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 Collaborates with Microsoft: Unifying Email Security with a Shared Vision
Darktrace and Microsoft have joined forces to enhance email security through a new integration, unifying threat response and quarantine capabilities. This collaboration strengthens defenses and streamlines visibility for security teams, reflecting a shared vision for proactive cyber protection.
Why attack-centric approaches to email security can’t cope with modern threats
Despite evolving email threats, many organizations still rely on SEGs or outdated, attack-focused methods. These approaches can’t counter advanced, AI-driven attacks. The solution? Business-centric email security that understands users and inbox behavior, not just threats.
Evaluating Email Security: How to Select the Best Solution for Your Organization
In today’s saturated market for email security, it can be difficult to cut through the noise of AI hype and vendor claims. CISOs should be using a structured evaluation framework to support informed, objective comparisons of different vendors – to allow them to make the best decision for their organization.
Defending the Cloud: Stopping Cyber Threats in Azure and AWS with Darktrace
Real-world intrusions across Azure and AWS
As organizations pursue greater scalability and flexibility, cloud platforms like Microsoft Azure and Amazon Web Services (AWS) have become essential for enabling remote operations and digitalizing corporate environments. However, this shift introduces a new set of security risks, including expanding attack surfaces, misconfigurations, and compromised credentials frequently exploited by threat actors.
This blog dives into three instances of compromise within a Darktrace customer’s Azure and AWS environment which Darktrace.
The first incident took place in early 2024 and involved an attacker compromising a legitimate user account to gain unauthorized access to a customer’s Azure environment.
The other two incidents, taking place in February and March 2025, targeted AWS environments. In these cases, threat actors exfiltrated corporate data, and in one instance, was able to detonate ransomware in a customer’s environment.
Case 1 - Microsoft Azure
Figure 1: Simplified timeline of the attack on a customer’s Azure environment.
In early 2024, Darktrace identified a cloud compromise on the Azure cloud environment of a customer in the Europe, the Middle East and Africa (EMEA) region.
Initial access
In this case, a threat actor gained access to the customer’s cloud environment after stealing access tokens and creating a rogue virtual machine (VM). The malicious actor was found to have stolen access tokens belonging to a third-party external consultant’s account after downloading cracked software.
With these stolen tokens, the attacker was able to authenticate to the customer’s Azure environment and successfully modified a security rule to allow inbound SSH traffic from a specific IP range (i.e., securityRules/AllowCidrBlockSSHInbound). This was likely performed to ensure persistent access to internal cloud resources.
Detection and investigation of the threat
Darktrace / IDENTITY recognized that this activity was highly unusual, triggering the “Repeated Unusual SaaS Resource Creation” alert.
Cyber AI Analyst launched an autonomous investigation into additional suspicious cloud activities occurring around the same time from the same unusual location, correlating the individual events into a broader account hijack incident.
Figure 2: Cyber AI Analyst’s investigation into unusual cloud activity performed by the compromised account.
Figure 3: Surrounding resource creation events highlighted by Cyber AI Analyst.
Figure 4: Surrounding resource creation events highlighted by Cyber AI Analyst.
“Create resource service limit” events typically indicate the creation or modification of service limits (i.e., quotas) for a specific Azure resource type within a region. Meanwhile, “Registers the Capacity Resource Provider” events refer to the registration of the Microsoft Capacity resource provider within an Azure subscription, responsible for managing capacity-related resources, particularly those related to reservations and service limits. These events suggest that the threat actor was looking to create new cloud resources within the environment.
Around ten minutes later, Darktrace detected the threat actor creating or modifying an Azure disk associated with a virtual machine (VM), suggesting an attempt to create a rogue VM within the environment.
Threat actors can leverage such rogue VMs to hijack computing resources (e.g., by running cryptomining malware), maintain persistent access, move laterally within the cloud environment, communicate with command-and-control (C2) infrastructure, and stealthily deliver and deploy malware.
Persistence
Several weeks later, the compromised account was observed sending an invitation to collaborate to an external free mail (Google Mail) address.
Darktrace deemed this activity as highly anomalous, triggering a compliance alert for the customer to review and investigate further.
The next day, the threat actor further registered new multi-factor authentication (MFA) information. These actions were likely intended to maintain access to the compromised user account. The customer later confirmed this activity by reviewing the corresponding event logs within Darktrace.
Case 2 – Amazon Web Services
Figure 5: Simplified timeline of the attack on a customer’s AWS environment
In February 2025, another cloud-based compromised was observed on a UK-based customer subscribed to Darktrace’s Managed Detection and Response (MDR) service.
How the attacker gained access
The threat actor was observed leveraging likely previously compromised credential to access several AWS instances within customer’s Private Cloud environment and collecting and exfiltrating data, likely with the intention of deploying ransomware and holding the data for ransom.
