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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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December 3, 2025

Darktrace Named as a Leader in 2025 Gartner® Magic Quadrant™ for Email Security Platforms

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Darktrace is proud to be named as a Leader in the Gartner® Magic Quadrant™ for Email Security Platforms (ESP). We believe this recognition reflects what our customers already know: our product is exceptional – and so is the way we deliver it.

In July 2025, Darktrace was named a Customers’ Choice in the Gartner® Peer Insights™ Voice of the Customer for Email Security, a distinction given to vendors who have scores that meet or exceed the market average for both axes (User Interest and Adoption, and Overall Experience). To us, both achievements are testament to the customer-first approach that has fueled our rapid growth. We feel this new distinction from Gartner validates the innovation, efficacy, and customer-centric delivery that set Darktrace apart.

A Gartner Magic Quadrant is a culmination of research in a specific market, giving you a wide-angle view of the relative positions of the market’s competitors. CIOs and CISOs can use this research to make informed decisions about which email security platform can best accomplish their goals. We encourage our customers to read the full report to get the complete picture.

This acknowledgement follows the recent recognition of Darktrace / NETWORK, also designated a Leader in the Gartner Magic Quadrant for Network Detection & Response and named the only Customers’ Choice in its category.

Why do we believe Darktrace is leading in the email security market?

Our relentless innovation which drives proven results  

At Darktrace we continue to push the frontier of email security, with industry-first AI-native detection and response capabilities that go beyond traditional SEG approaches. How do we do it?

  • With a proven approach that gets results. Darktrace’s unique business-centric anomaly detection catches advanced phishing, supply chain compromises, and BEC attacks – detecting them on average 13 days earlier than attack-centric solutions. That’s why 75% of our customers have removed their SEG and now rely on their native email security provider combined with Darktrace.
  • By offering comprehensive protection beyond the inbox. Darktrace / EMAIL goes further than traditional inbound filtering, delivering account and messaging protection, DLP, and DMARC capabilities, ensuring best-in-class security across inbound, outbound, and domain protection scenarios.  
  • Continuous innovation. We are ranked second highest in the Gartner Critical Capabilities research for core email security function, likely thanks to our product strategy and rapid pace of innovation. We’ve release major capabilities twice a year for nearly five years, including advanced AI models and expanded coverage for collaboration platforms.

We deliver exceptional customer experiences worldwide

Darktrace’s leadership isn’t just about excelling in technology, it’s about delivering an outstanding experience that customers value. Let’s dig into what makes our customers tick.

  • Proven loyalty from our base. Recognition from Gartner Peer Insights as a Customers’ Choice, combined with a 4.8-star rating (based on 340 reviews as of November 2025), demonstrates for us the trust of thousands of organizations worldwide, not just the analysts.  
  • Customer-first support. Darktrace goes beyond ticket-only models with dedicated account teams and award-winning service, backed by significant headcount growth in technical support and analytics roles over the past year.
  • Local expertise. With offices spanning continents, Darktrace is able to provide regional language support and tailored engagement from teams on the ground, ensuring personalized service and a human-first experience.

Darktrace enhances security stacks with a partner-first architecture

There are plenty of tools out there than encourage a siloed approach. Darktrace / EMAIL plays well with others, enhancing your native security provider and allowing you to slim down your stack. It’s designed to set you up for future growth, with:

  • A best-in-breed platform approach. Natively built on Self-Learning AI, Darktrace / EMAIL delivers deep integration with our / NETWORK, / IDENTITY, and / CLOUD products as part of a unified platforms – that enables and enhances comprehensive enterprise-wise security.
  • Optimized workflows. Darktrace integrates tightly with an extended ecosystem of security tools – including a strategic partnership with Microsoft enabling unified threat response and quarantine capabilities – bringing constant innovation to all of your SOC workflows.  
  • A channel-first strategy. Darktrace is making significant investments in partner-driven architectures, enabling integrated ecosystems that deliver maximum value and future-ready security for our customers.

