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February 22, 2024

Attack Trends: VIP Impersonation in the Business Hierarchy

VIP Impersonation occurs when a cyber-threat actor impersonates a prominent employee to obtain sensitive data. Learn all about VIP impersonation 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
Kendra Gonzalez Duran
Principal Analyst
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22
Feb 2024

What is VIP impersonation?

VIP impersonation involves a threat actor impersonating a trusted, prominent figure at an organization in an attempt to solicit sensitive information from an employee.

VIP impersonation is a high-priority issue for security teams, but it can be difficult to assess the exact risks, and whether those are more critical than other types of compromise. Looking across a range of Darktrace/Email™ customer deployments, this blog explores the patterns of individuals targeted for impersonation and evaluates if these target priorities correspond with security teams' focus on protecting attack pathways to critical assets.

How do security teams stop VIP Impersonation?

Protecting VIP entities within an organization has long been a traditional focus for security teams. The assumption is that VIPs, due to their prominence, possess the greatest access to critical assets, making them prime targets for cyber threats.  

Email remains the predominant vector for attacks, with over 90% of breaches originating from malicious emails. However, the dynamics of email-based attacks are shifting, as the widespread use of generative AI is lowering the barrier to entry by allowing adversaries to create hyper-realistic emails with minimal errors.

Given these developments, it's worth asking the question – which entities (VIP/non-VIP) are most targeted by threat actors via email? And, more importantly – which entities (VIP/non-VIP) are more valuable if they are successfully compromised?

There are two types of VIPs:  

1. When referring to emails and phishing, VIPs are the users in an organization who are well known publicly.  

2. When referring to attack paths, VIPs are users in an organization that are known publicly and have access to highly privileged assets.  

Not every prominent user has access to critical assets, and not every user that has access to critical assets is prominent.  

Darktrace analysis of VIP impersonation

We analyzed patterns of attack pathways and phishing attempts across 20 customer deployments from a large, randomized pool encompassing a diverse range of organizations.  

Understanding Attack Pathways

Our observations revealed that 57% of low-difficulty attack paths originated from VIP entities, while 43% of observed low-difficulty attack paths towards critical assets or entities began through non-VIP users. This means that targeting VIPs is not the only way attackers can reach critical assets, and that non-VIP users must be considered as well.  

While the sample size prevents us from establishing statistical significance across all customers, the randomized selection lends credence to the generalizability of these findings to other environments.

Phishing Attempts  

On average, 1.35% of total emails sent to these customers exhibited significantly malicious properties associated with phishing or some form of impersonation. Strikingly, nearly half of these malicious emails (49.6%) were directed towards VIPs, while the rest were sent to non-VIPs. This near-equal split is worth noting, as attack paths show that non-VIPs also serve as potential entry points for targeting critical assets.  

Darktrace/Email UI
Figure 1: A phishing email actioned by Darktrace, sent to multiple VIP and non-VIP entities

For example, a recent phishing campaign targeted multiple customers across deployments, with five out of 13 emails specifically aimed at VIP users. Darktrace/Email actioned the malicious emails by double locking the links, holding the messages, and stripping the attachments.

Given that non-VIP users receive nearly half of the phishing or impersonation emails, it underscores the critical importance for security teams to recognize their blind spots in protecting critical assets. Overlooking the potential threat originating from non-VIP entities could lead to severe consequences. For instance, if a non-VIP user falls victim to a phishing attack or gets compromised, their credentials could be exploited to move laterally within the organization, potentially reaching critical assets.

This highlights the necessity for a sophisticated security tool that can identify targeted users, without the need for extensive customization and regardless of VIP status. By deploying a solution capable of promptly responding to email threats – including solicitation, phishing attempts, and impersonation – regardless of the status of the targeted user, security teams can significantly enhance their defense postures.

Darktrace vs Traditional Email Detection Methods

Traditional rules and signatures-based detection mechanisms fall short in identifying the evolving threats we’ve observed, due to their reliance on knowledge of past attacks to categorize emails.

Secure Email Gateway (SEG) or Integrated Cloud Email Security (ICES) tools categorize emails based on previous or known attacks, operating on a known-good or known-bad model. Even if tools use AI to automate this process, the approach is still fundamentally looking to the past and therefore vulnerable to unknown and zero-day threats.  

Darktrace uses AI to understand each unique organization and how its email environment interoperates with each user and device on the network. Consequently, it is able to identify the subtle deviations from normal behavior that qualify as suspicious. This approach goes beyond simplistic categorizations, considering factors such as the sender’s history and recipient’s exposure score.  

