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April 10, 2023

Detecting Malicious Email Activity & AI Impersonating

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10
Apr 2023
Discover how two different phishing attempts from some known and unknown senders used a payroll diversion and credential sealing box link to harm users.

Social engineering has become widespread in the cyber threat landscape in recent years, and the near-universal use of social media today has allowed attackers to research and target victims more effectively. Social engineering involves manipulating users to carry out actions such as revealing sensitive information like login credentials or credit card details. It can also lead to user account compromises, causing huge disruption to an organization’s digital estate. 

As people use social media platforms not only for personal reasons, but also for business purposes, attackers gain information they can exploit in social engineering attacks. For example, a threat actor may attempt to impersonate a known individual or legitimate service to take advantage of a user’s established trust. This is a highly successful method of social engineering because mimicking known contacts makes it difficult for traditional security tools that rely on deny-lists to detect the attack.

In October 2022, Darktrace identified and responded to two separate malicious email campaigns in which threat actors attempted to impersonate known contacts in an effort to compromise customer devices. As it learns the normal behavior of every user in the email system, Darktrace was able to instantly detect these threats and mitigate them autonomously, preventing significant disruption to the customer networks.

Payroll Diversion Fraud Attempt Impersonating a Former Employee 

While a customer in the Canadian energy sector was trialing Darktrace in October 2022, Darktrace/Email™ identified a suspicious email seemingly sent from an employee within the organization. The email was sent to the Senior Director of Human Resources (HR) with a subject line of “Change in payroll Direct Deposit.” The email requested a change in bank account information for an employee. However, Darktrace recognized that the sender was using a free mail address that contained random letters, indicating it may have been algorithmically generated. Since this incident occurred during a trial, Darktrace/Email was not configured to take action. Otherwise, it would have prevented the email from landing in the inbox. In this case though, the email went through, bypassing all other security tools in place.

Although the email was from an unknown sender, the HR director believed the email could have been legitimate as the employee who appeared to be the sender had left the organization seven days prior and no longer had access to their corporate email account. However, after reviewing it in the Darktrace/Email dashboard, the customer grew suspicious and contacted the former employee directly to verify if the request was legitimate. The former employee validated the suspicions by confirming they had sent no such email.

Further investigation by the customer revealed that the former employee had been vocal about their departure on various social media platforms. This gave threat actors valuable information to believably impersonate the former employee and defraud the organization. 

Such attempts to target organizations’ HR departments and divert payroll are common tactics for cyber-criminals and are often identified by Darktrace/Email across the customer base. Darktrace/Email is able to instantly identify the indicators associated with these spoofing attempts and immediately bring them to the attention of the customer’s security team. 

Using Legitimate File Sharing Service to Share a Phishing Link 

On October 7, 2022, a customer in the Singaporean construction sector was targeted by a phishing campaign attempting to impersonate a law firm known to the organization. Almost 200 employees received an email with the subject line “Accepted: Valuation Agreement.” 

Figure 1: Sample of an UI view of the message held showing anomaly indicators, history, association, and validation.

Four days earlier, Darktrace observed communication between another email address associated with the law firm and an employee of the customer. Darktrace/Email noted that it was the first time this correspondent had sent emails to the customer. 

Figure 2: Metrics showing how well the sender’s domain is known within the digital environment.

The emails contained a highly unusual link to a file sharing service, (hxxps://ssvilvensstokes[.]app[.]box[.]com/notes), hidden behind the text “PREVIEW OR PRINT COPY OF DOCUMENT HERE.” Darktrace analysts investigated this event further and found that around 30 similar URLs had been identified as suspicious using OSINT security tools in October 2022, suggesting the customer was not the only target of this phishing campaign.

Figure 3: Preview of the phishing email’s body.
Figure 4: Darktrace’s evaluation of the link contained in the phishing email.

Additional OSINT work revealed that the link directed to a website which appeared to host a PDF file named “Valuation Agreement.” The recipient would then be prompted to follow another link (hulking-citrine-krypton[.]glitch[.]me), again hidden behind the text “OPEN OR ACCESS DOCUMENT HERE” to view the file. Subsequently, the user would be prompted to enter their Microsoft 365 credentials. 

Figure 5: The page displayed when the phishing link was clicked, viewed in a sandbox environment.
Figure 6: Example of a page shown when recipient clicks the second link, accessing “hulking-citrine-krypton[.]glitch[.]me”. 

