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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 7, 2026

Securing AI: Analysis of the Complete Security Stack with Governance and Controls

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Why traditional cybersecurity approaches are not enough for AI

AI adoption outpaces most security programs’ ability to adapt.  That gap is now one of the most consequential sources of cyber risk facing enterprises. As organizations embed generative and agentic AI into development workflows, business operations, and security tooling itself, the question is no longer whether AI will introduce risk. The question is whether organizations understand where that risk actually lives and how to manage it operationally.  

Two recent pieces of guidance underscore this shift:

  1. The upcoming Cybersecurity Framework Profile for AI from NIST
  1. The Five Eyes government guidance on the careful adoption of agentic AI services

Taken together, they point to a critical conclusion. AI security cannot be reduced to model hardening or prompt filtering. It requires a defense in depth strategy that treats AI as both a new attack surface and a force multiplier for defense, while accounting for how AI fundamentally changes scale, speed, and autonomy.  

Recent threat research suggests that today's cyber risk is driven less by initial compromise and more by an adversary's ability to blend into normal operations over time. AI systems create the same exposure in a new form: more autonomy, more scale, and more opportunities for risky behavior to blend into normal operations.

How NIST defines the three core pillars of AI security

The NIST profile organizes AI risk across three inseparable focus areas that span all cybersecurity functions, Secure, Defend and Thwart. These areas are not sequential. They exist simultaneously and must be addressed together.

Secure

This treats AI as an attack surface. It includes models, prompts, agents, pipelines, training and inference data, retrieval augmented generation corpora, and the AI supply chain itself. AI systems are opaque, probabilistic, and non-deterministic by design. Some vulnerabilities are inherent in how models are trained or how data is sourced. Traditional patching does not fully mitigate these risks. This is also where many enterprises are weakest today and, critically, where many security programs stop.  

Defend

This is AI as a defensive force multiplier. AI can improve detection speed, scale, correlation, and response, but only if the right models are used and operationalized correctly. Machine-speed behavior-based detection, response and containment becomes critical in defending non-deterministic systems. Accuracy, explainability, governance, testing, validation, and integration into SOC workflows matter as much as capability. Without those controls, hallucination risk, over automation, and misplaced trust become security risks themselves.  

Thwart

This treats AI as an adversarial accelerant. Threat actors are already using AI to generate targeted social engineering attacks, deepfakes, malware, and autonomous attack agents. Asymmetric warfare is highlighting faster vulnerability discovery and exploitation with a lag on patch development, testing and deployment.  

How this looks in practice

Darktrace researchers observed scaled, automated exploitation of the React2Shell vulnerability within days of disclosure. A vulnerable cloud asset was exploited in under 120 seconds of being deployed. Darktrace research team observed an AI/LLM-generated malware sample used in exploitation activity tied to React2Shell. The significance isn't novelty. It is that AI lowers the barrier to producing usable offensive tooling and compresses the time between experimentation and deployment.  

Tactics are getting more and more creative in order to string together steps of an attack kill chain. This creates a dependency on behavior-based detection, autonomous investigation, autonomous containment, training, resilience investment, and recovery planning across the entire enterprise.

Why agentic AI fundamentally changes enterprise cyber risk

The Five Eyes guidance on agentic AI highlights material changes to the cyber risk profile of an organization. Unlike generative AI systems that produce content for human consumption, agentic AI systems reason, plan, and act autonomously across tools, data, and environments. That autonomy, combined with access to real systems, amplifies the impact of traditional cyber failures and introduces new system level risks that are difficult to predict, observe, and contain.  

Risk in agentic systems does not live in the model alone. It emerges from interactions between models, prompts, memory, tools, APIs, identities, privileges, inter-agent trust relationships, and human assumptions baked into design. Vulnerabilities are often introduced through data, connectors, natural language interfaces, protocols, and drift by design.

In supply-chain incidents, attackers did not need sophisticated exploits to scale impact. They abused trusted systems built for automation and implicit access. Agentic AI inherits that model. Once a system can act across tools, data, and workflows, compromise propagates through trust relationships that were never designed for machine autonomy.