Darktrace alerting to malicious activity
This observed activity triggered a number of alerts in Darktrace, including several high-priority Enhanced Monitoring alerts, which were promptly investigated by Darktrace’s Security Operations Centre (SOC) and raised to the customer’s security team.
The earliest signs of attack observed by Darktrace involved the use of two likely compromised credentials to connect to the customer’s Virtual Private Network (VPN) environment.
Internal reconnaissance
Once inside, the threat actor performed internal reconnaissance activities and staged the Rclone tool “ProgramData\rclone-v1.69.0-windows-amd64.zip”, a command-line program to sync files and directories to and from different cloud storage providers, to an AWS instance whose hostname is associated with a public key infrastructure (PKI) service.
The threat actor was further observed accessing and downloading multiple files hosted on an AWS file server instance, notably finance and investment-related files. This likely represented data gathering prior to exfiltration.
Shortly after, the PKI-related EC2 instance started making SSH connections with the Rclone SSH client “SSH-2.0-rclone/v1.69.0” to a RockHoster Virtual Private Server (VPS) endpoint (193.242.184[.]178), suggesting the threat actor was exfiltrating the gathered data using the Rclone utility they had previously installed. The PKI instance continued to make repeated SSH connections attempts to transfer data to this external destination.
Darktrace’s Autonomous Response
In response to this activity, Darktrace’s Autonomous Response capability intervened, blocking unusual external connectivity to the C2 server via SSH, effectively stopping the exfiltration of data.
This activity was further investigated by Darktrace’s SOC analysts as part of the MDR service. The team elected to extend the autonomously applied actions to ensure the compromise remained contained until the customer could fully remediate the incident.
Continued reconissance
Around the same time, the threat actor continued to conduct network scans using the Nmap tool, operating from both a separate AWS domain controller instance and a newly joined device on the network. These actions were accompanied by further internal data gathering activities, with around 5 GB of data downloaded from an AWS file server.
The two devices involved in reconnaissance activities were investigated and actioned by Darktrace SOC analysts after additional Enhanced Monitoring alerts had triggered.
Lateral movement attempts via RDP connections
Unusual internal RDP connections to a likely AWS printer instance indicated that the threat actor was looking to strengthen their foothold within the environment and/or attempting to pivot to other devices, likely in response to being hindered by Autonomous Response actions.
This triggered multiple scanning, internal data transfer and unusual RDP alerts in Darktrace, as well as additional Autonomous Response actions to block the suspicious activity.
Suspicious outbound SSH communication to known threat infrastructure
Darktrace subsequently observed the AWS printer instance initiating SSH communication with a rare external endpoint associated with the web hosting and VPS provider Host Department (67.217.57[.]252), suggesting that the threat actor was attempting to exfiltrate data to an alternative endpoint after connections to the original destination had been blocked.
Further investigation using open-source intelligence (OSINT) revealed that this IP address had previously been observed in connection with SSH-based data exfiltration activity during an Akira ransomware intrusion [1].
Once again, connections to this IP were blocked by Darktrace’s Autonomous Response and subsequently these blocks were extended by Darktrace’s SOC team.
The above behavior generated multiple Enhanced Monitoring alerts that were investigated by Darktrace SOC analysts as part of the Managed Threat Detection service.
Figure 5: Enhanced Monitoring alerts investigated by SOC analysts as part of the Managed Detection and Response service.
Final containment and collaborative response
Upon investigating the unusual scanning activity, outbound SSH connections, and internal data transfers, Darktrace analysts extended the Autonomous Response actions previously triggered on the compromised devices.
As the threat actor was leveraging these systems for data exfiltration, all outgoing traffic from the affected devices was blocked for an additional 24 hours to provide the customer’s security team with time to investigate and remediate the compromise.
Additional investigative support was provided by Darktrace analysts through the Security Operations Service, after the customer's opened of a ticket related to the unfolding incident.
Figure 8: Simplified timeline of the attack
Around the same time of the compromise in Case 2, Darktrace observed a similar incident on the cloud environment of a different customer.
Initial access
On this occasion, the threat actor appeared to have gained entry into the AWS-based Virtual Private Cloud (VPC) networkvia a SonicWall SMA 500v EC2 instance allowing inbound traffic on any port.
The instance received HTTPS connections from three rare Vultr VPS endpoints (i.e., 45.32.205[.]52, 207.246.74[.]166, 45.32.90[.]176).
Lateral movement and exfiltration
Around the same time, the EC2 instance started scanning the environment and attempted to pivot to other internal systems via RDP, notably a DC EC2 instance, which also started scanning the network, and another EC2 instance.
The latter then proceeded to transfer more than 230 GB of data to the rare external GTHost VPS endpoint 23.150.248[.]189, while downloading hundreds of GBs of data over SMB from another EC2 instance.
Figure 7: Cyber AI Analyst incident generated following the unusual scanning and RDP connections from the initial compromised device.
The same behavior was replicated across multiple EC2 instances, whereby compromised instances uploaded data over internal RDP connections to other instances, which then started transferring data to the same GTHost VPS endpoint over port 5000, which is typically used for Universal Plug and Play (UPnP).
