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April 30, 2024

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

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30
Apr 2024
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.

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.

Suspected initial compromise email from an unknown sender, containing a suspicious link, which was locked by Darktrace/Email.
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.
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Zoe Tilsiter
Cyber Analyst
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January 29, 2025

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Inside the SOC

Bytesize Security: Insider Threats in Google Workspace

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What is an insider threat?

An insider threat is a cyber risk originating from within an organization. These threats can involve actions such as an employee inadvertently clicking on a malicious link (e.g., a phishing email) or an employee with malicious intent conducting data exfiltration for corporate sabotage.

Insiders often exploit their knowledge and access to legitimate corporate tools, presenting a continuous risk to organizations. Defenders must protect their digital estate against threats from both within and outside the organization.

For example, in the summer of 2024, Darktrace / IDENTITY successfully detected a user in a customer environment attempting to steal sensitive data from a trusted Google Workspace service. Despite the use of a legitimate and compliant corporate tool, Darktrace identified anomalies in the user’s behavior that indicated malicious intent.

Attack overview: Insider threat

In June 2024, Darktrace detected unusual activity involving the Software-as-a-Service (SaaS) account of a former employee from a customer organization. This individual, who had recently left the company, was observed downloading a significant amount of data in the form of a “.INDD” file (an Adobe InDesign document typically used to create page layouts [1]) from Google Drive.

While the use of Google Drive and other Google Workspace platforms was not unexpected for this employee, Darktrace identified that the user had logged in from an unfamiliar and suspicious IPv6 address before initiating the download. This anomaly triggered a model alert in Darktrace / IDENTITY, flagging the activity as potentially malicious.

A Model Alert in Darktrace / IDENTITY showing the unusual “.INDD” file being downloaded from Google Workspace.
Figure 1: A Model Alert in Darktrace / IDENTITY showing the unusual “.INDD” file being downloaded from Google Workspace.

Following this detection, the customer reached out to Darktrace’s Security Operations Center (SOC) team via the Security Operations Support service for assistance in triaging and investigating the incident further. Darktrace’s SOC team conducted an in-depth investigation, enabling the customer to identify the exact moment of the file download, as well as the contents of the stolen documents. The customer later confirmed that the downloaded files contained sensitive corporate data, including customer details and payment information, likely intended for reuse or sharing with a new employer.

In this particular instance, Darktrace’s Autonomous Response capability was not active, allowing the malicious insider to successfully exfiltrate the files. If Autonomous Response had been enabled, Darktrace would have immediately acted upon detecting the login from an unusual (in this case 100% rare) location by logging out and disabling the SaaS user. This would have provided the customer with the necessary time to review the activity and verify whether the user was authorized to access their SaaS environments.

Conclusion

Insider threats pose a significant challenge for traditional security tools as they involve internal users who are expected to access SaaS platforms. These insiders have preexisting knowledge of the environment, sensitive data, and how to make their activities appear normal, as seen in this case with the use of Google Workspace. This familiarity allows them to avoid having to use more easily detectable intrusion methods like phishing campaigns.

Darktrace’s anomaly detection capabilities, which focus on identifying unusual activity rather than relying on specific rules and signatures, enable it to effectively detect deviations from a user’s expected behavior. For instance, an unusual login from a new location, as in this example, can be flagged even if the subsequent malicious activity appears innocuous due to the use of a trusted application like Google Drive.

Credit to Vivek Rajan (Cyber Analyst) and Ryan Traill (Analyst Content Lead)

Appendices

Darktrace Model Detections

SaaS / Resource::Unusual Download Of Externally Shared Google Workspace File

References

[1]https://www.adobe.com/creativecloud/file-types/image/vector/indd-file.html

MITRE ATT&CK Mapping

Technqiue – Tactic – ID

Data from Cloud Storage Object – COLLECTION -T1530

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Vivek Rajan
Cyber Analyst

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January 28, 2025

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Reimaginar su SOC: cómo lograr una seguridad de red proactiva

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Introduction: Challenges and solutions to SOC efficiency

For Security Operation Centers (SOCs), reliance on signature or rule-based tools – solutions that are always chasing the latest update to prevent only what is already known – creates an excess of false positives. SOC analysts are therefore overwhelmed by a high volume of context-lacking alerts, with human analysts able to address only about 10% due to time and resource constraints. This forces many teams to accept the risks of addressing only a fraction of the alerts while novel threats go completely missed.

