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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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June 2, 2026

Stopping Stealth Attacks with Precision: How Núclea Prevented a Breach Without Disruption

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Núclea is a Brazilian data and technology company that supports the country’s financial system by delivering digital services exclusively to banks and financial institutions. Operating in an environment where trust, availability, and data integrity are critical, the company faces a threat landscape that has evolved rapidly—particularly with the rise of AI-driven cyberattacks.

Brazil has experienced a wave of successful cyber incidents targeting financial institutions, many of them enabled by insiders or compromised credentials. The result was a noticeable shift in attacker strategy: instead of focusing on end customers, threat actors began targeting the institutions and platforms that underpin the financial ecosystem itself.

“Attacks became far more directed and contextual,” explains Guilherme, who leads incident response within Núclea’s security platform engineering team. “They weren’t noisy or obviously malicious—they were precise, patient, and designed to blend into normal operations.”

That precision was on full display in January 2026, when Núclea faced one of the most convincing phishing attacks the team had seen.

A real attack, built on trust and context

The attack began with a seemingly routine email.

It was sent from a real Brazilian government institution, using legitimate infrastructure and valid credentials that were later confirmed to have been compromised. Núclea had an established, ongoing relationship with this organization, and the email’s language, tone, and subject matter aligned perfectly with the type of communication the recipient team handled every day.

Attached to the email was a PDF document containing content that looked entirely legitimate.

The problem? A single URL embedded inside that PDF.

“The message itself was correct. The sender was real. The context was familiar. Even the document content made sense,” Guilherme explains. “There was just one small element that didn’t belong.”

That small detail was enough to initiate a full attack chain.

What the attackers were trying to do

If clicked, the URL would have downloaded a malicious payload designed to:

  • Collect information about the user and device
  • Identify where the system was located within the financial ecosystem
  • Install remote access tools to maintain control
  • Deploy an infostealer to extract sensitive data
  • Execute anti-forensic scripts to erase traces of the intrusion

In other words, it was a carefully engineered operation designed for persistence and stealth, not immediate disruption.

The attack also employed urgency—a classic social engineering technique. When the link didn’t open as expected, employees requested assistance from the security team, insisting the document was important and needed to be accessed quickly.

This is precisely the kind of scenario where traditional security tools struggle: almost everything about the interaction is legitimate.

Where Darktrace made the difference

Instead of blocking the entire message or relying on known indicators of compromise, Darktrace focused on behavioral context.

Darktrace recognized:

  • That the sending organization was normally trusted
  • That the communication pattern matched historical behavior
  • That the PDF content itself was not suspicious

But it also identified that the URL embedded within the document deviated from established behavioral patterns.

Rather than disrupting business operations, Darktrace took precise action: it rewrote the URL, preventing the malicious download while leaving the rest of the email untouched.

“When we analyzed it afterward, it became clear how dangerous the attack would have been,” says Guilherme. “But it never progressed—because Darktrace acted at exactly the right point.”

Subsequent forensic analysis confirmed the payload’s malicious intent. The attack never succeeded.

Precision over disruption

For Núclea, this incident reinforced a critical lesson: modern attacks don’t always look malicious—they hide within normal activity.

“What stands out to me is the precision,” Guilherme says. “Darktrace doesn’t rely on big, obvious signals. It’s effective in situations that fall outside the standard patterns we all know.”

Building resilience in a high trust ecosystem

For Núclea, cybersecurity is not just a defensive measure—it’s a business enabler.

Availability failures or successful breaches in the financial ecosystem can have immediate, large-scale consequences, from financial loss to reputational damage. Preventing those outcomes protects not just Núclea, but its partners and customers as well.

“Cyber resilience means keeping the business running—even under attack,” Guilherme explains. “And that requires people, processes, and technology working together.”

As AI continues to accelerate both attacks and defenses, the role of security is evolving. Precision, behavioral understanding, and intelligent automation are no longer optional—they’re essential.

“The easy days were yesterday,” Guilherme says. “The challenges ahead are bigger. We need to be prepared—internally and with partners that help us build resilience.”

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June 1, 2026

Defend What You Trust: Stories from the Front Lines of Modern Cyber Defense

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Modern attacks don’t always announce themselves, follow obvious patterns, or rely on known malware. Often, they move quietly inside trusted systems, authenticated sessions, and everyday behavior.

They don’t break in. They blend in.

That’s why an AI-powered defense is essential. It turns invisible signals into actionable insights at a scale neither analysts nor traditional tools can achieve alone.

Confidence is creating risk

One of the most dangerous assumptions in cybersecurity today is that strong controls equal strong protection.

