, with a limited anomaly score despite having held the previous malicious emails. If any actions had been taken a red icon would show on the right-hand side – in this instance Darktrace did not take action and let the emails through.
Attack 2: Microsoft 365 account takeover
As part of building behavioral profiles of every email user, Darktrace analyzes their wider account activity. Account activity, such as unusual login patterns and administrative activity, is a key variable to detect account compromise before malicious activity occurs, but it also feeds into Darktrace’s understanding of which emails should belong in every user’s inbox.
When the customer experienced an account compromise on day two of the trial, Darktrace began an investigation and was able to provide the full breakdown and scope of the incident.
The account was compromised via an email, which Darktrace would have blocked if it had been deployed autonomously at the time. Once the account had been compromised, detection details included:
Unusual Login and Account Update
Multiple Unusual External Sources for SaaS Credential
Unusual Activity Block
Login From Rare Endpoint While User is Active
Fig 3: Darktrace flagged the following indicators of compromise that deviated from normal behavior for the user in question, signaling an account takeover
With Darktrace / EMAIL, every user is analyzed for behavioral signals including authentication and configuration activity. Here the unusual login, credential input and rare endpoint were all clear signals a compromised account, contextualized against what is normal for that employee. Because Darktrace isn’t looking at email security merely from the perspective of the inbox. It constantly reevaluates the identity of each individual, group and organization (as defined by their behavioral signals), to determine precisely what belongs in the inbox and what doesn’t.
In this instance, Darktrace / EMAIL would have blocked the incident were it not deployed in passive mode. In the initial intrusion it would have blocked the compromising email. And once the account was compromised, it would have taken direct blocking actions on the account based on the anomalous activity it detected, providing an extra layer of defense beyond the inbox.
Account takeover protection is always part of Darktrace / EMAIL, which can be extended to fully cover Microsoft 365 SaaS with Darktrace / IDENTITY. By bringing SaaS activity into scope, security teams also benefit from an extended set of use cases including compliance and resource management.
“Darktrace was the only AI vendor that showed learning,” – CISO, Trial Customer
Throughout this trial, Darktrace evolved its understanding of the trial customer’s business and its email users. It identified attacks that other vendors did not, while allowing safe emails through. Furthermore, the CISO explicitly cited Darktrace as the only technology that demonstrated autonomous learning. As well as catching threats that other vendors did not, the CISO saw maturity areas such as how Darktrace dealt with non-productive mail and business-as-usual emails, without any user input. Because of the nature of unsupervised ML, Darktrace’s learning of right and wrong will never be static or complete – it will continue to revise its understanding and adapt to the changing business and communications landscape.
This case study highlights a key tenet of Darktrace’s philosophy – that a rules and tuning-based approach will always be one step behind. Delivering benign emails while holding back malicious emails from the same domain demonstrates that safety is not defined in a straight line, or by historical precedent. Only by analyzing every email in-depth for its content and context can you guarantee that it belongs.
While other solutions are making efforts to improve a static approach with AI, Darktrace’s AI remains truly unsupervised so it is dynamic enough to catch the most agile and evolving threats. This is what allows us to protect our customers by plugging a vital gap in their security stack that ensures they can meet the challenges of tomorrow's email attacks.
Interested in learning more about Darktrace / EMAIL? Check out our product hub.
Discover the most advanced cloud-native AI email security solution to protect your domain and brand while preventing phishing, novel social engineering, business email compromise, account takeover, and data loss.
Gain up to 13 days of earlier threat detection and maximize ROI on your current email security
Experience 20-25% more threat blocking power with Darktrace / EMAIL
Stop the 58% of threats bypassing traditional email security
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.
Darktrace / EMAIL Expands Behavioral Defense Across Email and Collaboration Workflows
New capabilities help employees understand suspicious content, give administrators more control over sensitive data, and show security teams where risky workflows sit across the organization.
