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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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September 17, 2026

The Problem of Re-defining Human Value in the Agentic Age

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Newsfeeds are constantly informing us about the rapid escalation of agentic AI systems. These systems move far beyond simple machine-based computations, and  the focused, defined and bounded assistance that most AI systems started out as.

The next evolution of AI will harness the agentic properties of orchestration, automation, and heightened value-chains in IT, taking on the burden of workflow management, not just workflow delivery.

In nearly all of these instances, promises are made such as ‘this will free up human time’ or ‘this will allow people to focus on higher-order strategy’. However that message is delivered, one thing is clear: in ceding the orchestration and management of work to increasingly sophisticated AI agents and agentic systems, human value will be elevated to a particular and specific layer: the ability to judge its outputs.  As AI takes on more tasks, humans should be able to focus on a higher level of governance; making sure the decisions that AI offers us are ethical, responsible and worthwhile.  

But there are two major problems with that approach.

This blog discusses the problem of how Agentic systems are re-shaping how we review information, where we fit in, and when we make decisions.  It also discusses the problem of how the increased flow of confident, generated information affects the way we make judgement.  This blog considers how human judgement needs to adapt, and how a behavioral defense approach – using techniques pioneered by Darktrace – can help us do that.

The challenge of knowing where human judgement belongs

As we confer more automated decision-making to agentic systems, it might look increasingly less like ‘granting permissions’, and more like ‘surrendering authority’.  

The judgement layer for AI-generated work is not a fixed boundary. We have become used to the idea of a ‘human in the loop’ (HITL) and, historically, relationships between humans and IT systems were reasonably clear and bounded.  Computer and software systems were programmed to carry out certain tasks or automated functions, and humans could control the gates and decision points where actions were undertaken. Even across highly complex computational workflows, human interaction was a controllable node within the process; we were able to configure and regulate. But in the agentic age, where that human interaction sits, and what it can influence shifts every time AI systems are granted autonomy.  

This leads us to the first problem: if humans are moving themselves (or are being moved) into the ‘judgement’ part of the value chain, exactly where and when do we exercise that judgement?  

Humans are no longer the sole shepherds of computer-based or software-controlled outputs.  We are at times at least one step further (and slower) behind the new agentic shepherds.  We might also be blind to what they are doing.  Not only might we be removed and blind to the actions of our AI shepherds, but with the challenge of unknown, unapproved AI systems operating beyond our control, humans might not even know that our work is being shepherded by an AI at all.  Simply put, with the advent of greater levels of autonomy and orchestration, humans are at risk of not even knowing where to apply our newly-extended powers of strategic judgement.

Shadow AI – the use of unapproved AI systems or processes – is a growing threat to the role of effective governance and oversight. Shadow AI isn't just the AI you can't see. Its the AI you already know about being used in an unapproved way. The ability to generate effective oversight of the AI systems you use (or that are used on your behalf) will be increasingly important to ensure that human judgement in the AI value chain is effective, and deliberately placed.

The problem of what makes good judgement

The second problem lies in how flawed human judgement can be.  Humans are historically, notoriously, and, sometimes dangerously, unreliable when it comes to exercising judgement.  Humans are prone to the worst kinds of bias, the seduction of malign influence, and the sometimes-overwhelming urge to succeed. AI has long had a known flaw of operating with sycophancy, providing outputs that tend to agree with or flatter the human user.  But as AI grows ever more effective, there is a risk of both hyper-enablement (where humans increasingly and knowingly enable AI despite potential harm), as well as the greater risk of suggestion. Both of these aspects could skew the newly-elevated input of human judgement.

Imagine a highly competent AI system that has just orchestrated and managed a dizzying array of processes and workflows.  The AI is designed to present the human decision-maker with recommendations; based on analysis, comparison and other programmed factors.  This is where the human judgement layer is enabled.  But what if that judgement is summarily diffused by an AI-based recommendation that emulates the decision, provides plausible but unattractive alternatives, then suggests (or, worse, directs) the human end-user to take a particular course of action.

The risk here is that you are given a recommendation, tailored to your preferences (which the AI has learned, or which you have divulged), and which appears to make perfect sense.  It appears to be a well-weighted recommendation, with sound arguments that tap into our inherent biases or inclinations so that a specific decision-path is followed. With the growth of agentic systems specifically designed to match user profiles (from Cowork agents to ‘digital twin’ models), the likelihood of agentic influence could badly skew human judgement or, at the least, devalue the proposition that humans are taking a higher-layer of strategic control over AI-based decisions.

If AI convincingly recommends something that may be problematic, it can be difficult to discern both accurate data, and the context required to make the right judgement.

Given the two problems described above, the job of exercising valuable human judgement in the agentic age can draw down to these two questions:

  • When should humans intervene in the agentic process?  
  • How can we make the best possible judgement calls?

What humans contribute that AI cannot

For all the flaws that make human judgement unreliable, people have the edge over even the most sophisticated and powerful AI systems when it comes to issues such as ethics and social context.  An AI system can, with startling granularity, rank the value of adopting a new business proposal: offering predictive metrics on costs, returns, market value, time-to-deliver operations, conformance with legal registers, etc.  But it can’t tell if the business proposal is ethically sound, or if the business venture will potentially affect groups outside of the analyzed proposal. It can’t tell you if the CEO has a ‘bad feeling’ about this effort.  It can’t tell you if this is the right thing to do.  

The ability to add social context, balance complex interpersonal dynamics, understand nuance, and to go beyond what seems economically reasonable is where human judgement can add value.  

Human judgement is difficult to encapsulate in metrics. And the way we train our development may need to adapt too. Rather than building up a gradual, experiential knowledge base, we should think about training the skill of judgement itself; especially for an agentic age.