Multi-factor authentication (MFA), for example, is widely viewed as a foundational safeguard. But as the CISO for a professional sports organization explains, that confidence can be misplaced. “A lot of organizations assume that once you have MFA, those accounts are safe. That’s not true.”

In one instance, his team identified a sophisticated attack where a threat actor bypassed MFA entirely, not by breaking it, but by going around it. A user’s authenticated session was hijacked and re-used, allowing the attacker to impersonate them without triggering traditional controls.

“Darktrace picked up that a session had been re-injected by the hacker, and we were able to block it right away,” he explains.

Attackers anticipate what we miss

Even well-trained users can become entry points.

“An email bypassed our existing security tools,” shares the VP of IT at a U.S.-based risk management services provider.  “The user missed one signal and entered their credentials into a malicious site. That’s what the bad guys count on.”

The organization responded quickly, but not before damage was done. Crucially, this occurred while Darktrace was in “watch mode,” before autonomous response was fully enabled. “Darktrace would have seen that and shut it down immediately,” he notes.

Mistakes and oversights like misconfigurations, forgotten machines, and missed patches can create serious vulnerabilities.

The CIO of a utility services organization shares an instance when Darktrace detected a breach to a client’s network via their ZTNA VPN due to misconfigured MFA. “Darktrace alerted us and autonomously blocked the scanning, preventing what could have been a ransomware-type incident.”  

The most dangerous threats are already inside

The Head of Security at a global business services provider knows firsthand how blind spots can persist inside environments. His team uncovered evidence of dormant ransomware artifacts sitting unnoticed within a company’s environment ¬¬– long before modern detection was in place.

“During a routine file transfer, Darktrace flagged the suspicious activity, identified the ransomware, and immediately quarantined the server,” he recalls.  While the attack was never executed, the implication was significant: the risk existed long before it was finally detected.

Cyber threats are also successful because they take advantage of normal human behavior, exploiting moments of cognitive overload, urgency, and trust.

The Executive Director of IT and Business Applications at a pharmaceutical lab describes the time Darktrace flagged an employee logging into Microsoft 365 from Singapore, despite him being physically located in the U.S. Darktrace immediately cut off his access and within minutes revealed that the employee’s son was using a VPN to play a video game.

While the threat was benign, it demonstrated the strength of AI to use contextual information to detect threats other tools miss. The information also saved security analysts hours of investigation and minimized downtime for the employee. “That level of precision and speed isn’t just convenient, it’s game changing.”

“Unusual” behavior is the new red flag

Detecting modern threats requires an understanding of what “normal” looks like and recognizing when something subtly deviates.

One security leader  at an AI technology enterprise described a scenario in which an employee connected to a proxy service in China. The service itself was legitimate, and although traditional tools didn’t flag it, the behavior was unusual for that user specifically.

“That’s what Darktrace picked up on. The activity turned out to be benign, but without visibility into behavioral deviations, it could just as easily have been something more serious.”

AI shifts defense from reaction to anticipation

These stories point to a fundamental shift by cyber attackers, both tactically and strategically. Because traditional security tools were built to detect what’s already known, modern attacks are often:

  • Credential-based, not malware-based
  • Behavioral, not signature-based
  • Subtle, not overt

They may operate within the boundaries of what appears normal, exploiting what organizations trust, not what they block:

  • Trusted sessions
  • Legitimate services
  • Human error

This is where AI is changing the equation. Rather than relying on predefined rules or known threat signatures, AI can:

  • Establish a baseline of normal behavior
  • Detect subtle anomalies in real time
  • Act autonomously to contain potential threats

Resilience, not perfection, is the new security standard

As these frontline experiences show, the organizations that lead are those that move beyond reactive defense and embrace AI as a core part of their strategy.

It eliminates the blind spots and uncertainty, says the CISO of a professional sports organization. “If you lack visibility, you’re not managing risk, you’re assuming it. AI gives you the actionable insights needed to turn uncertainty into control.”

And it provides the speed and agility that are vital when seconds matter, says the Executive Director of IT and Business Applications. “When Darktrace alerted us at 3:00 am to a ransomware attack, it had already quarantined the affected systems, blocked the attacker’s access, and provided us with the critical details and time needed to investigate. That action likely saved us hundreds of thousands, if not millions, of dollars.”

The modern SOC has become a cornerstone of enterprise resilience, responsible for protecting data and operational continuity while enabling digital growth and innovation. For today’s security professional, that means success is no longer measured by what they keep out, but by what they protect: revenue, reputation, and trust.

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