The major agentic AI risk classes include the following:  

  • The identity control for non-human identities or autonomous agents makes it difficult to mitigate over-permissioning, limiting access, scope, and duration, as well as access hygiene
  • Agents are frequently over permissioned
  • Compromised tools inherit agent authority
  • Static secrets enable impersonation
  • Implicit trust between agents enables lateral movement

Design and configuration risks compound this, including privileges evaluated once at startup, poor segmentation, unvetted third party tools, reused authorization decisions outside their original context, and guardrail limitations.  

Behavioral risk  

Agents can optimize for goals in unsafe ways, misinterpret ambiguous intent, chain actions into unintended sequences, change behavior during evaluation, and exhibit deceptive or sycophantic responses.  

Structural risk  

Structural risk follows from agentic systems that are tightly coupled, multicomponent ecosystems. Failures can propagate across agents. Hallucinations cascade downstream. Resource exhaustion becomes systemic. Tool misuse enables indirect prompt injection and command execution. Rogue agents can poison peer agents through trust relationships.  

Accountability

Accountability becomes unclear as autonomy increases. Autonomous agents assume human identity permissions, and humans should have clear ownership of these agents, but they don’t, and this model is flawed. Decision paths are opaque and non-deterministic. Logs are fragmented and difficult to interpret. Reproducing an incident will be impossible without explicit design for observability and forensics. An agent compromise is functionally an insider threat, often with better access and fewer behavioral constraints than a human.  

What does defense in depth look like for AI?

Agentic AI runs on software, networks, identities, and data. It must be governed using the same foundational principles that have proven resilient under uncertainty, including secure by design, defense in depth, zero trust, least privilege, continuous monitoring, behavior-based advanced threat detection and containment, and incident response and recovery.

Core components to a Defense in depth Strategy for Securing the use of AI:

  • Strong, precise identity control plane to include an identity per agent (cryptographic, non‑shared)
    • Privilege monitoring and just‑in‑time access
  • Data Governance
  • Secure‑by‑default configurations
    • Security Posture Management  
    • Zero Trust principles  
  • Strong guardrails, deny‑by‑default policies, and isolation
  • Explicit instruction hierarchies and controlled context
  • Behavioral-based detection across entire enterprise to include inputs, tools, and outputs as well as AI used on the endpoint, across the network, cloud, SaaS, email, and OT
    • Runtime anomaly detection and goal‑drift detection
    • Autonomous containment to mitigate risk and minimize damage
  • Hard boundaries on autonomy and delegation
  • Testing, Evaluation, Validation and Verification  
    • Determine when autonomous action and when human in the loop
    • Adversarial training and agent‑specific testing
    • Simulation, red teaming, and chaos testing
  • Kill‑switches, rollback, and containment mechanisms
    • Forensics data captures, interpretability, autonomous containment, and remediation/recovery plans  

Until standards, tooling, and assurance methods mature, organizations should assume agentic AI systems will behave unexpectedly and design deployments around resilience, behavior-based detection, reversibility, and containment, not efficiency.

How security leaders should prepare for enterprise AI adoption

AI security is not model security alone. Data, pipelines, identities, and agents are first class assets. Many AI attacks succeed through standard cyber failures amplified by AI. Identity, data, and supply chain risk dominate. Behavior-based detection and response are critical, not optional. Logging, provenance, versioning, and forensics data capture of detections are mandatory because you cannot investigate or recover from AI incidents without them.  

Risk will often be visible in behavior before it is clearly defined in policy or guidance. The same pattern has been seen in pre-CVE disclosure detection, where abnormal activity appears before the industry has named or described the vulnerability. AI systems introduce that uncertainty by design.

Security leaders should prioritize controls before AI is fully deployed, avoid generic AI security checklists, integrate AI risk into existing cyber programs, and mitigate the risk of non-deterministic technology with continuous oversight, monitoring, behavior analytics, anomaly detection, autonomous investigation, and autonomous containment.

Visibility has a different connotation with AI. Previously, audit logging worked for software/people, but with Generative AI-based systems, interpretability and explainability is difficult to understand, you cannot "undo" what has been done, or see the logic or control a chain of events. This is why behavioral-based detections and containment becomes critical.  

