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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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May 19, 2026

State of AI Cybersecurity 2026: 77% of security stacks include AI, but trust is lagging

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

AI is a contributing member of nearly every modern cybersecurity team. As we discussed earlier in this blog series, rapid AI adoption is expanding the attack surface in ways that security professionals have never before experienced while also empowering attackers to operate at unprecedented speed and scale. It’s only logical that defenders are harnessing the power of AI to fight back.

After all, AI can help cybersecurity teams spot the subtle signs of novel threats before humans can, investigate events more quickly and thoroughly, and automate response. But although AI has been widely adopted, this technology is also frequently misunderstood, and occasionally viewed with suspicion.

For CISOs, the cybersecurity marketplace can be noisy. Making sense of competing vendors’ claims to distinguish the solutions that truly deliver on AI’s full potential from those that do not isn’t always easy. Without a nuanced understanding of the different types of AI used across the cybersecurity stack, it is difficult to make informed decisions about which vendors to work with or how to gain the most value from their solutions. Many security leaders are turning to Managed Security Service Providers (MSSPs) for guidance and support.

The right kinds of AI in the right places?

Back in 2024, when we first conducted this annual survey, more than a quarter of respondents were only vaguely familiar with generative AI or hadn’t heard of it at all. Today, GenAI plays a role in 77% of security stacks. This percentage marks a rapid increase in both awareness and adoption over a relatively short period of time.

According to security professionals, different types of AI are widely integrated into cybersecurity tooling:

  • 67% report that their organization’s security stack uses supervised machine learning
  • 67% report that theirs uses agentic AI
  • 58% report that theirs uses natural language processing (NLP)
  • 35% report that theirs uses unsupervised machine learning

But their responses suggest that organizations aren’t always using the most valuable types of AI for the most relevant use cases.

Despite all the recent attention AI has gotten, supervised machine learning isn’t new. Cybersecurity vendors have been experimenting with models trained on hand-labeled datasets for over a decade. These systems are fed large numbers of examples of malicious activity – for instance, strains of ransomware – and use these examples to generalize common indicators of maliciousness – such as the TTPs of multiple known ransomware strains – so that the models can identify similar attacks in the future. This approach is more effective than signature-based detection, since it isn’t tied to an individual byte sequence or file hash. However, supervised machine learning models can miss patterns or features outside the training data set. When adversarial behavior shifts, these systems can’t easily pivot.

Unsupervised machine learning, by contrast, can identify key patterns and trends in unlabeled data without human input. This enables it to classify information independently and detect anomalies without needing to be taught about past threats. Unsupervised learning can continuously learn about an environment and adapt in real time.

One key distinction between supervised and unsupervised machine learning is that supervised learning algorithms require periodic updating and re-training, whereas unsupervised machine learning trains itself while it works.

The question of trust

Even as AI moves into the mainstream, security professionals are eyeing it with a mix of enthusiasm and caution. Although 89% say they have good visibility into the reasoning behind AI-generated outputs, 74% are limiting AI’s ability to take autonomous action in their SOC until explainability improves. 86% do not allow AI to take even small remediation actions without human oversight.

This model, commonly known as “human in the loop,” is currently the norm across the industry. It seems like a best-of-both-worlds approach that allows teams to experience the benefits of AI-accelerated response without relinquishing control – or needing to trust an AI system.

Keeping humans somewhat in the loop is essential for getting the best out of AI. Analysts will always need to review alerts, make judgement calls, and set guardrails for AI's behavior. Their input helps AI models better understand what “normal” looks like, improving their accuracy over time.

However, relying on human confirmation has real costs – it delays response, increases the cognitive burden analysts must bear, and creates potential coverage gaps when security teams are overwhelmed or unavailable. The traditional model, in which humans monitor and act on every alert, is no longer workable at scale.

If organizations depend too heavily on in-the-loop humans, they risk recreating the very problem AI is meant to solve: backlogs of alerts waiting for analyst review. Removing the human from the loop can buy back valuable time, which analysts can then invest in building a proactive security posture. They can also focus more closely on the most critical incidents, where human attention is truly needed.

Allowing AI to operate autonomously requires trust in its decision-making. This trust can be built gradually over time, with autonomous operations expanding as trust grows. But it also requires knowledge and understanding of AI — what it is, how it works, and how best to deploy it at enterprise scale.

Looking for help in all the right places

To gain access to these capabilities in a way that’s efficient and scalable, growing numbers of security leaders are looking for outsourced support. In fact, 85% of security professionals prefer to obtain new SOC capabilities in the form of a managed service.

This makes sense: Managed Security Service Providers (MSSPs) can deliver deep, continuously available expertise without the cost and complexity of building an in-house team. Outsourcing also allows organizations to scale security coverage up or down as needs change, stay current with evolving threats and regulatory requirements, and leverage AI-native detection and response without needing to manage the AI tools themselves.