What Darktrace detected
Darktrace observed the threat actor uploading a total of 718 GB to the external endpoint, after which they detonated ransomware within the compromised VPC networks.
This activity generated nine Enhanced Monitoring alerts in Darktrace, focusing on the scanning and external data activity, with the earliest of those alerts triggering around one hour after the initial intrusion.
Darktrace’s Autonomous Response capability was not configured to act on these devices. Therefore, the malicious activity was not autonomously blocked and escalated to the point of ransomware detonation.
Conclusion
This blog examined three real-world compromises in customer cloud environments each illustrating different stages in the attack lifecycle.
The first case showcased a notable progression from a SaaS compromise to a full cloud intrusion, emphasizing the critical role of anomaly detection when legitimate credentials are abused.
The latter two incidents demonstrated that while early detection is vital, the ability to autonomously block malicious activity at machine speed is often the most effective way to contain threats before they escalate.
Together, these incidents underscore the need for continuous visibility, behavioral analysis, and machine-speed intervention across hybrid environments. Darktrace's AI-driven detection and Autonomous Response capabilities, combined with expert oversight from its Security Operations Center, give defenders the speed and clarity they need to contain threats and reduce operational disruption, before the situation spirals.
Credit to Alexandra Sentenac (Senior Cyber Analyst) and Dylan Evans (Security Research Lead)
Top Eight Threats to SaaS Security and How to Combat Them
The latest on the identity security landscape
Following the mass adoption of remote and hybrid working patterns, more critical data than ever resides in cloud applications – from Salesforce and Google Workspace, to Box, Dropbox, and Microsoft 365.
As SaaS applications look set to remain an integral part of the digital estate, organizations are being forced to rethink how they protect their users and data in this area.
What is SaaS security?
SaaS security is the protection of cloud applications. It includes securing the apps themselves as well as the user identities that engage with them.
Below are the top eight threats that target SaaS security and user identities.
1. Account Takeover (ATO)
Attackers gain unauthorized access to a user’s SaaS or cloud account by stealing credentials through phishing, brute-force attacks, or credential stuffing. Once inside, they can exfiltrate data, send malicious emails, or escalate privileges to maintain persistent access.
2. Privilege escalation
Cybercriminals exploit misconfigurations, weak access controls, or vulnerabilities to increase their access privileges within a SaaS or cloud environment. Gaining admin or superuser rights allows attackers to disable security settings, create new accounts, or move laterally across the organization.
3. Lateral movement
Once inside a network or SaaS platform, attackers move between accounts, applications, and cloud workloads to expand their foot- hold. Compromised OAuth tokens, session hijacking, or exploited API connections can enable adversaries to escalate access and exfiltrate sensitive data.
4. Multi-Factor Authentication (MFA) bypass and session hijacking
Threat actors bypass MFA through SIM swapping, push bombing, or exploiting session cookies. By stealing an active authentication session, they can access SaaS environments without needing the original credentials or MFA approval.
5. OAuth token abuse
Attackers exploit OAuth authentication mechanisms by stealing or abusing tokens that grant persistent access to SaaS applications. This allows them to maintain access even if the original user resets their password, making detection and mitigation difficult.
6. Insider threats
Malicious or negligent insiders misuse their legitimate access to SaaS applications or cloud platforms to leak data, alter configurations, or assist external attackers. Over-provisioned accounts and poor access control policies make it easier for insiders to exploit SaaS environments.
SaaS applications rely on APIs for integration and automation, but attackers exploit insecure endpoints, excessive permissions, and unmonitored API calls to gain unauthorized access. API abuse can lead to data exfiltration, privilege escalation, and service disruption.
8. Business Email Compromise (BEC) via SaaS
Adversaries compromise SaaS-based email platforms (e.g., Microsoft 365 and Google Workspace) to send phishing emails, conduct invoice fraud, or steal sensitive communications. BEC attacks often involve financial fraud or data theft by impersonating executives or suppliers.
BEC heavily uses social engineering techniques, tailoring messages for a specific audience and context. And with the growing use of generative AI by threat actors, BEC is becoming even harder to detect. By adding ingenuity and machine speed, generative AI tools give threat actors the ability to create more personalized, targeted, and convincing attacks at scale.
Protecting against these SaaS threats
Traditionally, security leaders relied on tools that were focused on the attack, reliant on threat intelligence, and confined to a single area of the digital estate.
However, these tools have limitations, and often prove inadequate for contemporary situations, environments, and threats. For example, they may lack advanced threat detection, have limited visibility and scope, and struggle to integrate with other tools and infrastructure, especially cloud platforms.
AI-powered SaaS security stays ahead of the threat landscape
New, more effective approaches involve AI-powered defense solutions that understand the digital business, reveal subtle deviations that indicate cyber-threats, and action autonomous, targeted responses.
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