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April 10, 2023

Detecting Malicious Email Activity & AI Impersonating

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

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.
Written by
Isabelle Cheong
Cyber Security Analyst

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Email

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March 24, 2026

Darktrace Unites Human Behavior and Threat Detection Across Email, Slack, Teams, and Zoom

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The communication attack surface is expanding

Modern attackers no longer focus solely on inboxes, they target people and the productivity systems where work actually happens. Meanwhile, the boundary between internal and external usage of tools is becoming blurrier everyday – turning the entire workplace into the attack surface. In 2025, identity compromise emerged as the single most consistent threat across the global threat landscape, as observed by Darktrace research across our entire customer base. Over 70% of incidents in the US involved SaaS/M365 account compromise and phishing or email-based social engineering, making credential abuse the single most effective initial access vector.

Despite this upward trend, investment in existing security awareness training (SAT) isn’t moving the needle on reducing risk. 84% of organizations still measure success through completion rates1, even though completion of standard training correlates with less than 2% real improvement in risky behavior.2 By prioritizing completion, organizations reward time spent rather than meaningful engagement, yet time in training doesn’t translate to retention or real-world decision-making. This compliance-first approach has left the workforce unprepared for the threats they actually face.

At the same time, attacks have evolved. Highly personalized, AI-generated campaigns now move fluidly across email, Slack, Teams, Zoom, and beyond, blending channels and even targeting systems directly through techniques like prompt injection. This new reality demands a different approach: one that treats people and the tools they use as a single ecosystem, where behavior and detection continuously inform and strengthen each other.

Only an adaptive communication security system can keep pace with the speed, creativity, and cross channel nature of today’s threats. 

Ushering in the adaptive era of workplace security

With this release, Darktrace brings together our new behavior-driven training solution with email detection, cross-channel visibility, and platform-level insights. Powered by Self-Learning AI, it delivers protection across both people and the communication tools they rely on every day, including email, Slack, Teams, and Zoom.

Each component learns from the others – training adapts to real user behavior, detection evolves across channels, and response is continuously refined – creating a powerful feedback loop that strengthens resilience and improves accuracy against today’s AI-driven threats.

Introducing: Unified training and email security for a self-improving email defense

Our brand new product, Darktrace / Adaptive Human Defense, closes the gap between human behavior and email security to continuously strengthen both people and defenses. Each user receives personalized training that adapts to their own inbox activity and skill level, with learning delivered directly within the flow of their day-to-day email interactions.

By learning from each user’s interactions with security training, it adapts security responses, creating a closed-loop system where training reinforces detection and detection informs training. Let’s look at some of the benefits.

  • Reduce successful phishing at the source with contextual Just in Time coaching: Contextual coaching appears directly in real email threads the moment risky behavior is detected, so habits change where mistakes actually happen. Configurable triggers and group policies target the right users, reducing repeated errors and administrative overhead.
  • Adaptive phishing simulations that progress automatically with each user: Embedded simulations vary in their degree of realism, from generic phishing to generative AI-enabled spear phishing. Users progress through the difficulty levels based on their performance to give an accurate picture of their phishing preparedness.  
  • Native email security integration turns human behavior into quantified risk: The native email security integration allows engagement, links clicked, and question success signals to flow back into / EMAIL recipes and models, so detection and response adapt automatically as users learn.  
  • Actionable risk and trend analytics beyond completion rates: Analytics that surface repeat offenders, high-value targets, and measurable exposure, moving beyond completion metrics to give leaders actionable insights tied to real behavior.

Learn more about / Adaptive Human Defense in the product solution brief.

Industry-first cross-channel full-message analysis for email, Slack, Teams, and Zoom

Darktrace now brings full-message analysis to Email, Slack, Teams, Zoom, and even generative AI prompts. The same leading behavioral analysis from EMAIL extends to every message, tracing intent, tone, relationships, and conversation flow across all communication activity for a complete understanding of every user interaction.

By correlating messaging and collaboration activity with email and account environments, cross-channel analysis reveals multi-domain attack paths and follows both users and threats as a single, continuous narrative – delivering better context to improve detection across the entire organization.

  • Eliminate cross-channel blind spots: Detect phishing, malware, account takeovers, and conversational manipulation across email and collaboration platforms, so attackers can’t exploit Slack, Teams, or Zoom as a new entry point. Unified behavioral analysis gives security teams a coherent, single view, for no more fragmented, channel-specific gaps.
  • Spot generative AI prompt injection attacks before they manipulate assistants: Dedicated models surface threats targeting corporate AI assistants – like ShadowLeak and Hashjack – before they can silently manipulate workflows, reducing risk before static filters catch up.

Learn more about Darktrace’s messaging security offering in the product solution brief.

Industry-first DMARC with bi-directional ASM and email security integration

Darktrace transforms domain protection by linking DMARC, attack surface intelligence, and email security into a single, continuously evolving workflow. Instead of treating domain authentication and exposure as separate tasks, this unified approach shows not just where domains are vulnerable, but how attackers are actively exploiting them.

  • Fix authentication weaknesses faster: SPF, DKIM, DMARC configurations, and external exposure data are analyzed together, giving teams clear guidance to correct weaknesses before they can be abused. Deep bidirectional integration with attack surface intelligence reduces impersonation risk at the source.
  • Accelerate email investigations: DMARC context is embedded directly into email workflows, enriching triage with authentication posture, internal/external sender lists, and seamless pivots between email and domain intelligence for faster, more accurate investigations.