Journey of a Threat: How Multi-Layered AI Works in Darktrace / EMAIL
Follow a malicious email as it moves through Darktrace / EMAIL’s multi-layered AI system, from raw data to final decision. Each layer works together to detect threats, understand intent, and take autonomous action.
Hiding in Plain Sight: Uncovering a Multi-Stage Ransomware Attack Through Behavioral Detection
Why ransomware has changed
Ransomware attacks have continued to increase globally, with 698 incidents reported in May 2026, representing a 48% rise compared to 472 incidents in May 2025 [1]. At the same time, the ransomware landscape is evolving. Several major ransomware groups, including LockBit [2], have been disrupted by successful joint law enforcement operations, resulting in a shift away from a small number of dominant actors towards a more fragmented and distributed ecosystem. This is increasingly composed of smaller groups who play a specialized role in the attack, such as initial access brokers, affiliates or developers.
As a result, ransomware tactics, techniques, and procedures (TTPs) are becoming more diverse and less predictable. On top of this, adversaries are leveraging native tools and legitimate penetration testing frameworks to evade detection. Anomaly-based detection is therefore critical to identify pre-ransomware activity, rather than relying on signatures associated with a handful of well-known ransomware groups.
As these attacks often unfold over several days, there is a critical window for defenders to act. In this context, behavioral-based detection plays a vital role in identifying suspicious pre-ransomware activity, and enabling early intervention before encryption or exfiltration occurs.
Inside a modern ransomware intrusion
In early 2026, Darktrace detected activity within a customer’s environment related to a multi-stage ransomware intrusion from the initial compromise. This activity does not appear to be attributable to a specific ransomware group, and no known ransomware payload was observed until the final stage.
The attack aligns with a broader industry trend in which compromised virtual private network (VPN) credentials are used as an entry point, followed by rapid internal reconnaissance and lateral movement using legitimate administrative tools. This growing preference for native tools and legitimate frameworks in cyber-attacks illustrates that it is increasingly unreliable to depend solely on traditional indicators of compromise such as known malware signatures or exploit detection.
The intrusion also involved the use of Sliver, an open-source adversary emulation framework, which is increasingly observed in real-world attacks. Originally designed for penetration testing and red teaming, Sliver has gained traction among threat actors as a stealthier alternative to more heavily signatured frameworks such as Cobalt Strike. As a legitimate framework, its use further complicates detection for security tools that rely on known malicious signatures.
Darktrace’s detection of a ransomware event in a customer’s environment
The initial compromise appears to have occurred via compromised credentials used over the VPN shortly before, or at the onset of the first indicators of suspicious activity. While it remains unclear as to how or when the threat actors gained access to these credentials, the use of initial access brokers (IABs) is a common feature of modern ransomware operations. This suggests that access to the environment may have been established several days or weeks beforehand.
The intrusion unfolded over three days, presenting multiple opportunities for early detection and intervention before ransomware deployment. The attack progressed through a compressed but structured sequence: initial access and reconnaissance were completed within hours, followed by privilege escalation and lateral movement the next day, and culminating in data exfiltration and encryption shortly thereafter. Throughout each stage, distinct behavioral anomalies emerged across the network providing clear indicators of malicious activity well before the ransomware was deployed.
While Darktrace’s Autonomous Response capability was enabled within the customer’s environment, it was not fully configured across the impacted devices, allowing the attack to progress to ransomware deployment. Had Autonomous Response been fully deployed across the affected systems, it could have taken targeted action against the earliest stages of malicious activity, potentially disrupting the intrusion before it escalated.
Figure 1: Timeline of the attack progression.
Day 1: Reconnaissance and privilege escalation
The threat actor gained access via compromised VPN credentials and initiated internal reconnaissance. Darktrace detected anomalous scanning behavior, including unusual port scanning activity and widespread network enumeration.