Preferences for MSSP-delivered security operations are particularly strong in the education, energy (87%), and healthcare sectors. This makes sense: all are high-value targets for threat actors, and all tend to have limited cybersecurity budgets, so the need for a partner who can deliver affordable access to expertise at scale is strong. Retailers also voiced a strong preference for MSSP-delivered services. These companies are tasked with managing large volumes of consumer personal and financial data, and with transforming an industry traditionally thought of as a late adopter to a vanguard of cyber defense. Technology companies, too, have a marked preference for SOC capabilities delivered by MSSPs. This may simply be because they understand the complexity of the threat landscape – and the advantages of specialized expertise — so well.

In order to help as many organizations as possible – from major enterprises to small and midmarket companies – benefit from enterprise-grade, AI-native security, Darktrace is making it easier for MSSPs to deliver its technology. The ActiveAI Security Portal introduces an alert dashboard designed to increase the speed and efficiency of alert triage, while a new AI-powered managed email security solution is giving MSSPs an edge in the never-ending fight against advanced phishing attacks – helping partners as well as organizations succeed on the frontlines of cyber defense.

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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May 18, 2026

AI Insider Threats: How Generative AI is Changing Insider Risk

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How generative AI changes insider behavior

AI systems, especially generative platforms such as chatbots, are designed for engagement with humans. They are equipped with extraordinary human-like responses that can both confirm, and inflate, human ideas and ideology; offering an appealing cognitive partnership between machine and human.  When considering this against the threat posed by insiders, the type of diverse engagement offered by AI can greatly increase the speed of an insider event, and can facilitate new attack platforms to carry out insider acts.  

This article offers analysis on how to consider this new paradigm of insider risk, and outlines key governance principles for CISOs, CSOs and SOC managers to manage the threats inherent with AI-powered insider risk.

What is an insider threat?

There are many industry or government definitions of what constitutes insider threat. At its heart, it relates to the harm created when trusted access to sensitive information, assets or personnel is abused bywith malicious intent, or through negligent activities.  

Traditional methodologies to manage insider threat have relied on two main concepts: assurance of individuals with access to sensitive assets, and a layered defense system to monitor for any breach of vulnerability. This is often done both before, and after access has been granted.  In the pre-access state, assurance is gained through security or recruitment checks. Once access is granted, controls such as privileged access, and zero-trust architecture offer defensive layers.

How does AI change the insider threat paradigm?

While these two concepts remain central to the management of insider threats, the introduction of AI offers three key new aspects that will re-shape the paradigm:.  

AI can act as a cognitive amplifier, influencing and affecting the motivations that can lead to insider-related activity. This is especially relevant for the deliberate insider - someone who is considering an act of insider harm. These individuals can now turn to AI systems to validate their thinking, provide unique insights, and, crucially, offer encouragement to act. With generative systems hard-wired to engage and agree with users, this can turn a helpful AI system into a dangerous AI hype machine for those with harmful insider intent.  

AI can act as an operational enabler. AI can now develop and increase the range of tools needed to carry out insider acts. New social engineering platforms such as vishing and deepfakes give adversaries a new edge to create insider harm. AI can generate solutions and operational platforms at increasing speeds; often without the need for human subject matter expertise to execute the activities. As one bar for advanced AI capabilities continues to be raised, the bar needed to make use of those platforms has become significantly lower.

AI can act as a semi-autonomous insider, particularly when agentic AI systems or non-human identities are provided broad levels of autonomy; creating a vector of insider acts with little-to-no human oversight or control. As AI agents assume many of the orchestration layers once reserved for humans, they do so without some of the restricted permissions that generally bind service accounts. With broad levels of accessibility and authority, these non-human identities (NHIs) can themselves become targets of insider intent.  Commonly, this refers to the increasing risks of prompt injection, poisoning, or other types of embedded bias. In many ways, this mirrors the risks of social engineering traditionally faced by humans. Even without deliberate or malicious efforts to corrupt them, AI systems and AI agents can carry out unintended actions; creating vulnerabilities and opportunities for insider harm.

How to defend against AI-powered insider threats

The increasing attack surfaces created or facilitated by AI is a growing concern.  In Darktrace’s own AI cybersecurity research, the risks introduced, and acknowledged, through the proliferation of AI tools and systems continues to outstrip traditional policies and governance guardrails. 22% of respondents in the survey cited ‘insider misuse aided by generative AI’ as a major threat concern.  And yet, in the same survey, only 37% of all respondents have formal policies in place to manage the safe and responsible use of AI.  This draws a significant and worrying delta between the known risks and threat concerns, and the ability (and resources) to mitigate them.

What can CISOs and SOC leaders do to protect their organization from AI insider threats?  

Given the rapid adaptation, adoption, and scale of AI systems, implementing the right levels of AI governance is non-negotiable. Getting the correct balance between AI-driven productivity gains and careful compliance will lead to long-term benefits. Adapting traditional insider threat structures to account for newer risks posed through the use of AI will be crucial. And understanding the value of AI systems that add to your cybersecurity resilience rather than imperil it will be essential.

