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April 30, 2024

Detecting Attacks Across Email, SaaS, and Network Environments with Darktrace’s ActiveAI Security Platform

This blog explores how Darktrace’s combined AI approach enabled it to identify and connect an attack that took place over three critical areas of a customer’s digital environment, namely email, SaaS and network.
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
Zoe Tilsiter
Cyber Analyst
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30
Apr 2024

The State of AI in Cybersecurity

In a recent survey outlined in Darktrace’s State of AI Cyber Security whitepaper, 95% of cyber security professionals agree that AI-powered security solutions will improve their organization’s detection of cyber-threats [1]. Crucially, a combination of multiple AI methods is the most effective to improve cybersecurity; improving threat detection, accelerating threat investigation and response, and providing visibility across an organization’s digital environment.

In March 2024, Darktrace’s AI-led security platform was able to detect suspicious activity affecting a customer’s email, Software-as-a-Service (SaaS), and network environments, whilst its applied supervised learning capability, Cyber AI Analyst, autonomously correlated and connected all of these events together in one single incident, explained concisely using natural language processing.

Attack Overview

Following an initial email attack vector, an attacker logged into a compromised SaaS user account from the Netherlands, changed inbox rules, and leveraged the account to send thousands of phishing emails to internal and external users. Internal users fell victim to the emails by clicking on contained suspicious links that redirected them to newly registered suspicious domains hosted on same IP address as the hijacked SaaS account login. This activity triggered multiple alerts in Darktrace DETECT™ on both the network and SaaS side, all of which were correlated into one Cyber AI Analyst incident.

In this instance, Darktrace RESPOND™ was not active on any of the customer’s environments, meaning the compromise was able to escalate until their security team acted on the alerts raised by DETECT. Had RESPOND been enabled at the time of the attack, it would have been able to apply swift actions to contain the attack by blocking connections to suspicious endpoints on the network side and disabling users deviating from their normal behavior on the customer’s SaaS environment.

Nevertheless, thanks to DETECT and Cyber AI Analyst, Darktrace was able to provide comprehensive visibility across the customer’s three digital estate environments, decreasing both investigation and response time which enabled them to quickly enact remediation during the attack. This highlights the crucial role that Darktrace’s combined AI approach can play in anomaly detection cyber defense

Attack Details & Darktrace Coverage

Attack timeline

1. Email: the initial attack vector  

The initial attack vector was likely email, as on March 18, 2024, Darktrace observed a user device making several connections to the email provider “zixmail[.]net”, shortly before it connected to the first suspicious domain. Darktrace/Email identified multiple unusual inbound emails from an unknown sender that contained a suspicious link. Darktrace recognized these emails as potentially malicious and locked the link, ensuring that recipients could not directly click it.

Figure 1: Suspected initial compromise email from an unknown sender, containing a suspicious link, which was locked by Darktrace/Email.

2. Escalation to Network

Later that day, despite Darktrace/Email having locked the link in the suspicious email, the user proceeded to click on it and was directed to a suspicious external location, namely “rz8js7sjbef[.]latovafineart[.]life”, which triggered the Darktrace/Network DETECT model “Suspicious Domain”. Darktrace/Email was able to identify that this domain had only been registered 4 days before this activity and was hosted on an IP address based in the Netherlands, 193.222.96[.]9.

3. SaaS Account Hijack

Just one minute later, Darktrace/Apps observed the user’s Microsoft 365 account logging into the network from the same IP address. Darktrace understood that this represented unusual SaaS activity for this user, who had only previously logged into the customer’s SaaS environment from the US, triggering the “Unusual External Source for SaaS Credential Use” model.

4. SaaS Account Updates

A day later, Darktrace identified an unusual administrative change on the user’s Microsoft 365 account. After logging into the account, the threat actor was observed setting up a new multi-factor authentication (MFA) method on Microsoft Authenticator, namely requiring a 6-digit code to authenticate. Darktrace understood that this authentication method was different to the methods previously used on this account; this, coupled with the unusual login location, triggered the “Unusual Login and Account Update” DETECT model.