Specifically, Darktrace detected a high volume of east-west scanning activity across a broad range of ports, with TCP connections targeting ports 21, 80, 445, 4899 and 8080. Associated URIs suggested the use of Nmap, a widely used penetration testing tool. This highlights how attackers often leverage legitimate penetration testing tools for malicious reconnaissance, enabling them to blend into normal network activity and evade traditional signature-based detection methods.
Figure 2: Darktrace's detection of a sharp increase in anomalous internal connections, triggering multiple high-severity model alerts associated with reconnaissance activity.
Several devices were observed using administrative credentials to carry out privileged actions in a manner that was highly anomalous for the environment. This activity was accompanied by behavior consistent with SMB authentication scanning, suggesting efforts to identify and access additional systems. As the activity intensified, an increasing number of devices became involved, signalling lateral movement and further spread across the network.
Darktrace also identified privilege escalation through active directory (AD) replication abuse, specifically via the drsuapi::DRSGetNCChanges function. This technique allows an attacker with sufficient privileges to request directory replication data from a domain controller (DC), enabling them to extract credentials, including password hashes, without directly interacting with user accounts. Commonly associated with ‘DCSync’ attacks, this technique is frequently used to obtain highly privileged credentials and enable further escalation within an environment.
Figure 3: Darktrace’s detection of anomalous AD replication activity indicative of privilege escalation.
This activity was seen alongside the use of the now obsolete SMBv1, repeated NTLM authentication attempts using multiple variations of ‘Administrator’ credentials, reverse DNS scanning, and large-scale network scanning. Darktrace observed widespread use of SMBv1 across the customer’s environment, exposing a significant security weakness. As a legacy protocol with well-documented weaknesses, SMBv1 can be exploited to facilitate lateral movement, allowing the attackers to expand their access following initial compromise.
Day 3: Lateral Movement, Command & Control, and Exfiltration
Two days later, the attacker escalated privileges and expanded their foothold using living-off-the-land (LOTL) techniques such as PSExec, WMI, and RDP. Concurrently, Darktrace identified command-and-control (C2)-style communications consistent with the Sliver framework, alongside rare outbound connections to cloud infrastructure indicating potential data exfiltration. The volume and severity of observed activity increased as attack behavior intensified.
The device was observed conducting extensive lateral movement, leveraging LOTL techniques to evade detection. Activity included WMI execution (e.g. ExecQuery), DCE-RPC activity, SMB sessions and file writes, most of which were successful, as well as the deployment of PSEXESVC.exe via ADMIN$ shares and prolonged RDP sessions. Darktrace identified this behavior as highly anomalous for the environment. Such activity is commonly associated with the transfer of attacker tooling, remote command execution, and the establishment of persistent access across compromised systems.
Figure 4: Darktrace’s detection of a spike in RPC binding events indicative of potential lateral movement.
On the same day, Darktrace detected C2-style SSL communications originating from multiple internal devices to rare external endpoints. These connections exhibited anomalous characteristics, including invalid SSL certificates and repeated connection patterns resembling beaconing. Analysis of the observed JA3 fingerprint further linked the activity to Sliver, the adversary simulation framework referenced earlier, as the hash has previously been associated with Sliver-related infrastructure [3]. The use of this framework reflects a broader trend of attackers repurposing legitimate offensive security tools for stealthy C2 communications. Connections to 137[.]220[.]59[.]55 (ASN AS20473 AS-VULTR) indicated that the communications were likely routed via a virtual private server (VPS) hosted by Vultr. Attackers often utilize VPS infrastructure from legitimate cloud providers like Vultr to obscure their true origin, blend into benign traffic, and evade IP-based detection mechanisms [4].
Figure 5: Darktrace’s Cyber AI Analyst detection of two linked unusual connections to Vultr infrastructure.