74% of practitioners are already grappling with the impact of an AI-powered threat landscape, which amplifies challenges like tool sprawl, alert fatigue, and burnout. Thus, achieving a resilient network, where SOC teams can spend most of their time getting proactive and stopping threats before they occur, feels like an unrealistic goal as attacks are growing more frequent.

Despite advancements in security technology (advanced detection systems with AI, XDR tools, SIEM aggregators, etc...), practitioners are still facing the same issues of inefficiency in their SOC, stopping them from becoming proactive. How can they select security solutions that help them achieve a proactive state without dedicating more human hours and resources to managing and triaging alerts, tuning rules, investigating false positives, and creating reports?

To overcome these obstacles, organizations must leverage security technology that is able to augment and support their teams. This can happen in the following ways:

  1. Full visibility across the modern network expanding into hybrid environments
  2. Have tools that identifies and stops novel threats autonomously, without causing downtime
  3. Apply AI-led analysis to reduce time spent on manual triage and investigation

Your current solutions might be holding you back

Traditional cybersecurity point solutions are reliant on using global threat intelligence to pattern match, determine signatures, and consequently are chasing the latest update to prevent only what is known. This means that unknown threats will evade detection until a patient zero is identified. This legacy approach to threat detection means that at least one organization needs to be ‘patient zero’, or the first victim of a novel attack before it is formally identified.

Even the point solutions that claim to use AI to enhance threat detection rely on a combination of supervised machine learning, deep learning, and transformers to

train and inform their systems. This entails shipping your company’s data out to a large data lake housed somewhere in the cloud where it gets blended with attack data from thousands of other organizations. The resulting homogenized dataset gets used to train AI systems — yours and everyone else’s — to recognize patterns of attack based on previously encountered threats.

While using AI in this way reduces the workload of security teams who would traditionally input this data by hand, it emanates the same risk – namely, that AI systems trained on known threats cannot deal with the threats of tomorrow. Ultimately, it is the unknown threats that bring down an organization.

The promise and pitfalls of XDR in today's threat landscape

Enter Extended Detection and Response (XDR): a platform approach aimed at unifying threat detection across the digital environment. XDR was developed to address the limitations of traditional, fragmented tools by stitching together data across domains, providing SOC teams with a more cohesive, enterprise-wide view of threats. This unified approach allows for improved detection of suspicious activities that might otherwise be missed in siloed systems.

However, XDR solutions still face key challenges: they often depend heavily on human validation, which can aggravate the already alarmingly high alert fatigue security analysts experience, and they remain largely reactive, focusing on detecting and responding to threats rather than helping prevent them. Additionally, XDR frequently lacks full domain coverage, relying on EDR as a foundation and are insufficient in providing native NDR capabilities and visibility, leaving critical gaps that attackers can exploit. This is reflected in the current security market, with 57% of organizations reporting that they plan to integrate network security products into their current XDR toolset[1].

Why settling is risky and how to unlock SOC efficiency

The result of these shortcomings within the security solutions market is an acceptance of inevitable risk. From false positives driving the barrage of alerts, to the siloed tooling that requires manual integration, and the lack of multi-domain visibility requiring human intervention for business context, security teams have accepted that not all alerts can be triaged or investigated.

While prioritization and processes have improved, the SOC is operating under a model that is overrun with alerts that lack context, meaning that not all of them can be investigated because there is simply too much for humans to parse through. Thus, teams accept the risk of leaving many alerts uninvestigated, rather than finding a solution to eliminate that risk altogether.