This nuanced analysis enables Darktrace to differentiate between genuine communications and malicious impersonation attempts. It automatically understands who is a VIP, without the need for manual input, and will action more strongly on incoming malicious emails  based on a user’s status.

Email does determine who is a VIP, without a need of manual input, and will action more strongly on incoming malicious emails.

Darktrace/Email also feeds into Darktrace’s preventative security tools, giving the interconnected AI engines further context for assessing the high-value targets and pathways to vital internal systems and assets that start via the inbox.

Leveraging AI for Enhanced Protection Across the Enterprise  

The efficacy of AI-driven security solutions lies in their ability to make informed decisions and recommendations based on real-time business data. By leveraging this data, AI driven solutions can identify exploitable attack pathways and an organizations most critical assets. Darktrace uniquely uses several forms of AI to equip security teams with the insights needed to make informed decisions about which pathways to secure, reducing human bias around the importance of protecting VIPs.

With the emergence of tools like AutoGPT, identifying potential targets for phishing attacks has become increasingly simplified. However, the real challenge lies in gaining a comprehensive understanding of all possible and low-difficulty attack paths leading to critical assets and identities within the organization.

At the same time, organizations need email tools that can leverage the understanding of users to prevent email threats from succeeding in the first instance. For every email and user, Darktrace/Email takes into consideration changes in behavior from the sender, recipient, content, and language, and many other factors.

Integrating Darktrace/Email with Darktrace’s attack path modeling capabilities enables comprehensive threat contextualization and facilitates a deeper understanding of attack pathways. This holistic approach ensures that all potential vulnerabilities, irrespective of the user's status, are addressed, strengthening the overall security posture.  

Conclusion

Contrary to conventional wisdom, our analysis suggests that the distinction between VIPs and non-VIPs in terms of susceptibility to impersonation and low-difficulty attack paths is not as pronounced as presumed. Therefore, security teams must adopt a proactive stance in safeguarding all pathways, rather than solely focusing on VIPs.  

Attack path modeling enhances Darktrace/Email's capabilities by providing crucial metrics on potential impact, damage, exposure, and weakness, enabling more targeted and effective threat mitigation strategies. For example, stronger email actions can be enforced for users who are known to have a high potential impact in case of compromise. 

In an era where cyber threats continue to evolve in complexity, an adaptive and non-siloed approach to securing inboxes, high-priority individuals, and critical assets is indispensable.  

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
Kendra Gonzalez Duran
Principal Analyst

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July 6, 2026

NIST Just Proved It: AI Security Can’t Be Solved With Rules

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Static AI guardrails are inherently limited

As organizations adopt generative AI, many still assume that the right set of guardrails will be enough. The problem is you can’t anticipate every way these systems might be misused, abused or attacked. What NIST has done is put a mathematical foundation under that intuition.

In recent research building on Gödel’s incompleteness theorems, which showed that any system built on a fixed set of rules will always have gaps, NIST demonstrates that there is no finite set of guardrails that can be universally robust against adversarial prompts. In plain terms, if your defense is based on a fixed set of rules, there will always be inputs that bypass them. Not because the rules are badly written, but because the problem space is bigger than static rules can ever cover.

This is not new in cybersecurity - detection rules have always had to live with this trade-off. What is different with GenAI is the scale and shape of that problem. These systems are built on human language, and human language is not bounded. It is fluid, contextual and deliberately ambiguous. The number of ways intent can be hidden is effectively limitless. You are not defending against a defined protocol or a fixed exploit chain. You are defending against the entire expressive capacity of people.

So attempting to create a complete set of rules is the wrong starting point. It assumes the problem can be deterministically described. NIST’s work shows that it cannot. Organizations still need a way to manage AI risk, but the traditional approach of defining allowed and disallowed patterns is always going to lag behind what is actually happening. The same input can be benign in one context and risky in another, and static rules struggle to capture that distinction.

The question then is what fills that gap?

AI security must shift from rules to behavior

What's required is a shift in what you are trying to understand. Rules try to describe what should and shouldn't happen. Behavior shows you what is happening. Or to put it another way, if inputs are unbounded and adversaries adapt, the only stable signal is behavior.

In a GenAI context, that means analyzing how an AI model is being used, how prompts evolve over time, how outputs are shaped, and where AI agent interactions start to drift from what is expected. It means moving from static definitions of bad to a more dynamic understanding of intent.

Instead of trying to predict every bad prompt, you focus on identifying when behavior starts to move outside expected norms. Instead of asking whether a single input matches a rule, you ask whether the overall pattern of activity makes sense for the system and how it’s being used.