For those responsible for the security and protection of their business assets and data holdings, the way AI has changed the paradigm of insider threats can seem daunting.  Adopting strong, and suitable AI governance can become difficult to introduce due to the volume and complexity of systems needed to be monitored. As well as traditional insider threat mitigations such as user monitoring, access controls and active management, the speed and autonomy of some AI systems need different, as well as additional layers of control.  

How Darktrace helps protect against AI-powered insider threats

Darktrace has demonstrated that, through platforms such as our proprietary Cyber AI Analyst, and our latest product Darktrace / SECURE AI, there are ways AI systems can be self-learning, self-critical and resilient to unpredictable AI behavior whilst still offering impressive returns; complementing traditional SOC and CISO strategies to combat insider threat.  

With / SECURE AI, some of the ephemeral risks drawn through AI use can be more easily governed.  Specifically, the ability to monitor conversational prompts (which can both affect AI outputs as well as highlight potential attempts at manipulation of AI; raising early flags of insider intent); the real-time observation of AI usage and development (highlighting potential blind-spots between AI development and deployment); shadow AI detection (surfacing unapproved tools and agents across your IT stack) and; the ability to know which identities (human or non-human) have permission access. All these features build on the existing foundations of strong insider threat management structures.  

How to take a defense-in-depth approach to AI-powered insider threats

Even without these tools, there are four key areas where robust, more effective controls can mitigate AI-powered insider threat.  Each of the below offers a defencce-in-depth approach: layering acknowledgement and understanding of an insider vector with controls that can bolster your defenses.  

Identity and access controls

Having a clear understanding of the entities that can access your sensitive information, assets and personnel is the first step in understanding the landscape in which insider harm can occur.  AI has shown that it is not just flesh and bone operators who can administer insider threats; Non-Human Identities (such as agentic AI systems) can operate with autonomy and freedom if they have the right credentials. By treating NHIs in the same way as human operators (rather than helpful machine-based tools), and adding similar mitigation and management controls, you can protect both your business, and your business-based identities from insider-related attention.

Visibility and shadow AI detection

Configuring AI systems carefully, as well as maintaining internal monitoring, can help identify ‘shadow AI’ usage; defined as the use of unsanctioned AI tools within the workplace1 (this topic was researched in Darktrace’s own paper on "How to secure AI in the enterprise". The adoption of shadow AI could be the result of deliberate preference, or ‘shortcutting’; where individuals use systems and models they are familiar with, even if unsanctioned. As well as some performance risks inherent with the use of shadow AI (such as data leakage and unwanted actions), it could also be a dangerous precursor for insider-related harm (either through deliberate attempts to subvert regular monitoring, or by opening vulnerabilities through unpatched or unaccredited tooling).

Prompt and Output Guardrails

The ability to introduce guardrails for AI systems offers something of a traditional “perimeter protection” layer in AI defense architecture; checking prompts and outputs against known threat vectors, or insider threat methodologies. Alone, such traditional guardrails offer limited assurance.  But, if tied with behavior-centric threat detection, and an enforcement system that deters both malicious and accidental insider activities, this would offer considerable defense- in- depth containment.  

Forensic logging and incident readiness response

The need for detection, data capture, forensics, and investigation are inherent elements of any good insider threat strategy. To fully understand the extent or scope of any suspected insider activity (such as understanding if it was deliberate, targeted, or likely to occur again), this rich vein of analysis could prove invaluable.  As the nature of business increasingly turns ephemeral; with assets secured in remote containers, information parsed through temporary or cloud-based architecture, and access nodes distributed beyond the immediate visibility of internal security teams, the development of AI governance through containment, detection, and enforcement will grow ever more important.

Enabling these controls can offer visibility and supervision over some of the often-expressed risks about AI management. With the right kind of data analytics, and with appropriate human oversight for high-risk actions, it can illuminate the core concerns expressed through a new paradigm of AI-powered insider threats by:

  • Ensuring deliberately mis-configured AI systems are exposed through regular monitoring.
  • Highlighting changes in systems-based activity that might indicate harmful insider actions; whether malicious or accidental.
  • Promoting a secure-by-design process that discourages and deters insider-related ambitions.
  • Ensuring the control plane for identity-based access spans humans, NHIs and AI models, and:
  • Offering positive containment strategies that will help curate the extent of AI control, and minimize unwanted activities.

Why insider threat remains a human challenge

At its root, and however it has been configured, AI is still an algorithmic tool; something designed to automate, process and manage computational functions at machine speed, and boost productivity.  Even with the best cybersecurity defenses in place, the success of an insider threat management program will still depend on the ability of human operators to identify, triage, and manage the insider threat attack surface.  

AI governance policies, human-in-the-loop break points, and automated monitoring functions will not guard against acts of insider harm unless there is intention to manage this proactively, and through a strong culture of how to guard against abuses of trust and responsibility.

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About the author
Jason Lusted
AI Governance Advisor
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