Darktrace also observed a device initiating SSL connections to safedata.s3[.]wasabisys[.]com, an endpoint associated with Wasabi cloud storage. Darktrace recognized that neither the destination nor the associated IP address had previously been observed within the environment. More than 200 MB of data was subsequently uploaded externally to endpoints sharing the same JA3 client hash, indicating a sustained transfer session and potential data exfiltration to third-party storage. The apparent exfiltration prior to encryption is consistent with a double-extortion ransomware strategy.
Figure 6: Darktrace’s Cyber AI Analyst detection of more than 30 rare outbound connections to a Wasabi cloud storage endpoint, indicative of potential data exfiltration
Day 4: Encryption
The attack culminated in ransomware deployment, marking the transition from suspicious network activity to a business-impacting incident. Using SMB-based propagation, the threat actor encrypted thousands of files across the network, affecting multiple systems and disrupting normal operations. Throughout the encryption event, the legacy SMBv1 protocol was used extensively across multiple internal systems, resulting in a significant increase in newly encrypted files.
Figure 7: Darktrace’s detection of abnormal spikes in SMB activity and associated model alerts, indicative of ransomware encryption and propagation.
Darktrace’s Cyber AI Analyst automatically investigated and correlated the encryption activity and related events into a single incident narrative, providing the customer with real-time visibility into the attack while significantly reducing investigation time.
Figure 8: Darktrace’s Cyber AI Analyst’s investigation into the encryption activity. AI Analyst incident detailing example encryption activity in real time. Related events are automatically correlated and summarized into a clear narrative, reducing investigation time.
Defender action recommendations
What Could Have Stopped the Attack Earlier?
Although the attack ultimately resulted in ransomware deployment, there were multiple opportunities to detect, contain, and disrupt the intrusion before encryption occurred. The following actions could have significantly reduced the overall impact:
Detect and investigate indicators of reconnaissance and lateral movement
Unusual scanning
Active Directory replication anomalies consistent with DCSync activity
Anomalous use of native tools and processes indicative of LOTL attacks
Unusual use of common reconnaissance tools such as Nmap and NetScan
Contain compromised credentials and affected devices
Disable and reset compromised VPN credentials
Isolate devices performing anomalous scanning and lateral movement activity
Block suspicious external communications and data exfiltration
Use anomaly-based detection to detect and block repeated outbound connections to rare external infrastructure
Prevent data exfiltration to unauthorized cloud storage services such as Wasabi
Conclusion
The incident highlights the importance of anomaly-based detection, particularly against attacks that primarily use native or legitimate tools to evade traditional security measures. Darktrace identified suspicious activity from the first day of the compromise, providing multiple opportunities to disrupt the intrusion before it progressed to lateral movement and data exfiltration.
In this instance, detection was not the limiting factor; response time was. Prompt investigation and containment of devices exhibiting anomalous behavior could have prevented lateral movement, data exfiltration, and ultimately ransomware deployment.
As adversaries increasingly prioritize stealth over custom malware, relying instead on legitimate tools, valid credentials, and trusted infrastructure, traditional signature-based detection becomes less effective. Identifying subtle behavioral deviations early remains critical to disrupting attacks before they escalate into full-scale ransomware incidents.
Credit to Alexandra Evzona (Cyber Analyst), Priya Thapa (Senior Cyber Analyst) Edited by Ryan Traill (Content Manager)
Darktrace / EMAIL Expands Behavioral Defense Across Email and Collaboration Workflows
Email and collaboration tools do more than carry messages. They are where organizations approve payments, share sensitive data, reset credentials, and make thousands of everyday decisions. Increasingly, they are interfaces through which humans direct AI agents in their daily activity. Email, Slack and Teams are high volume, rich with sensitive data, and an easy place to hide malicious activity.
The opportunity isn’t lost on bad actors. Darktrace / EMAIL detected more than 32 million high-confidence phishing emails globally in 2025, and 70% of those messages passed DMARC authentication. Phishing is increasingly difficult to detect and familiar trust signals alone are not enough. People and security teams need to understand how a message fits the normal behavior of the sender, recipient, and organization. They also need to correlate activity across platforms to spot threats that span multiple channels.