Committed to innovation

These updates are part of a broader Darktrace release, which also includes:

Join our Live Launch Event on April 14, 2026.

Join us for an exclusive announcement event where Darktrace, the leader in AI-native cybersecurity, will be announcing our latest innovations, including  a demo of our new product / Adaptive Human Defense, an exclusive conversation with a Darktrace customer, and a deep dive into the Darktrace ActiveAI Security Portal.  

Register here.

References

[1] 84% of organizations still measure security awareness training success through completion rates, a vanity metric with no correlation to behavior change. (Source:  NIST Awareness Effectiveness Study, Forrester 2025)

[2] 'Limited benefit from embedded phishing training. Using randomized controlled trials and statistical modeling, embedded training provides a statistically-significant reduction in average failure rate, but of only 2%.' Ho, G., Mirian, A., Luo, E., Tong, K., Lee, E., Liu, L., Longhurst, C. A., Dameff, C., Savage, S., & Voelker, G. M. (2025). Understanding the Efficacy of Phishing Training in Practice. Proceedings of the 2025 IEEE Symposium on Security and Privacy.

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About the author
Carlos Gray
Senior Product Marketing Manager, Email

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OT

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March 25, 2026

Advancing OT Security with Architecture Visibility, Operational Reporting, and Industrial Context

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The challenge of operational understanding in complex OT environments

Most industrial organizations today already have some level of asset visibility. The bigger challenge is maintaining a trusted, shared understanding of the environment as it evolves. OT teams still frequently rely on static diagrams, spreadsheets, and manually maintained documentation because these are often the only artifacts trusted by auditors, leadership, and engineering teams. However, these references quickly become outdated as environments change.

At the same time, compliance expectations continue to increase, particularly around IEC-62443 aligned programs. Producing defensible security evidence often requires teams to manually assemble reports across multiple tools while still debating asset inventories and classifications. This creates operational overhead and reduces confidence during audits, risk reviews, and incident response situations.

Advancing operational OT security with Darktrace / OT

Darktrace / OT's latest updates focus on helping industrial organizations close this operational gap by strengthening how OT security platforms support real workflows. This release enhances Operational Overview with architecture visibility, improves how industrial assets are represented, and introduces structured reporting capabilities aligned to governance needs.

Together, these improvements help organizations maintain a more reliable operational picture of their environments while reducing manual effort associated with documentation, reporting, and asset validation.

Native OT architecture visibility inside Operational Overview

Understanding how industrial environments are structured is critical during investigations and risk reviews, yet architecture diagrams are typically maintained outside security platforms and quickly fall out of sync with operational changes. This disconnect makes it harder for OT, IT, and security teams to maintain a shared understanding of their environments when incidents occur.

Darktrace / OT introduces native OT architecture diagrams directly within Operational Overview, allowing teams to maintain a live representation of how OT assets and systems relate to each other inside the same platform used for monitoring and investigations.

These updates help organizations:

  • Maintain a shared architectural understanding across OT, IT, and security teams
  • Improve investigation context by understanding how systems relate operationally
  • Reduce reliance on static diagrams that quickly become outdated

Improving OT governance with operational asset and compliance reporting

Accurate reporting remains a major operational challenge for industrial organizations, particularly when security posture must be demonstrated to auditors, regulators, and leadership. Many OT teams still rely on manual screenshots, spreadsheets, or fragmented exports to show asset inventories and compliance alignment.

Darktrace / OT introduces structured OT asset reporting and IEC-62443-3-3 compliance reporting directly from Operational Overview. These capabilities allow organizations to generate consistent, repeatable outputs based on continuously observed OT environments rather than manually assembled documentation.

These updates help customers:

  • Reduce manual compliance effort through automated IEC-62443 reporting aligned to live OT data
  • Support governance workflows with structured OT asset and architecture reporting
  • Improve audit readiness with consistent reporting aligned to operational security posture

Expanding industrial context through improved asset representation and protocol coverage

Industrial environments rely on diverse technologies spanning manufacturing systems, power and utilities infrastructure, healthcare devices, and Industrial IoT deployments. Maintaining strong visibility across these environments requires both accurate device representation and deeper protocol understanding.

Darktrace / OT strengthens industrial context through expanded ICS and IoMT device classification alongside broader industrial protocol coverage. These improvements help organizations better understand specialized devices and communications across sectors such as manufacturing, energy, healthcare, and Industrial IoT.

These enhancements enable organizations to:

  • Improve visibility into specialized ICS, IoMT, and industrial infrastructure devices
  • Strengthen monitoring across sector-specific industrial communications in manufacturing, utilities, and IIoT environments
  • Increase confidence in detection across complex and evolving industrial technology estates

Supporting practical OT security outcomes for industrial organizations

Darktrace / OT continues our focus on delivering capabilities that help industrial organizations operationalize security rather than simply deploy tools. By improving architecture understanding, strengthening asset representation, and supporting governance reporting, this release helps organizations manage OT security with greater confidence.

As industrial environments continue to evolve, organizations need more than visibility. They need the ability to maintain trusted operational understanding and demonstrate security readiness without increasing operational friction. This release reflects Darktrace’s continued commitment to supporting the priorities that matter most in OT: safety, uptime, and resilience.

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About the author
Pallavi Singh
Product Marketing Manager, OT Security & Compliance
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