Guardrails remain important but they are only one layer

This does not eliminate the need for guardrails. They still play a role. But they will never address the entire problem space and are simply one part of your defense in depth approach.

NIST’s proof is useful because it makes this explicit. It removes the assumption that with enough effort, a complete rule set is achievable. It isn’t.

Once you accept that, the shift becomes unavoidable. This is no longer a problem of writing better rules, but of understanding behavior in a space where the possible inputs are effectively unbounded.

For security leaders, that changes the nature of the problem. It is less about defining what should be allowed, and more about recognizing when something is no longer consistent with expected behavior.

That does not remove the need for guardrails, but it does change their role. They set boundaries, but they do not define understanding. The gap between the two is where risk now sits.

In the end, this is what “can’t be solved with rules” really means. Rules will always leave gaps, and those gaps are not theoretical. They show up in how systems actually behave Not what we expect them to do, or what we intended them to do, but what they are doing in practice. That is where the signal is, and increasingly, that is where the security problem sits.

References:

https://www.nist.gov/news-events/news/2026/06/nist-mathematical-proof-supports-transition-continuous-monitor-and-update

https://ieeexplore.ieee.org/document/11475847

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About the author
Andrew Hollister
Principal Solutions Engineer, Cyber Technician

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July 1, 2026

5 Ways AI is changing traditional security models according to modern CISOs

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The Reality of Securing AI in Motion

Traditional security tools were built for environments defined by fixed rules and predictable workflows. But AI behavior is non-deterministic. The same prompt can produce different outcomes, and risk often emerges gradually as AI behavior adapts, and permissions drift over time. This creates a constantly shifting environment where security teams are working to define control in a system that resists stability. “In AI security, yesterday's priorities can become tomorrow's blind spots. The landscape shifts that fast,” warned the SVP and Head of Technology and Cybersecurity of a real estate investment trust. Conventional approaches, which rely on establishing and maintaining a steady baseline, struggle to keep up with that level of change.

At the same time, AI adoption is accelerating across organizations, often faster than security teams can implement the controls needed to manage it. “The car is being built while it’s already on the road,” explained the CISO of a global private fund administrator. “The threats we're securing against today won't be the threats we're facing tomorrow. What kept us up three months ago looks nothing like what we're dealing with today.”

As businesses move quickly to unlock value from AI, security teams are left closing gaps in real time, while also facing adversaries who are using AI to make their attacks more scalable, adaptive, and difficult to detect. In this recent roundtable discussion of CISOs and security leaders, five themes emerged around AI cyber risk.  

1. AI agents with human access but no human judgment

In Darktrace’s 2026 State of AI Cybersecurity report, 96% of the surveyed security professionals agree that AI significantly improves the speed and efficiency with which they work. Yet, 92% admitted that they’re concerned with the security implications of the use of AI agents across their workforce.

AI agents now operate with human-level permissions across systems, acting at machine speed, orchestrating actions across platforms, and making decisions without the judgment or caution a person would apply. Unlike human users, they cannot be expected to pause and question whether a given action is appropriate.

Their identities are also difficult to inventory, govern, and audit. As agents become easier to deploy than legacy IT systems ever were, organizations are quickly losing track of what is running, what it has access to, and what it is doing. This creates a growing class of highly privileged, autonomous actors operating without the visibility or oversight that traditional identity and access controls were designed to provide.“While AI adoption is critical to running a modern business, AI alone can’t solve all our cybersecurity challenges,” said a global financial sector CISO. “We still need think critically and use human judgement. Those are two things AI can’t do.”

This lack of human judgment becomes especially risky as new architectures, such as Model Context Protocol (MCP), can expand how agents connect to data, tools, and external systems. By design, MCP enables agents to dynamically discover and interact with new resources, increasing flexibility but also introducing new pathways for unintended access, data exposure, or abuse if not properly governed.

The CISO of a fund administrator highlighted one emerging vector as an example: rogue MCP servers. “Our developers want to move quickly and bring value to the business, but technologies like these can unintentionally expose sensitive data in ways that would never have happened before.”

2. Increased digital complexity and expanded attack surface

AI activity rarely stays contained. A single prompt can trigger a chain of actions across networks, email, cloud infrastructure, SaaS platforms, endpoints, identity systems, and development environments, spanning systems that were never designed to be secured as a single, connected flow. This expands both the scale and complexity of what security teams need to monitor and defend.

Yet no single control has visibility across that entire chain. “You can’t defend effectively what you can’t see,” cautioned the private fund administrator CISO. As AI-driven activity moves fluidly across environments, gaps in coverage become inevitable, creating blind spots that attackers can exploit.