To effectively secure against today’s evolved threats, security teams need to act at two levels: they need to help each employee make a safer decision ‘in the moment’, and they need to understand the wider patterns that may expose the business to risk.
Darktrace is introducing four new capabilities in Darktrace / EMAIL to address both challenges. The new features explain suspicious content more clearly to end users, strengthen the capabilities of Darktrace / Adaptive Human Defense with richer guidance, let organizations define their own patterns for detecting sensitive data in messages, and give security teams a process-level view of risk across email and collaboration workflows.
Darktrace / EMAIL Inbox Analysis highlights risky content within your emails
A warning is more useful when it explains what the user should look at. To help do that, we’ve expanded Darktrace / EMAIL’s Inbox Analysis Add-In to highlight potentially dangerous content within the body of emails that Darktrace / EMAIL flags as potentially suspicious or high risk.
The add-in can highlight language designed to create urgency, financial references, requests for payment, suspicious links, and content that is unusual for the sender. Each highlighted element includes a pop up that explains why it may be suspicious. Instead of asking an employee to accept a verdict without context, the analysis helps them examine the message and make a more informed decision.
Enhanced Just-In-Time Training Banners in Darktrace / Adaptive Human Defense
Enhanced Just-In-Time Training Banners build on the same principle. The banners now include a contextual header, actionable advice, and specific detection context. This gives employees more useful guidance at the point of risk without adding unnecessary information or cognitive load.
Together, the capabilities help turn a warning into a short learning moment. Employees can see what looks unusual, understand what action to take, and build their judgment.
Custom Sensitive Data Detection in Darktrace / EMAIL - Data Loss Prevention
Sensitive data is different for every business. Standard categories such as payment card details or government identifiers matter, but organizations also have their own customer codes, project names, research formats, account structures, and internal identifiers.
Custom Sensitive Data Detection in Darktrace / EMAIL - Data Loss Prevention allows administrators to write custom expressions for the data their organization needs to protect. Matched content can trigger existing model actions and data loss prevention (DLP) workflows, extending Darktrace's DLP capabilities.
This extends data loss detection beyond a fixed library of common data types. Security teams can apply controls to information that is sensitive in the context of their own organization and adapt those controls as the business changes.
Introducing Email and Collaboration Workflow Risk Posture Dashboards
Some of the most important risks are not isolated events. They are repeated ways of working that create an opening for error, misuse, or attack. For example, a payment request may be one suspicious message, but a recurring approval workflow that relies on weak verification is a business process risk.
The new Email and Collaboration Workflow Risk Posture Dashboard analyzes email and collaboration data across Email, Microsoft Teams, Slack and Zoom to provide a process-level view of risk in the organization. These may include financial authorization workflows, sensitive data sharing patterns, and activity that could expose credentials.
The dashboard brings these patterns into a view and provides actionable recommendations. This helps security teams determine where to investigate or strengthen controls, where ownership needs to be clarified, and where the business may need to change a risky process. It gives CISOs a clearer view of how human and communication risk is embedded in everyday operations, not only where individual alerts occur.
Behavior connects the individual decision to the wider risk
These capabilities build on Darktrace’s unique behavioral approach to security. We use Adaptive AI to learn how people and AI normally behave within an organization, creating the context needed to recognize when activity changes.
Within the Darktrace Behavioral Defense Platform, Darktrace / EMAIL helps protect people against phishing, account takeover, data exfiltration, and human risk across email and collaboration tools. The new capabilities extend that protection in both directions. They give employees clearer context for the decision in front of them, while giving security leaders a broader view of the workflows and behavior that create risk across the organization.
The result is not simply more alerts. It is a better understanding of why something is risky, what action to take, and where the organization can reduce risk before a familiar process becomes an easy route for an attacker.
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