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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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April 28, 2026

State of AI Cybersecurity 2026: 87% of security professionals are seeing more AI-driven threats, but few feel ready to stop them

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The findings in this blog are taken from Darktrace’s annual State of AI Cybersecurity Report 2026.

In part 1 of this blog series, we explored how AI is remaking the attack surface, with new tools, models, agents — and vulnerabilities — popping up just about everywhere. Now embedded in workflows across the enterprise, and often with far-reaching access to sensitive data, AI systems are quickly becoming a favorite target of cyber threat actors.

Among bad actors, though, AI is more often used as a tool than a target. Nearly 62% of organizations  experienced a social engineering attack involving a deepfake, or an incident in which bad actors used AI-generated video or audio to try to trick a biometric authentication system, compared to 32% that reported an AI prompt injection attack.

In the hands of attackers, AI can do many things. It’s being used across the entire kill chain: to supercharge reconnaissance, personalize phishing, accelerate lateral movement, and automate data exfiltration. Evidence from Anthropic demonstrates that threat actors have harnessed AI to orchestrate an entire cyber espionage campaign from end to end, allegedly running it with minimal human involvement.

CISOs inhabit a world where these increasingly sophisticated attacks are ubiquitous. Naturally, combatting AI-powered threats is top of mind among security professionals, but many worry about whether their capabilities are up to the challenge.

AI-powered threats at scale: no longer hypothetical

AI-driven threats share signature characteristics. They operate at speed and scale. Automated tools can probe multiple attack paths, search for multiple vulnerabilities and send out a barrage of phishing emails, all within seconds. The ability to attack everywhere at once, at a pace that no human operator could sustain, is the hallmark of an AI-powered threat. AI-powered threats are also dynamic. They can adapt their behavior to spread across a network more efficiently or rewrite their own code to evade detection.

Security teams are seeing the signs that they’re fighting AI-powered threats at every stage of the kill chain, and the sophistication of these threats is testing their resolve and their resources.

  • 73% say that AI-powered cyber threats are having a significant impact on their organization
  • 92% agree that these threats are forcing them to upgrade their defenses
  • 87% agree that AI is significantly increasing the sophistication and success rate of malware
  • 87% say AI is significantly increasing the workload of their security operations team

These teams now confront a challenge unlike anything they’ve seen before in their careers, and the risks are compounding across workflows, tools, data, and identities. It’s no surprise that 66% of security professionals say their role is more stressful today than it was five years ago, or that 47% report feeling overwhelmed at work.

Up all night: Security professionals’ worry list is long

Traditional security methods were never built to handle the complexity and subtlety of AI-driven behavior. Working in the trenches, defenders have deep firsthand experience of how difficult it can be to detect and stop AI-assisted threats.

Increasingly effective social engineering attacks are among their top concerns. 50% of security leaders mentioned hyper-personalized phishing campaigns as one of their biggest worries, while 40% voiced apprehension about deepfake voice fraud. These concerns are legitimate: AI-generated phishing emails are increasingly tailored to individual organizations, business activities, or individuals. Gone are the telltale signs – like grammar or spelling mistakes – that once distinguished malicious communications. Notably, 33% of the malicious emails Darktrace observed in 2025 contained over 1,000 characters, indicating probable LLM usage.

Security leaders also worry about how bad actors can leverage AI to make attacks even faster and more dynamic. 45% listed automated vulnerability scanning and exploit chaining among their biggest concerns, while 40% mentioned adaptive malware.

Confidence is lacking

Protecting against AI demands capabilities that many organizations have not yet built. It requires interpreting new indicators, uncovering the subtle intent within interactions, and recognizing when AI behavior – human or machine – could be suspicious. Leaders know that their current tools aren’t prepared for this. Nearly half don’t feel confident in their ability to defend against AI-powered attacks.

We’ve asked participants in our survey about their confidence for the last three years now. In 2024, 60% said their organizations were not adequately prepared to defend against AI-driven threats. Last year, that percentage shrunk to 45%, a possible indicator that security programs were making progress. Since then, however, the progress has apparently stalled. 46% of security leaders now feel inadequately prepared to protect their organizations amidst the current threat landscape.

Some of these differences are accentuated across different cultures. Respondents in Japan are far less confident (77% say they are not adequately prepared) than respondents in Brazil (where only 21% don’t feel prepared).

Where security programs are falling short

It’s no longer the case that cybersecurity is overlooked or underfunded by executive leadership. Across industries, management recognizes that AI-powered threats are a growing problem, and insufficient budget is near the bottom of most CISO’s list of reasons that they struggle to defend against AI-powered threats.  

It’s the things that money can’t buy – experience, knowledge, and confidence – that are holding programs back. Near the top of the list of inhibitors that survey participants mention is “insufficient knowledge or use of AI-driven countermeasures.” As bad actors embrace AI technologies en masse, this challenge is coming into clearer focus: attack-centric security tools, which rely on static rules, signatures, and historical attack patterns, were never designed to handle the complexity and subtlety of AI-driven attacks. These challenges feel new to security teams, but they are the core problems Darktrace was built to solve.  