Analyst recognized. Customer approved.  

Darktrace / EMAIL is not just another inbound email security tool; it’s an advanced email security platform trusted by thousands of users to protect them against advanced phishing, messaging, and account-level attacks.  

As a Leader, we believe we owe our positioning to our customers and partners for supporting our growth. In the upcoming years we will continue to innovate to serve the organizations who depend on Darktrace for threat protection.  

To learn more about Darktrace’s position as a Leader, view a complimentary copy of the Magic Quadrant report, register for the Darktrace Innovation Webinar on 9 December, 2025, or simply request a demo.

Gartner, Gartner® Magic Quadrant™ for Email Security Platforms, Max Taggett, Nikul Patel, 3 December 2025

GARTNER is a registered trademark and service mark of Gartner, Inc. and/or its affiliates in the U.S. and internationally and is used herein with permission. All rights reserved. Magic Quadrant is a registered trademark of Gartner, Inc. and/or its affiliates and is used herein with permission. All rights reserved.

Gartner does not endorse any vendor, product or service depicted in its research publications, and does not advise technology users to select only those vendors with the highest ratings or other designation. Gartner research publications consist of the opinions of Gartner’s research organization and should not be construed as statements of fact. Gartner disclaims all warranties, expressed or implied, with respect to this research, including any warranties of merchantability or fitness for a particular purpose.

This graphic was published by Gartner, Inc. as part of a larger research document and should be evaluated in the context of the entire document. The Gartner document is available upon request from Darktrace.

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About the author
Carlos Gray
Senior Product Marketing Manager, Email

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December 2, 2025

Protecting the Experience: How a global hospitality brand stays resilient with Darktrace

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For the Global Chief Technology Officer (CTO) of a leading experiential leisure provider, security is mission critical to protecting a business built on reputation, digital innovation, and guest experience. The company operates large-scale immersive venues across the UK and US, blending activity-driven hospitality with premium dining and vibrant spaces designed for hundreds of guests. With a lean, centrally managed IT team responsible for securing locations worldwide, the challenge is balancing robust cybersecurity with operational efficiency and customer experience.

Brand buzz attracts attention – and attacks

Mid-sized, fast-growing hospitality organizations face a unique risk profile. When systems go down in a venue, the impact is immediate: hundreds of disrupted guest experiences, lost revenue during peak hours, and potential long-term reputation damage. Each time the organization opened a new venue, the surge of marketing buzz attracted attention in local markets and waves of sophisticated cyberattacks, including:

Phishing campaigns leveraging brand momentum to lure employees into clicking on malicious links.

AI-enhanced impersonation using advanced techniques to create AI-generated video calls and deep-researched, contextualized emails  

Fake domains targeting leadership with AI-generated messages that contained insider context gleaned from public information.

“Our endpoint security and antivirus tools were powerless against these sophisticated AI-powered campaigns. We didn’t want to manage incidents anymore. We wanted to prevent them from ever happening.”  - Global CTO

Proactive, preventative security with Darktrace AI

The company’s cybersecurity vision was clear: “Proactive, preventative – that was our mandate,” said the CTO. With a lean and busy IT group, the business evaluated several security solutions using deep-dive workshops. Darktrace proved the best fit for supporting the organization’s proactive mindset, offering:

  • Autonomy without added headcount: Darktrace provided powerful AI-driven detection and autonomous response functions with minimal manual oversight required.
  • Modular adoption: The company could start with core email and network protection and expand into cloud and endpoint coverage, aligning spend with growth.
  • Partnership and responsiveness: “We wanted people we trust, respect, and know will show up when we need them. Darktrace did just that,” said the CTO.
  • Affordability at scale: Darktrace offered reasonable upfront costs plus predictable, sustainable economics as the company and IT infrastructure expanded.  

“The combination of AI capabilities, a scalable model, and a strong engagement team tipped the balance in Darktrace’s favor, and we have not been disappointed,” said the CTO.