5. Obfuscation Email Rule

On March 20, Darktrace detected the threat actor creating a new email rule, named “…”, on the affected account. Attackers are typically known to use ambiguous or obscure names when creating new email rules in order to evade the detection of security teams and endpoints users.

The parameters for the email rule were:

“AlwaysDeleteOutlookRulesBlob: False, Force: False, MoveToFolder: RSS Feeds, Name: ..., MarkAsRead: True, StopProcessingRules: True.”

This rule was seemingly created with the intention of obfuscating the sending of malicious emails, as the rule would move sent emails to the "RSS Feeds” folder, a commonly used tactic by attackers as the folder is often left unchecked by endpoint users. Interestingly, Darktrace identified that, despite the initial unusual login coming from the Netherlands, the email rule was created from a different destination IP, indicating that the attacker was using a Virtual Private Network (VPN) after gaining a foothold in the network.

Hijacked SaaS account making an anomalous login from the unusual Netherlands-based IP, before creating a new email rule.
Figure 2: Hijacked SaaS account making an anomalous login from the unusual Netherlands-based IP, before creating a new email rule.

6. Outbound Phishing Emails Sent

Later that day, the attacker was observed using the compromised customer account to send out numerous phishing emails to both internal and external recipients. Darktrace/Email detected a significant spike in inbound emails on the compromised account, with the account receiving bounce back emails or replies in response to the phishing emails. Darktrace further identified that the phishing emails contained a malicious DocSend link hidden behind the text “Click Here”, falsely claiming to be a link to the presentation platform Prezi.

Figure 3: Darktrace/Email detected that the DocSend link displayed via text “Click Here”, was embedded in a Prezi link.
Figure 3: Darktrace/Email detected that the DocSend link displayed via text “Click Here”, was embedded in a Prezi link.

7. Suspicious Domains and Redirects

After the phishing emails were sent, multiple other internal users accessed the DocSend link, which directed them to another suspicious domain, “thecalebgroup[.]top”, which had been registered on the same day and was hosted on the aforementioned Netherlands-based IP, 193.222.96[.]91. At the time of the attack, this domain had not been reported by any open-source intelligence (OSINT), but it has since been flagged as malicious by multiple vendors [2].

External Sites Summary showing the suspicious domain that had never previously been seen on the network. A total of 11 “Suspicious Domain” models were triggered in response to this activity.
Figure 4: External Sites Summary showing the suspicious domain that had never previously been seen on the network. A total of 11 “Suspicious Domain” models were triggered in response to this activity.  

8. Cyber AI Analyst’s Investigation

As this attack was unfolding, Darktrace’s Cyber AI Analyst was able to autonomously investigate the events, correlating them into one wider incident and continually adding a total of 14 new events to the incident as more users fell victim to the phishing links.

Cyber AI Analyst successfully weaved together the initial suspicious domain accessed in the initial email attack vector (Figure 5), the hijack of the SaaS account from the Netherlands IP (Figure 6), and the connection to the suspicious redirect link (Figure 7). Cyber AI Analyst was also able to uncover other related activity that took place at the time, including a potential attempt to exfiltrate data out of the customer’s network.

By autonomously analyzing the thousands of connections taking place on a network at any given time, Darktrace’s Cyber AI Analyst is able to detect seemingly separate anomalous events and link them together in one incident. This not only provides organizations with full visibility over potential compromises on their networks, but also saves their security teams precious time ensuring they can quickly scope out the ongoing incident and begin remediation.