This page contained the text “This document has been scanned for viruses by Norton Antivirus Security.” This is another example of threat actors’ employing social engineering techniques by impersonating well-known brands, such as established security vendors, to gain the trust of users and increase their likelihood of success.

It is highly probable that a real employee of the law firm had their account hijacked and that a malicious actor was exploiting it to send out these phishing emails en masse as part of a supply chain attack. In such cases, malicious actors rely on their targets’ trust of known contacts to not question departures from their normal conversations. 

Darktrace was able to instantly detect multiple anomalies in these emails, despite the fact that they were seemingly sent by known correspondents. The activity detected automatically triggered model breaches associated with unexpected and visually prominent links. As a result, Darktrace/Email responded by locking the link, stopping users from being able to click it.

Darktrace subsequently identified additional emails from this sender attempting to target other recipients within the company, triggering the model breaches associated with a surge in email sending indicative of a phishing campaign. In response, Darktrace/Email autonomously acted and filed these emails as junk. As more emails were detected across the customer’s environment, the anomaly score of the sender increased and Darktrace ultimately held back over 160 malicious emails, safeguarding recipients from potential account compromise.           

The following Darktrace/Email models were breached throughout the course of this phishing campaign:

  • Unusual/Sender Surge 
  • Unusual/Undisclosed Recipients 
  • Antigena Anomaly 
  • Association/Unlikely Recipient Association 
  • Link/Low Link Association 
  • Link/Visually Prominent Link 
  • Link/Visually Prominent Link Unexpected For Sender 
  • Unusual/New Sender Wide Distribution
  • Unusual/Undisclosed Recipients + New Address Known Domain

Conclusion

Social engineering plays a role in many of the major threats challenging current email cyber security, as attackers can use it to manipulate users into transferring money, revealing credentials, clicking malicious links, and more. 

The above threat stories happened before language generating AI became mainstream with the release of ChatGPT in December 2022. Now, it is even easier for malicious actors to generate sophisticated social engineering emails. By using social media posts as input, social engineering emails written by generative AI can be highly targeted and produced at scale. They often avoid the flags users are trained to look for, like poor grammar and spelling mistakes, and can hide payloads or forgo them entirely.

To mitigate the risk of possible social engineering attempts, it is recommended that organizations implement social media policies that advise employees to be cautious of what they post online and enact procedures to verify if fund transfer requests are legitimate.

Yet these policies are not enough on their own. Darktrace/Email can identify suspicious email traits, whether an email is sent from a known correspondent or an unknown sender. With Self-Learning AI, it knows an organization’s users better than any impersonator could. In this way, Darktrace/Email detects anomalies within emails and neutralizes malicious components at machine-speed, stopping attacks at their earliest stages, before employees fall victim. 

Appendices

List of Indicators of Compromise (IoCs)

Domain:

hxxps://ssvilvensstokes[.]app[.]box[.]com/notes/*?s=* - 1st external link (seen in email)

hxxps://hulking-citrine-krypton[.]glitch[.]me/flk.html - 2nd external link, masked behind “OPEN OR ACCESS DOCUMENT HERE”

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.
Author
Isabelle Cheong
Cyber Security Analyst
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February 19, 2025

Darktrace Releases Annual 2024 Threat Insights

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Introduction: Darktrace’s threat research

Defenders must understand the threat landscape in order to protect against it. They can do that with threat intelligence.

Darktrace approaches threat intelligence with a unique perspective. Unlike traditional security vendors that rely on established patterns from past incidents, it uses a strategy that is rooted in the belief that identifying behavioral anomalies is crucial for identifying both known and novel threats.

For Darktrace analysts and researchers, the incidents detected by the AI solution mark the beginning of a deeper investigation, aiming to connect mitigated threats to wider trends from across the threat landscape. Through hindsight analysis, the Darktrace Threat Research team has highlighted numerous threats, including zero-day, n-day, and other novel attacks, showcasing their evolving nature and Darktrace’s ability to identify them.

In 2024, the Threat Research team observed major trends around vulnerabilities in internet-facing systems, new and re-emerging ransomware strains, and sophisticated email attacks. Read on to discover some of our key insights into the current cybersecurity threat landscape.