Our Self-Learning AI develops a deep understanding of what “normal” looks like for your organization –including unique traffic patterns, end user habits, application and device profiles – so that it can detect and stop novel, dynamic threats at the first encounter. By focusing on learning the business, rather than the attack, our AI can keep pace with AI-powered threats as they evolve.

Explore the full State of AI Cybersecurity 2026 report for deeper insights into how security leaders are responding to AI-driven risks.

Learn more about securing AI in your enterprise.

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April 24, 2026

Email-Borne Cyber Risk: A Core Challenge for the CISO in the Age of Volume and Sophistication

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The challenge for CISOs

Despite continuous advances in security technologies, humans continue to be exploited by attackers. Credential abuse and social actions like phishing are major factors, accounting for around 60% of all breaches. These attacks rely less on technical vulnerabilities and more on exploiting human behavior and organizational processes. 

From my perspective as a former CISO, protecting humans concentrates three of today’s most pressing challenges: the sheer volume of email-based threats, their increasing sophistication, and the limitations of traditional employee awareness programs in moving the needle on risk. 

My personal experience of security awareness training as a CISO

With over 20 years’ experience as an ICT and Cybersecurity leader across various international organizations, I’ve seen security awareness training (SAT) in many guises. And while the cyber landscape is evolving in every direction, the effectiveness of SAT is reaching a plateau.  

Most programs I’ve seen follow a familiar pattern. Training is delivered through a combination of eLearning modules and internal sessions designed to reinforce IT policies. Employees are typically required to complete a slide deck or video, followed by a multiple-choice quiz. Occasional phishing simulations are distributed throughout the year.

The content is often static and unpersonalized, based on known threats that may already be outdated. Every employee regardless of role or risk exposure receives the same training and the same simulated phishing templates, from front-desk staff to the CEO.

The problem with traditional SAT programs

The issue with the approach to SAT outlined above is that the distribution of power is imbalanced. Humans will always be fallible, particularly when faced with increasingly sophisticated attacks. Providing generic, low-context training risks creating false confidence rather than genuine resilience. Let’s look at some of the problems in detail.

Timing and delivery

Employees today operate under constant cognitive load, making lots of rapid decisions every day to reduce their email volumes. Yet if employees are completing training annually, or on an ad hoc basis, it becomes a standalone occurrence rather than a continuous habit.  

As a result, retention is low. Employees often forget the lessons within weeks, a phenomenon known as the ‘Ebbinghaus Forgetting Curve.’

The graph illustrates that when you first learn something, the information disappears at an exponential rate without retention. In fact, according to the curve, you forget 50% of all new information within a day, and 90% of all new information within a week.  

Simultaneously, most training is conducted within a separate interface. Because it takes place away from the actual moment of decision-making, the "teachable moment" is lost. There is a cognitive disconnect between the action (clicking a link in Outlook) and the education (watching a video in a browser). 

People

In the context of professional risk management, the risks faced by different users are different. Static learning such as everyone receiving the same ‘Password Reset’ email doesn’t help users prepare for the specific threats they are likely to face. It also contributes to user fatigue, driven by repetitive training. And if users receive tests at the same time, news spreads among colleagues, hurting the efficacy of the test.  

Staff turnover introduces further risk. In many organizations, new employees gain access to systems before receiving meaningful training, reducing onboarding to little more than policy acknowledgment.

Measuring success

In my experience, solutions are standalone, without any correlation to other tools in the security stack. In some cases, the programs are delivered by HR rather than the security team, creating a complete silo.  

As a result, SAT is often perceived as a compliance exercise rather than a capability building function. The result is that poor-quality training does little to reduce the likelihood of compromise, regardless of completion rates or quiz performance.

What a modern SAT solution should look like

For today’s CISO, email represents the convergence point of high-volume, high-impact, and human-centric threats. Despite significant security investments, it remains one of the most difficult channels to secure effectively. Given these constraints, CISOs must evolve their approach to SAT.

Success lies in a balanced strategy one that combines advanced technology, attack surface reduction, and pragmatic user enablement, without over-relying on human vigilance as the final line of defense.

This means moving beyond traditional SAT toward continuous, contextual awareness, realistic simulations, and tight integration with security outcomes.

Three requirements for a modern SAT solution

  • Invisible protection: The optimum security solution is one that assists users without impeding their experience. The objective is to enhance human capabilities, rather than simply delivering a lecture. 
  • Real-time feedback: Rather than a monthly quiz, the ideal system would provide a prompt or warning when a user is about to engage with something suspicious. 
  • Positive culture: Shifting the focus away from a "gotcha" culture, which is a contributing factor to a resentment, and instead empowers employees to serve as "sensors" for the company. 

Discover how personalized security coaching can strengthen your human layer and make your email defenses more resilient. Explore Darktrace / Adaptive Human Defense.

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About the author
Karim Benslimane
VP, Field CISO
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