Phased deployment builds trust

To minimize disruption to critical hospitality systems like global Point of Sales (POS) terminals and Audio-Visual (AV) infrastructure, deployment was phased:

  1. Observation and human-led response: Initially, Darktrace was deployed in detection-only mode. Alerts were manually reviewed.
  2. Incremental autonomous response: Darktrace Autonomous Response was enabled on select models, taking action on low-risk scenarios. Higher-risk subnets and devices remained under human control.
  3. Full autonomous coverage: With tuning and reinforcement, autonomous response was expanded across domains, trusted to take decisive action in real time. Analysts retained the ability to review and contextualize incidents.

“Darktrace managed the rollout through detailed, professional, and responsive project management – ensuring a smooth, successful adoption and creating a standardized cybersecurity playbook for future venue launches,” said the CTO.  

AI delivers the outcomes that matter  

Measurable efficiency replaces endless alerts

Darktrace autonomous response significantly decreased false alerts and noise. “If it’s quiet, we’re confident there isn’t a problem,” said the CTO. Within six months, Darktrace conducted 3,599 total investigations, detected and contained 320 incidents indicative of an attack, resolved 91% of those events autonomously, and escalated only 9% to human analysts. The efficiency gains were enormous, saving analysts 740 hours on investigations within a single month.  

Precision AI turns inbox chaos into calm

Darktrace Self-Learning AI modeled sender/recipient norms, content/linguistic baselines, and communication patterns unique to the organization’s launch cadence, resulting in:

  • Automated holds and neutralizations of anomalous executive-style messages
  • Rapid detection of novel templates and tone shifts that deviated from the organization’s lived email graph, even when indicators were not yet on any feed
  • Downstream reduction in help-desk escalations tied to suspicious email

Full visibility fuels real-time response

Darktrace gives IT direct visibility without extra licensing, and it surfaces ground truth across every venue, including:

  • Device geolocation and placement drift: Darktrace exposed devices and users operating outside approved zones, prompting new segmentation and access-control policies.
  • Guest Wi-Fi realities: Darktrace AI uncovered high-risk activity on guest networks, like crypto-mining and dark-web traffic, driving stricter VLAN separation and access hygiene.
  • Lateral-movement containment: Autonomous response fenced suspicious activity in real time, buying time for human investigation while keeping POS and AV systems unaffected.

Smarter endpoints for a smarter network

Endpoints once relied on static agents effective only against known signatures. Darktrace’s behavioral models now detect subtle anomalies at the endpoint process level that EDRs often miss, such as misuse of legitimate applications (commonly used in living-off-the-land attacks), unapproved application usage and policy violations. This increases the accuracy and fidelity of network-based investigations by adding endpoint process context alongside existing EDR alerts.

Autonomous response for continuous compliance

Across PCI, GDPR, and cross-border privacy obligations, Darktrace’s native evidencing is helping the team demonstrate control rather than merely assert it:

  • Asset and flow awareness: Knowing “what is where” and “who talks to what” underpins PCI scoping and data-flow diagrams.
  • Layered safeguards: Showing autonomous prevention, network segmentation, and rapid containment supports risk registers and control attestations.
  • Audit-ready artifacts: Investigations and autonomous actions produce artifacts that “tick the box” without additional tooling.  

Defining the next era of resilience with AI

With rapid global expansion underway, the company is using its cybersecurity playbook to streamline and secure future venue launches. In the near term, IT is focused on strengthening prevention, using Darktrace insights to guide new policy updates and infrastructure changes like imposing stricter guest-network posture and refining venue device baselines.

For tech leaders charting their path to proactive cyber defense, the CTO stresses success won’t come from sidestepping AI, but from turning it into a core capability.

“AI isn’t optional – it’s operational. The real risk to your business is trying to out-scale automated adversaries with human speed alone. When applied to the right use case, AI becomes a catalyst for efficiency, resilience, and business growth.” - Global CTO
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