Multiple campaigns target vulnerabilities in internet-facing systems

It is increasingly common for threat actors to identify and exploit newly discovered vulnerabilities in widely used services and applications, and in some cases, these vulnerability exploitations occur within hours of disclosure.

In 2024, the most significant campaigns observed involved the ongoing exploitation of zero-day and n-day vulnerabilities in edge and perimeter network technologies. In fact, in the first half of the year, 40% of all identified campaign activity came from the exploitation of internet-facing devices. Some of the most common exploitations involved Ivanti Connect Secure (CS) and Ivanti Policy Secure (PS) appliances, Palo Alto Network (PAN-OS) firewall devices, and Fortinet appliances.

Darktrace helps security teams identify suspicious behavior quickly, as demonstrated with the critical vulnerability in PAN-OS firewall devices. The vulnerability was publicly disclosed on April 11, 2024, yet with anomaly-based detection, Darktrace’s Threat Research team was able to identify a range of suspicious behavior related to exploitation of this vulnerability, including command-and-control (C2) connectivity, data exfiltration, and brute-forcing activity, as early as March 26.

That means that Darktrace and our Threat Research team detected this Common Vulnerabilities and Exposure (CVE) exploitation 16 days before the vulnerability was disclosed. Addressing critical vulnerabilities quickly massively benefits security, as teams can reduce their effectiveness by slowing malicious operations and forcing attackers to pursue more costly and time-consuming methods.

Persistent ransomware threats continue to evolve

The continued adoption of the Ransomware-as-a-Service (RaaS) model provides even less experienced threat actors with the tools needed to carry out disruptive attacks, significantly lowering the barrier to entry.

The Threat Research team tracked both novel and re-emerging strains of ransomware across the customer fleet, including Akira, LockBit, and Lynx. Within these ransomware attempts and incidents, there were notable trends in attackers’ techniques: using phishing emails as an attack vector, exploiting legitimate tools to mask C2 communication, and exfiltrating data to cloud storage services.

Read the Annual 2024 Threat Report for the complete list of prominent ransomware actors and their commonly used techniques.

Onslaught of email threats continues

With a majority of attacks originating from email, it is crucial that organizations secure the inboxes and beyond.

Between December 21, 2023, and December 18, 2024, Darktrace / EMAIL detected over 30.4 million phishing emails across the fleet. Of these, 70% successfully bypassed Domain-based Message Authentication, Reporting, and Conformance (DMARC) verification checks and 55% passed through all other existing layers of customer email security.

The abuse of legitimate services and senders continued to be a significant method for threat actors throughout 2024. By leveraging trusted platforms and domains, malicious actors can bypass traditional security measures and increase the likelihood of their phishing attempts being successful.

This past year, there was a substantial use of legitimately authenticated senders and previously established domains, with 96% of phishing emails detected by Darktrace / EMAIL utilizing existing domains rather than registering new ones.

These are not the only types of email attacks we observed. Darktrace detected over 2.7 million emails with multistage payloads.

While most traditional cybersecurity solutions struggle to cover multiple vectors and recognize each stage of complex attacks as part of wider malicious activity, Darktrace can detect and respond across email, identities, network, and cloud.

Conclusion

The Darktrace Threat Research team continues to monitor the ever-evolving threat landscape. Major patterns over the last year have revealed the importance of fast-acting, anomaly-based detection like Darktrace provides.

For example, response speed is essential when campaigns target vulnerabilities in internet-facing systems, and these vulnerabilities can be exploited by attackers within hours of their disclosure if not even before that.

Similarly, anomaly-based detection can identify hard to find threats like ransomware attacks that increasingly use living-off-the-land techniques and legitimate tools to hide malicious activity. A similar pattern can be found in the realm of email security, where attacks are also getting harder to spot, especially as they frequently exploit trusted senders, use redirects via legitimate services, and craft attacks that bypass DMARC and other layers of email security.

As attacks appear with greater complexity, speed, and camouflage, defenders must have timely detection and containment capabilities to handle all emerging threats. These hard-to-spot attacks can be identified and stopped by Darktrace.

Download the full report

Discover the latest threat landscape trends and recommendations from the Darktrace Threat Research team.

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The Darktrace Threat Research Team

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February 18, 2025

Unifying IT & OT With AI-Led Investigations for Industrial Security

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As industrial environments modernize, IT and OT networks are converging to improve efficiency, but this connectivity also creates new attack paths. Previously isolated OT systems are now linked to IT and cloud assets, making them more accessible to attackers.

