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October 24, 2024

Phishing and Persistence: Darktrace’s Role in Defending Against a Sophisticated Account Takeover

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24
Oct 2024
In a recent incident, Darktrace uncovered a M365 account takeover attempt targeting a company in the manufacturing industry. The attacker executed a sophisticated phishing attack, gaining access through the organization’s SaaS platform. This allowed the threat actor to create a new inbox rule, potentially setting the stage for future compromises.

The exploitation of SaaS platforms

As businesses continue to grow and evolve, the need for sharing ideas through productivity and cloud Software-as-a-Service (SaaS) platforms is becoming increasingly crucial. However, these platforms have also become prime targets for cyber attackers.

Threat actors often exploit these widely-used services to gain unauthorized access, steal sensitive information, and disrupt business operations. The growing reliance on SaaS platforms makes them attractive entry points for cybercriminals, who use sophisticated techniques such as phishing, social engineering, and malware to compromise these systems.

Services like Microsoft 365 are regularly targeted by threat actors looking for an entry point into an organization’s environment to carry out malicious activities. Securing these platforms is crucial to protect business data and ensure operational continuity.

Darktrace / EMAIL detection of the phishing attack

In a recent case, Darktrace observed a customer in the manufacturing sector receiving a phishing email that led to a threat actor logging in and creating an email rule. Threat actors often create email rules to move emails to their inbox, avoiding detection. Additionally, Darktrace detected a spoofed domain registered by the threat actor. Despite already having access to the customer’s SaaS account, the actor seemingly registered this domain to maintain persistence on the network, allowing them to communicate with the spoofed domain and conduct further malicious activity.

Darktrace / EMAIL can help prevent compromises like this one by blocking suspicious emails as soon as they are identified. Darktrace’s AI-driven email detection and response recognizes anomalies that might indicate phishing attempts and applies mitigative actions autonomously to prevent the escalation of an attack.

Unfortunately, in this case, Darktrace was not configured in Autonomous Response mode at the time of the attack, meaning actions had to be manually applied by the customer’s security team. Had it been fully enabled, it would have held the emails, preventing them from reaching the intended recipient and stopping the attack at its inception.

However, Darktrace’s Managed Threat Detection alerted the Security Operations Center (SOC) team to the compromise, enabling them to thoroughly investigate the incident and notify the customer before further damage could occur.

The Managed Threat Detection service continuously monitors customer networks for suspicious activities that may indicate an emerging threat. When such activities are detected, alerts are sent to Darktrace’s expert Cyber Analysts for triage, significantly speeding up the remediation process.

Attack Overview

On May 2, 2024, Darktrace detected a threat actor targeting a customer in the manufacturing sector then an unusual login to their SaaS environment was observed prior to the creation of a new email rule.

Darktrace immediately identified the login as suspicious due to the rarity of the source IP (31.222.254[.]27) and ASN, coupled with the absence of multi-factor authentication (MFA), which was typically required for this account.

The new email rule was intended to mark emails as read and moved to the ‘Conversation History’ folder for inbound emails from a specific domain. The rule was named “….,,,”, likely the attacker attempting to setup their new rule with an unnoteworthy name to ensure it would not be noticed by the account’s legitimate owner. Likewise, by moving emails from a specific domain to ‘Conversation History’, a folder that is rarely used by most users, any phishing emails sent by that domain would remain undetected by the user.

Darktrace’s detection of the unusual SaaS login and subsequent creation of the new email rule “….,,,”.
Figure 1: Darktrace’s detection of the unusual SaaS login and subsequent creation of the new email rule “….,,,”.

The domain in question was identified as being newly registered and an example of a typosquat domain. Typosquatting involves registering new domains with intentional misspelling designed to convince users to visit fake, and often malicious, websites. This technique is often used in phishing campaigns to create a sense of legitimacy and trust and deceive users into providing sensitive information. In this case, the suspicious domain closely resembled several of the customer’s internal domains, indicating an attempt to impersonate the organization’s legitimate internal sites to gain the target’s trust. Furthermore, the creation of this lookalike domain suggests that the attack was highly targeted at this specific customer.

Interestingly, the threat actor registered this spoofed domain despite already having account access. This was likely intended to ensure persistence on the network without having to launch additional phishing attacks. Such use of spoofed domain could allow an attacker to maintain a foothold in their target network and escalate their malicious activities without having to regain access to the account. This persistence can be used for various purposes, including data exfiltration, spreading malware, or launching further attacks.

Following this, Darktrace detected a highly anomalous email being sent to the customer’s account from the same location as the initial unusual SaaS login. Darktrace’s anomaly-based detection is able to identify threats that human security teams and traditional signature-based methods might miss. By analyzing the expected behavior of network users, Darktrace can recognize the subtle deviations from the norm that may indicate malicious activity. Unfortunately, in this instance, without Darktrace’s Autonomous Response capability enabled, the phishing email was able to successfully reach the recipient. While Darktrace / EMAIL did suggest that the email should be held from the recipients inbox, the customer was required to manually approve it.

Despite this, the Darktrace SOC team were still able to support the customer as they were subscribed to the Managed Threat Detection service. Following the detection of the highlight anomalous activity surrounding this compromise, namely the unusual SaaS login followed by a new email rule, an alert was sent to the Darktrace SOC for immediate triage, who then contacted the customer directly urging immediate action.

Conclusion

This case underscores the need to secure SaaS platforms like Microsoft 365 against sophisticated cyber threats. As businesses increasingly rely on these platforms, they become prime targets for attackers seeking unauthorized access and disruption.

Darktrace’s anomaly-based detection and response capabilities are crucial in identifying and mitigating such threats. In this instance, Darktrace detected a phishing email that led to a threat actor logging in and creating a suspicious email rule. The actor also registered a spoofed domain to maintain persistence on the network.

Darktrace / EMAIL, with its AI-driven detection and analysis, can block suspicious emails before they reach the intended recipient, preventing attacks at their inception. Meanwhile, Darktrace’s SOC team promptly investigated the activity and alerted the customer to the compromise, enabling them to take immediate action to remediate the issue and prevent any further damage.

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

Appendices

Darktrace Model Detections

  • SaaS / Access / Unusual External Source for SaaS Credential Use
  • SaaS / Compromise / Login From Rare Endpoint While User Is Active
  • SaaS / Resource / Unusual Access to Delegated Resource by Non Owner
  • SaaS / Email Nexus / Unusual Login Location Following Sender Spoof
  • Compliance / Anomalous New Email Rule
  • SaaS / Compromise / Unusual Login and New Email Rule

Indicators of Compromise (IoCs)

IoC - Type - Description + Confidence

31.222.254[.]27 – IP -  Suspicious Login Endpoint

MITRE ATT&CK Mapping

Tactic – Technqiue – Sub-technique of (if applicable)

Cloud Accounts - DEFENSE EVASION, PERSISTENCE, PRIVILEGE ESCALATION, INITIAL ACCESS - T1078.004 - T1078

Cloud Service Dashboard – DISCOVERY - T1538

Compromise Accounts - RESOURCE DEVELOPMENT - T1586

Steal Web Session Cookie - CREDENTIAL ACCESS - T1539

Outlook Rules – PERSISTENCE - T1137.005 - T1137

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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Vivek Rajan
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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