Figure 5: Cyber AI Analyst correlated the attack’s sequence, starting with the initial suspicious domain accessed in the initial email attack vector.
Figure 5: Cyber AI Analyst correlated the attack’s sequence, starting with the initial suspicious domain accessed in the initial email attack vector.
Figure 6: As the attack progressed, Cyber AI Analyst correlated and appended additional events to the same incident, including the SaaS account hijack from the Netherlands-based IP.
Figure 6: As the attack progressed, Cyber AI Analyst correlated and appended additional events to the same incident, including the SaaS account hijack from the Netherlands-based IP.
Cyber AI Analyst correlated and appended additional events to the same incident, including additional users connecting to the suspicious redirect link following the outbound phishing emails being sent.
Figure 7: Cyber AI Analyst correlated and appended additional events to the same incident, including additional users connecting to the suspicious redirect link following the outbound phishing emails being sent.

Conclusion

In this scenario, Darktrace demonstrated its ability to detect and correlate suspicious activities across three critical areas of a customer’s digital environment: email, SaaS, and network.

It is essential that cyber defenders not only adopt AI but use a combination of AI technology capable of learning and understanding the context of an organization’s entire digital infrastructure. Darktrace’s anomaly-based approach to threat detection allows it to identify subtle deviations from the expected behavior in network devices and SaaS users, indicating potential compromise. Meanwhile, Cyber AI Analyst dynamically correlates related events during an ongoing attack, providing organizations and their security teams with the information needed to respond and remediate effectively.

Credit to Zoe Tilsiter, Analyst Consulting Lead (EMEA), Brianna Leddy, Director of Analysis

Appendices

References

[1] https://darktrace.com/state-of-ai-cyber-security

[2] https://www.virustotal.com/gui/domain/thecalebgroup.top

Darktrace DETECT Model Coverage

SaaS Models

- SaaS / Access / Unusual External Source for SaaS Credential Use

- SaaS / Compromise / Unusual Login and Account Update

- SaaS / Compliance / Anomalous New Email Rule

- SaaS / Compromise / Unusual Login and New Email Rule

Network Models

- Device / Suspicious Domain

- Multiple Device Correlations / Multiple Devices Breaching Same Model

Cyber AI Analyst Incidents

- Possible Hijack of Office365 Account

- Possible SSL Command and Control

Indicators of Compromise (IoCs)

IoC – Type – Description

193.222.96[.]91 – IP – Unusual Login Source

thecalebgroup[.]top – Domain – Possible C2 Endpoint

rz8js7sjbef[.]latovafineart[.]life – Domain – Possible C2 Endpoint

https://docsend[.]com/view/vcdmsmjcskw69jh9 - Domain - Phishing Link

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
Zoe Tilsiter
Cyber Analyst

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June 18, 2025

Darktrace Collaborates with Microsoft: Unifying Email Security with a Shared Vision

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In today’s threat landscape, email remains the most targeted vector for cyberattacks. Organizations require not only multi-layered defenses but also advanced, integrated systems that work collaboratively to proactively mitigate threats before they cause damage

That’s why we’re proud to announce a new integration between Darktrace / EMAIL and Microsoft Defender for Office 365, delivering a Unified Quarantine experience that empowers security teams with seamless visibility, control, and response across both platforms.

This announcement builds on a strong and growing collaboration. In 2024, Darktrace was honored as Microsoft UK Partner of the Year and recognized as a Security Trailblazer at the annual Microsoft Security 20/20 Awards, a testament to our shared commitment to innovation and customer-centric security.

A Shared Mission: Stopping Threats at Machine Speed

This integration is more than a technical milestone,as it’s a reflection of a shared mission: to protect organizations from both known and unknown threats, with efficiency, accuracy, and transparency.

  • Microsoft Defender for Office 365 delivers a comprehensive security framework that safeguards Microsoft 365 email and collaboration workloads leveraging advanced AI, global threat intelligence and information on known attack infrastructure.
  • Darktrace / EMAIL complements this with Self-Learning AI that understands the unique communication patterns within each organization, detecting subtle anomalies that evade traditional detection methods.