While organizations have traditionally relied on air gaps, firewalls, data diodes, and access controls to separate IT and OT, these measures alone aren’t enough. Threat actors often infiltrate IT/Enterprise networks first then exploit segmentation, compromising credentials, or shared IT/OT systems to move laterally, escalate privileges, and ultimately enter the OT network.

To defend against these threats, organizations must first ensure they have complete visibility across IT and OT environments.

Visibility: The first piece of the puzzle

Visibility is the foundation of effective industrial cybersecurity, but it’s only the first step. Without visibility across both IT and OT, security teams risk missing key alerts that indicate a threat targeting OT at their earliest stages.

For Attacks targeting OT, early stage exploits often originate in IT environments, adversaries perform internal reconnaissance among other tactics and procedures but then laterally move into OT first affecting IT devices, servers and workstations within the OT network. If visibility is limited, these threats go undetected. To stay ahead of attackers, organizations need full-spectrum visibility that connects IT and OT security, ensuring no early warning signs are missed.

However, visibility alone isn’t enough. More visibility also means more alerts, this doesn’t just make it harder to separate real threats from routine activity, but bogs down analysts who have to investigate all these alerts to determine their criticality.

Investigations: The real bottleneck

While visibility is essential, it also introduces a new challenge: Alert fatigue. Without the right tools, analysts are often occupied investigating alerts with little to no context, forcing them to manually piece together information and determine if an attack is unfolding. This slows response times and increases the risk of missing critical threats.

Figure 1: Example ICS attack scenario

With siloed visibility across IT and OT each of these events shown above would be individually alerted by a detection engine with little to no context nor correlation. Thus, an analyst would have to try to piece together these events manually. Traditional security tools struggle to keep pace with the sophistication of these threats, resulting in an alarming statistic: less than 10% of alerts are thoroughly vetted, leaving organizations vulnerable to undetected breaches. As a result, incidents inevitably follow.

Darktrace’s Cyber AI Analyst uses AI-led investigations to improve workflows for analysts by automatically correlating alerts wherever they occur across both IT and OT. The multi-layered AI engine identifies high-priority incidents, and provides analysts with clear, actionable insights, reducing noise and highlighting meaningful threats. The AI significantly alleviates workloads, enabling teams to respond faster and more effectively before an attack escalates.

Overcoming organizational challenges across IT and OT

Beyond technical challenges like visibility and alert management, organizational dynamics further complicate IT-OT security efforts. Fundamental differences in priorities, workflows, and risk perspectives create challenges that can lead to misalignment between teams:

Non-transferable practices: IT professionals might assume that cybersecurity practices from IT environments can be directly applied to OT environments. This can lead to issues, as OT systems and workflows may not handle IT security processes as expected. It's crucial to recognize and respect the unique requirements and constraints of OT environments.

Segmented responsibilities: IT and OT teams often operate under separate organizational structures, each with distinct priorities, goals, and workflows. While IT focuses on data security, network integrity, and enterprise applications, OT prioritizes uptime, reliability, and physical processes.

Different risk perspectives: While IT teams focus on preventing cyber threats and regulatory violations, OT teams prioritize uptime and operational reliability making them drawn towards asset inventory tools that provide no threat detection capability.

Result: A combination of disparate and ineffective tools and misaligned teams can make any progress toward risk reduction at an organization seem impossible. The right tools should be able to both free up time for collaboration and prompt better communication between IT and OT teams where it is needed. However, different size operations structure their IT and OT teams differently which impacts the priorities for each team.

In real-world scenarios, small IT teams struggle to manage security across both IT and OT, while larger organizations with OT security teams face alert fatigue and numerous false positives slowing down investigations and hindering effective communication with the IT security teams.

By unifying visibility and investigations, Darktrace / OT helps organizations of all sizes detect threats earlier, streamline workflows, and enhance security across both IT and OT environments. The following examples illustrate how AI-driven investigations can transform security operations, improving detection, investigation, and response.

Before and after AI-led investigation

Before: Small manufacturing company

At a small manufacturing company, a 1-3 person IT team juggles everything from email security to network troubleshooting. An analyst might see unusual traffic through the firewall:

  • Unusual repeated outbound traffic from an IP within their OT network destined to an unidentifiable external IP.