How behavioral security strengthens AI governance

If this all feels like a vicious circle (‘I need AI help to make good judgements’ / ‘AI can twist what I need to judge’) it needn’t be. The key to this is having a defense-in-depth approach, with tools that can actually help.

This is precisely where behavioral security becomes important. The complex and nuanced way that humans exercise judgement is often rooted in our ability to recognize behavior that doesn't look right. We may not always be able to articulate it immediately, but we can often identify when an action, recommendation, or outcome feels inconsistent with the context around it. As AI systems take on more responsibility across the decision chain, preserving that ability to recognize meaningful deviations becomes increasingly important.

Darktrace’s / SECURE AI is designed to do exactly that. It applies behavioral security to AI ecosystems, helping organizations understand how people, AI tools, identities, and agents interact across the business. By learning the patterns of normal AI usage and surfacing activity that deviates from those patterns, it provides security teams with the context needed to investigate risk, understand unusual behavior, and make informed governance decisions. Rather than relying solely on predefined rules or assumptions, this behavioral understanding helps organizations distinguish between expected AI activity and behavior that warrants closer scrutiny.

This matters because we are already in an era of information overload. If humans are expected to elevate their value through strategic judgement, the ability to do this without being overwhelmed by data (good or bad) will be critical.  

We need the ability to discern when we're being misled by AI, and whether our judgement calls are being made on the basis of accurate, contextual information. Darktrace / SECURE AI provides that additional layer of defensive security for activity we cannot easily see. Whether it is suspected Shadow AI or skewed recommendations, the net result is a protected organization, where users can more effectively use AI to make positive judgements.

For those where that judgement is a critical skill (both individuals, as well as those working in security teams), improving our metacognition - the ability to understand information in a broader context - will supercharge the value of human judgement. When those judgements are grounded in context rather than assumptions we have better information to make sound decisions.

Conclusion

Human judgement is a skill that is honed over time and experience.  Darktrace’s / SECURE AI employs the same principles, but at machine-speed. Rather than influencing or directing, Darktrace / SECURE AI offers AI-enabled assurance; providing human-based judgement with the right context to make a balanced decision.  

What we judge can be valued by the legitimacy of its outputs. For AI, those outputs are valued on the speed and accuracy of the information provided.  Increasingly for humans, the value of our outputs will be based on the validity of our judgement, and how we justify our decisions in ways that engineer confidence.  

Humans often know more than we can express, while AI is prone to expressing more than it truly understands. Humans can bridge the context AI often fails to appreciate. When that judgement is supported by relevant, impartial AI systems, this is the future space where good AI governance will be exercised.

Discover Darktrace / SECURE AI.

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About the author
Jason Lusted
AI Governance Advisor

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September 4, 2026

Darktrace Advances Incident Investigation and AI-Agent Security with OpenAI Daybreak Models

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Earlier this year, Darktrace joined OpenAI’s Daybreak Defense Network to explore how their cyber capabilities can be integrated within Darktrace products and services to transform how security teams move from signal to action.

At the heart of this work is Darktrace's behavioral understanding of customer environments and identification of complex security incidents, combined with OpenAI models that can add context to help explain why an incident matters and its potential impact on the business. By bringing these capabilities into defensive workflows security teams already use, the goal is to give defenders not just greater visibility, but the context and guidance they need to act with confidence.

Since joining the program, we've been working with OpenAI to explore how these capabilities can address specific security challenges for defenders.

The problem we're solving

Attackers continue to change how they operate, including by using AI to increase the speed and scale of some techniques. Security teams are already managing a large volume of alerts, and the question isn't just what's happening, but how it could affect the organization. Even when an incident is fully investigated and correlated, technical severity alone doesn't tell a security team how much it actually matters to the business. That same challenge extends to internal AI adoption. As organizations adopt more AI systems and agents, security teams need visibility into their behavior, access and activity, along with the broader business context needed to identify and investigate potential risk.

Darktrace's Adaptive AI™ builds a detailed, organization-specific picture of what's normal for each environment, and uses that picture to investigate threats and identify complex security activity across domains. OpenAI's models can build on Darktrace's correlated, technically prioritized incidents by adding context that can help defenders understand what may be at stake.

What we're building

Our work is focused on two areas: supporting security investigation and response, and helping defenders identify risky behavior across enterprise AI systems and agents.

The first aligns Darktrace's behavioral understanding with OpenAI models to support  security investigation and prioritization. Darktrace's Adaptive AI continuously learns the unique patterns of normal behavior within each customer it protects, creating a deep, organization-specific understanding of its digital estate. When unusual activity emerges, OpenAI's models can draw on that context to help analysts investigate the incident, understand its significance and assess potential business consequences — reducing the need to manually assemble context from fragmented signals.

Second, we are exploring how these capabilities can support AI-agent and runtime security through Darktrace / SECURE AI™. OpenAI’s Daybreak models can build on the detections and visibility Darktrace / SECURE AI provides, connecting signals across a customer's environment and help defenders identify potentially risky behavior involving AI systems and agents. Activity that might appear isolated can instead be connected with related signals, helping defenders investigate the broader context and determine appropriate remediation.

Darktrace brings deep cybersecurity expertise, an evolving understanding of each customer's environment, and AI-driven identification of threats across the digital estate. Through the Daybreak Defense Network, Darktrace is exploring how OpenAI models can augment those capabilities in defensive security workflows — supporting incident investigation and response and improving visibility into AI-agent and runtime risk.

These capabilities are still in development, and we're excited to continue building on this work.

To learn more about how Darktrace continues to innovate to meet today's most pressing security challenges, register for our upcoming launch broadcast here.

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About the author
Dr. Tim Bazalgette
Chief AI Officer, Darktrace
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