Together, we’re delivering multi-layered, adaptive protection that’s greater than the sum of its parts.

“Our integration with Microsoft gives security teams the tools they need to act faster and more precisely to detect and respond to threats,” said Jill Popelka, CEO of Darktrace. “Together, we’re strengthening defenses where it matters most to our customers: at the inbox.”

Unified Quarantine: One View, Total Clarity

The new Unified Quarantine experience gives customers a single pane of glass to view and manage email threatsregardless of which product took action. This means:

  • Faster investigations with consolidated visibility
  • Clear attribution of actions and outcomes across both platforms
  • Streamlined workflows for security teams managing complex environments

“This integration is a testament to the power of combining Microsoft’s global threat intelligence with Darktrace’s unique ability to understand the ‘self’ of an organization,” said Jack Stockdale, CTO of Darktrace. “Together, we’re delivering a new standard in proactive, adaptive email security.”

A New Era of Collaborative Cyber Defense

This collaboration represents a broader shift in cybersecurity: from siloed tools to integrated ecosystems. As attackers become more sophisticated, defenders must move faster, smarter, and in unison.

Through this integration, Darktrace and Microsoft establish a new standard for collaboration between native and third-party security solutions, enhancing not only threat detection but also comprehensive understanding and proactive measures against threats.

We’re excited to bring this innovation to our customers and continue building a future where AI and human expertise collaborate to secure the enterprise.

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Carlos Gray
Senior Product Marketing Manager, Email

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June 18, 2025

Customer Case Study: Leading Petrochemical Manufacturer

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Headquartered in Saudi Arabia, this industry leading petrochemical manufacturer serves customers in more than 80 countries across diverse markets throughout Europe, Africa, Latin America, the Middle East, China, and Southeast Asia.

Cyber resiliency critical to growth strategy

This leading petrochemical manufacturer’s vision is to be one of the major global players in the production and marketing of designated petrochemicals and downstream products. The company aims to significantly increase its capacity to up to a million metric tons within the next few years.

With cyber-attacks on critical infrastructure increasing 30% globally last year, cyber resiliency is essential to supporting the company’s strategic business goals of:

  • Maximizing production through efficient asset utilization
  • Maximizing sales by conducting 90% of its business outside Saudi Arabia
  • Optimizing resources and processes by integrating with UN Global Compact principles for sustainability and efficiency
  • Growing its business portfolio by engaging in joint ventures to diversify production and add value to the economy

However, the industry leader faced several challenges in its drive to fortify its cybersecurity defenses.

Visibility gaps delay response time

The company’s existing security setup provided limited visibility to the in-house security team, hindering its ability to detect anomalous network and user activity in real time. This resulted in delayed responses to potential incidents, making proactive issue resolution difficult and any remediation in the event of a successful attack costly and time-consuming.

Manual detection drains resources

Without automated detection and response capabilities, the organization’s security team had to manually monitor for suspicious activity – a time-consuming and inefficient approach that strained resources and left the organization vulnerable. This made it difficult for the team to stay current with training or acquire new skills and certifications, which are core to the ethos of both the company’s owners and the team itself.

Cyber-attacks on critical infrastructure increasing

The petrochemical manufacturer is part of a broader ecosystem of companies, making the protection of its supply chain – both upstream and downstream – critical. With several manufacturing entities and multiple locations, the customer’s internal structure is complex and challenging to secure. As cyber-attacks on critical infrastructure escalate, it needed a more comprehensive approach to safeguard its business and the wider ecosystem.

Keeping and growing skills and focus in-house

To strengthen its cybersecurity strategy, the company considered two options:

  1. Make a significant initial and ongoing investment in a Security Operations Center (SOC), which would involve skills development outside the company and substantial management overhead.
  2. Use a combination of new, automated tools and an outsourced Managed Detection and Response (MDR) service to reduce the burden on internal security specialists and allow the company to invest in upskilling its staff so they can focus on more strategic tasks.