Darktrace / NETWORK is designed for your Security Operations Center to eliminate alert triage with AI-led investigations , and rapidly detect and respond to known and unknown threats. This includes the ability to scale into other environments in your infrastructure including cloud, OT, and more.

Beyond global threat intelligence: Self-Learning AI enables novel threat detection & response

Darktrace does not rely on known malware signatures, external threat intelligence, historical attack data, nor does it rely on threat trained machine learning to identify threats.

Darktrace’s unique Self-learning AI deeply understands your business environment by analyzing trillions of real-time events that understands your normal ‘pattern of life’, unique to your business. By connecting isolated incidents across your business, including third party alerts and telemetry, Darktrace / NETWORK uses anomaly chains to identify deviations from normal activity.

The benefit to this is that when we are not predefining what we are looking for, we can spot new threats, allowing end users to identify both known threats and subtle, never-before-seen indicators of malicious activity that traditional solutions may miss if they are only looking at historical attack data.

AI-led investigations empower your SOC to prioritize what matters

Anomaly detection is often criticized for yielding high false positives, as it flags deviations from expected patterns that may not necessarily indicate a real threat or issues. However, Darktrace applies an investigation engine to automate alert triage and address alert fatigue.

Darktrace’s Cyber AI Analyst revolutionizes security operations by conducting continuous, full investigations across Darktrace and third-party alerts, transforming the alert triage process. Instead of addressing only a fraction of the thousands of daily alerts, Cyber AI Analyst automatically investigates every relevant alert, freeing up your team to focus on high-priority incidents and close security gaps.

Powered by advanced machine-learning techniques, including unsupervised learning, models trained by expert analysts, and tailored security language models, Cyber AI Analyst emulates human investigation skills, testing hypotheses, analyzing data, and drawing conclusions. According to Darktrace Internal Research, Cyber AI Analyst typically provides a SOC with up to  50,000 additional hours of Level 2 analysis and written reporting annually, enriching security operations by producing high level incident alerts with full details so that human analysts can focus on Level 3 tasks.

Containing threats with Autonomous Response

Simply quarantining a device is rarely the best course of action - organizations need to be able to maintain normal operations in the face of threats and choose the right course of action. Different organizations also require tailored response functions because they have different standards and protocols across a variety of unique devices. Ultimately, a ‘one size fits all’ approach to automated response actions puts organizations at risk of disrupting business operations.

Darktrace’s Autonomous Response tailors its actions to contain abnormal behavior across users and digital assets by understanding what is normal and stopping only what is not. Unlike blanket quarantines, it delivers a bespoke approach, blocking malicious activities that deviate from regular patterns while ensuring legitimate business operations remain uninterrupted.

Darktrace offers fully customizable response actions, seamlessly integrating with your workflows through hundreds of native integrations and an open API. It eliminates the need for costly development, natively disarming threats in seconds while extending capabilities with third-party tools like firewalls, EDR, SOAR, and ITSM solutions.

Unlocking a proactive state of security

Securing the network isn’t just about responding to incidents — it’s about being proactive, adaptive, and prepared for the unexpected. The NIST Cybersecurity Framework (CSF 2.0) emphasizes this by highlighting the need for focused risk management, continuous incident response (IR) refinement, and seamless integration of these processes with your detection and response capabilities.

Despite advancements in security technology, achieving a proactive posture is still a challenge to overcome because SOC teams face inefficiencies from reliance on pattern-matching tools, which generate excessive false positives and leave many alerts unaddressed, while novel threats go undetected. If SOC teams are spending all their time investigating alerts then there is no time spent getting ahead of attacks.

Achieving proactive network resilience — a state where organizations can confidently address challenges at every stage of their security posture — requires strategically aligned solutions that work seamlessly together across the attack lifecycle.

References

1.       Market Guide for Extended Detection and Response, Gartner, 17thAugust 2023 - ID G00761828

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