With no dedicated OT security tools and limited visibility into the industrial network, they don’t know what the internal device in question is, if it is beaconing to a malicious external IP, and what it may be doing to other devices within the OT network. Without a centralized dashboard, they must manually check logs, ask operators about changes, and hunt for anomalies across different systems.

After a day of investigation, they concluded the traffic was not to be expected activity. They stop production within their smaller OT network, update their firewall rules and factory reset all OT devices and systems within the blast radius of the IP device in question.

After: Faster, automated response with Cyber AI Analyst

With Darktrace / OT and Cyber AI Analyst, the IT team moves from reactive, manual investigations to proactive, automated threat detection:

  • Cyber AI Analyst connects alerts across their IT and OT infrastructure temporally mapping them to attack frameworks and provides contextual analysis of how alerts are linked, revealing in real time attackers attempting lateral movement from IT to OT.
  • A human-readable incident report explains the full scope of the incident, eliminating hours of manual investigation.
  • The team is faster to triage as they are led directly to prioritized high criticality alerts, now capable of responding immediately instead of wasting valuable time hunting for answers.

By reducing noise, providing context, and automating investigations, Cyber AI Analyst transforms OT security, enabling small IT teams to detect, understand, and respond to threats—without deep OT cybersecurity expertise.

Before: Large critical infrastructure organization

In large critical infrastructure operations, OT and IT teams work in separate silos. The OT security team needs to quickly assess and prioritize alerts, but their system floods them with notifications:

  • Multiple new device connected to the ICS network alerts
  • Multiple failed logins to HMI detected
  • Multiple Unusual Modbus/TCP commands detected
  • Repeated outbound OT traffic to IT destinations

At first glance, these alerts seem important, but without context, it’s unclear whether they indicate a routine error, a misconfiguration, or an active cyber-attack. They might ask:

  • Are the failed logins just a mistake, or a brute-force attempt?
  • Is the outbound traffic part of a scheduled update, or data exfiltration?

Without correlation across events, the engineer must manually investigate each one—checking logs, cross-referencing network activity, and contacting operators—wasting valuable time. Meanwhile, if it’s a coordinated attack, the adversary may already be disrupting operations.

After: A new workflow with Cyber AI Analyst

With Cyber AI Analyst, the OT security team gets clear, automated correlation of security events, making investigations faster and more efficient:

  • Automated correlation of OT threats: Instead of isolated alerts, Cyber AI Analyst stitches together related events, providing a single, high-confidence incident report that highlights key details.
  • Faster time to meaning: The system connects anomalous behaviors (e.g., failed logins, unusual traffic from an HMI, and unauthorized PLC modifications) into a cohesive narrative, eliminating hours of manual log analysis.
  • Prioritized and actionable alerts: OT security receives clear, ranked incidents, immediately highlighting what matters most.
  • Rapid threat understanding: Security teams know within minutes whether an event is a misconfiguration or a cyber-attack, allowing for faster containment.

With Cyber AI Analyst, large organizations cut through alert noise, accelerate investigations, and detect threats faster—without disrupting OT operations.

An AI-led approach to industrial cybersecurity

Security vendors with a primary focus on IT may lack insight into OT threats. Even OT-focused vendors have limited visibility into IT device exploitation within OT networks, leading to failed ability to detect early indicators of compromise. A comprehensive solution must account for the unique characteristics of various OT environments.

In a world where industrial security is no longer just about protecting OT but securing the entire digital-physical ecosystem as it interacts with the OT network, Darktrace / OT is an AI-driven solution that unifies visibility across IT, IoT and OT, Cloud into one cohesive defense strategy.

Whether an attack originates from an external breach, an insider threat, a supply chain compromise, in the Cloud, OT, or IT domains Cyber AI Analyst ensures that security teams see the full picture - before disruption occurs.

Learn more about Darktrace / OT 

  • Unify IT and OT security under a single platform, ensuring seamless communication and protection for all interconnected devices.
  • Maintain uptime with AI-driven threat containment, stopping attacks without disrupting production.
  • Mitigate risks with or without patches, leveraging MITRE mitigations to reduce attack opportunities.

Download the solution brief to see how Darktrace secures critical infrastructure.

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About the author
Daniel Simonds
Director of Operational Technology
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