Threat actors are already capitalizing on this lack of visibility. “Threat actors have advanced their use of generative AI to launch more convincing phishing campaigns, automate social engineering, and scale attacks with greater precision down to the individual level,” said the SVP of Technology and Cybersecurity for the real estate investment trust. What was once manual and targeted can now be automated and personalized at scale, making attacks harder to detect and easier to execute.

At the same time, the pace of exploitation is accelerating. As a global CISO operating across 40+ countries described it: “Zero-day vulnerabilities are no longer zero day; it’s minus one day. By the time you get to it and address it, it’s already a problem.” By the time risk is identified, it has often already been realized.

The result is a rapidly expanding and increasingly interconnected attack surface that challenges security teams to maintain visibility, context, and control across AI-driven activity.

3. Shadow AI is already everywhere

76% of organizations now cite shadow AI as a problem, one that is spreading through organizations in ways that are hard to track and even harder to control.

Employees are experimenting with publicly available Gen AI tools. Teams are spinning up low-code automations on their own. SaaS providers are quietly embedding AI into existing products. Developers are plugging AI services directly into workflows, often without pausing to consider what that exposure means.

The result is a lack of visibility into:

  • What AI tools are being used
  • What data those tools can access
  • Where prompts and outputs are going
  • Which AI agents are interacting with enterprise systems

The SVP of Cybersecurity at a real estate investment trust described the shift: “Before, I was worried about someone sending data erroneously to their personal email. Now we have all these agents online that people are utilizing, and we’re looking at those vectors as well.” For security teams, this means operating without a complete view of how AI is being used, what it can access, and where risk may already be emerging.

4. Built-in guardrails are not enough

Organizations often assume that native AI guardrails or provider-level controls are sufficient to manage AI risk. But securing AI requires ongoing visibility, oversight, and governance, not just controls configured at deployment. "It’s a misconception that adopting AI is going to solve all your problems,” warns a global financial services CISO.

Security leaders are increasingly recognizing the limitations of these controls as:

  • Fragmented and difficult to enforce consistently across multiple AI systems, workflows, and environments
  • Ambiguous in terms of accountability due to shared responsibility for AI governance between IT, security, developers, business teams, and third-party providers
  • Limited in end-to-end oversight, leaving gaps that stretch from the initial prompt all the way through to the downstream impact of an agent's actions

Securing AI demands more than simple prompt filtering or static policy enforcement. It requires understanding intent, behavior, and context across both human and AI activity.

The next phase of cybersecurity: securing AI

To safely and responsibly adopt AI at scale, organizations need a new operational model for cybersecurity that’s capable of:

• Understanding AI behavior

• Identifying risk in real time

• Maintaining governance without slowing innovation

The CSO of a $10 billion municipal utility organization described the challenge with precision: “We have to move at the speed of innovation and risk, because both are accelerating faster than ever.”

Embrace AI with confidence with Darktrace / SECURE AI

Darktrace has introduced Darktrace / SECURE AI™, a new product within the Darktrace ActiveAI Security Platform™  ,designed to provide enterprise-wide security for AI by applying industry leading behavioral analysis to how prompts, agents, and AI systems are used.

Darktrace / SECURE AITM delivers real-time visibility and control across Enterprise and SaaS GenAI prompts, AI agent identities, development and production environments, and Shadow AI - detecting even subtle misuse, misconfiguration, and drift that traditional, rule-based controls simply do not understand. By interpreting context and intent across humans and machines, Darktrace enables organizations to adopt AI at scale without introducing unmanaged risk

What makes this possible is Darktrace’s decade-long maturity and expertise in behavioral understanding and AI-native cybersecurity. Achieved with Self-Learning AI that has been proven across more than 10,000 organizations, Darktrace understands what “normal” looks like for a business, across its users, systems, and now AI, so that meaningful deviations can be detected and acted on before they become incidents.

With one CISO describing Darktrace’s Self-Learning AI as “a leap forward compared to other tools” and another as a “force multiplier,” the technology can interpret ambiguous interactions, understand how access accumulates over time, and recognize when behavior, human or machine, begins to drift.

“Strategically, we’re looking to gain more visibility into how AI is operating across the environment and achieve greater control over what AI should be allowed to access and do,” shared the CISO at a private fund administrator.  

“What I’ve seen from Darktrace / SECURE AI is extremely promising. I have tremendous confidence in Darktrace’s vision for where this is headed and its ability to execute on this new solution.”

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