Faced with this choice between entirely outsourcing security and augmenting the security team with new capabilities, the customer chose the second option, selecting Darktrace to automate the company’s monitoring, detection, and response. Today, the petrochemical manufacturer is using:

Extending the SOC with 24/7 expert support

To alleviate the burden on its lean security team, the company augmented its in-house capabilities with Darktrace’s Managed Detection & Response service. This support acts as an extension of its SOC, providing 24/7 monitoring, investigation, and escalation of high-priority threats. With Darktrace’s global SOC managing alert triage and autonomously containing threats, the organization’s internal team can focus on strategic initiatives. The result is a stronger security posture and increased capacity to proactively address evolving cyber risks – without expanding headcount or sacrificing visibility.

A unique approach to AI

In its search for a new security platform, the company’s Director of Information Technology said Darktrace’s autonomous response capability, coupled with Self-Learning AI-driven threat reduction, were two big reasons for selecting Darktrace over competing products and services.

AI was a huge factor – no one else was doing what Darktrace was doing with [AI].”

Demonstrated visibility

Before Darktrace, the customer had no visibility into the network activity to and from remote worker devices. Some employees need the ability to connect to its networks at any time and from any location, including the Director of Information Technology. The trial deployment of Darktrace / ENDPOINT was a success and gave the team peace of mind that, no matter the location or device, high-value remote workers were protected by Darktrace.

Modular architecture  

Darktrace's modular architecture allowed the company to deploy security controls across its complex, multi-entity environment. The company’s different locations run on segregated networks but are still interconnected and need to be protected. Darktrace / NETWORK provides a unified view and coordinated security response across the organization’s entire network infrastructure, including endpoint devices.

Results

The petrochemical manufacturer is using Darktrace across all of its locations and has achieved total visibility across network and user activity. “Darktrace is increasing in value every day,” said the Director of Information Technology.

I don’t have a big team, and Darktrace makes our lives very, very easy, not least the automation of some of the tasks that require constant manual review.”

Time savings frees analysts to focus on proactive security

Darktrace / NETWORK provides continuous, AI-driven monitoring and analysis of the company’s network activity, user behavior, and threat patterns, establishing a baseline of what normal activity looks like, and then alerting analysts to any deviations from normal traffic, activity, and behaviors. Darktrace’s autonomous response capabilities speed up response to detected threats, meaning intervention from the security team is required for fewer incidents and alerts.

In October 2024 alone, Darktrace Cyber AI Analyst saved the team 810 investigation hours, and autonomously responded to 180 anomalous behaviors that were uncovered during the investigations. With Darktrace managing the majority of threat detection and response efforts, the security team has been able to change its day-to-day activity from manual review of traffic and alerts and belated response to activity, to proactively fortifying its detection and response posture and upskilling to meet evolving requirements.  

Layered email protection reduces phishing threats

The company’s email infrastructure posed a challenge due to petrochemical industry regulations requiring on-premises email servers, with some security delivered via Microsoft Azure. By integrating Darktrace / EMAIL into the Azure stack, the organization has reduced the volume of phishing emails its users receive by 5%.

“Now we have one more layer of security related to email – every email goes through two filters. If something is not being caught or traced by Azure, it is being detected by Darktrace,” said the Director of Information Technology. “As a result, we’re now seeing only about 15% to 20% of the phishing emails we used to receive before implementing Darktrace.”

Preparing for a secure future

The time saved using Darktrace has helped the security team take proactive steps, including preparing for new cyber resilience regulations for Saudi Arabia’s Critical National Infrastructure, as mandated by the National Cybersecurity Authority (NCA).

“The team now has ample time to prepare policies and procedures that meet the new NCA regulations and, in some cases, enhance the requirements of the new law,” said the Director of Information Technology. “All of this is possible because they don’t need to keep watch; Darktrace takes on so much of that task for them.”

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