What capabilities should every AI security program include?

If an organization asked “what must be in place before scaling AI?”:

  1. AI Risk board and approval workflow
  1. IAM + PAM for all AI services and agents
  1. AI asset inventory
  1. Prompt/output DLP with sanctioned AI access – This is not just pre- and post- filters, but behavior-based detections of semantic interface as well as behavior-based analysis of output with associated risk context.  
  1. Shadow AI identification
  1. Secure MLOps – This is an entire paper itself
  1. Runtime guardrails and tool restrictions
    • Including AI Gateway/SASE/Zero trust/
  1. Runtime security with behavior-based detections
    • Complete visibility, monitoring, behavior analytics, anomaly detection, risk/intent/context evaluation of anomalies, autonomous investigation and autonomous containment of all AI assets across endpoint, network, SaaS, SASE, cloud, OT, email, and messaging platforms
  1. Secure data pipelines and data governance
  1. SOC workflow changes from malicious classification workflows to behavior-based detection workflows
  1. Remediation plans for AI-related incidents  

Layered Governance and Security Stack for Securing AI  

The following outline considers governance and security tools that should be considered, well-integrated, deployed, tested, operationalized and embedded within security workflows. These tools and controls map to NIST’s CMF for AI.  

These considerations do not need to be implemented in order. Runtime Detect and Respond will help mitigate risk while Governance, Visibility, and Identity mature.

Category Tooling Controls
Governance & Visibility
  • AI asset inventory / AI CMDB
  • Shadow AI discovery
  • SaaS discovery
  • AI usage on non-endpoint managed systems via network or cloud telemetry
  • MCP server/client usage via protocols
  • Browser telemetry
  • Gateway or SASE telemetry
  • Establish a risk board to set up controls
  • Mandatory registration of AI systems
  • Owner, data classification, intended use, and risk tier
  • Supplier disclosure requirements
  • Risk mitigation plan for AI adoption, innovation, or development
Identity, Access & Agent Control

Non-human autonomous agents should not have the full permissions associated with a human user.

  • IAM with workload identities
  • PAM for AI service accounts
  • Secrets management with short-lived tokens
  • Zero Trust principles
  • Identity, permission, and token hygiene
  • Unique identities per model, agent, and pipeline
  • Least privilege for tools, data, and APIs
  • Explicit approval for autonomous actions
Data Security & Privacy
  • Data classification and labeling
  • Enterprise DLP across endpoint, email, network, cloud, and SaaS
  • Forensics data capture after risky detections
  • Prompt-level DLP through behavior-based semantic analysis with risk and intent context
  • Input/interface analysis for risky data requests
  • Output analysis for sensitive data
  • Data integrity evaluation
  • Retention and redaction policies for prompts and responses
Secure MLOps / LLMOps
  • Secure CI/CD with AI-specific gates
  • Model registries with approval workflows
  • Dependency, container, and artifact scanning
  • SBOM/AIBOM generation
  • IaC security scanning
  • Security posture management
  • Misconfiguration identification
  • Hardening recommendations
  • Signed models and prompts
  • Versioned datasets, configurations, logging, and controls
  • Securing data pipelines
  • Controlled promotion
  • Quality assurance
  • Adversarial testing
Runtime Security

Securing runtime goes beyond guardrails and model firewalls to include behavior-based detections, response, and containment.

  • Detection, monitoring, and SOC integration
  • Centralized visibility into prompts, outputs, and tool calls
  • AI-specific detections
  • Behavior-based detection for AI usage patterns
  • Model drift and behavior monitoring
  • Autonomous containment
  • Behavior-based detection of model inputs and outputs
  • Prompt injection detection
  • Model manipulation, including jailbreaking, poisoning, and related attacks
  • Sensitive data access attempts
  • Behavior-based detection across low-code agents, high-code agents, MCP clients and servers, endpoint, network, cloud, email, SaaS, SASE, IoT, and OT
  • Policy enforcement between users, models, tools, agents, SaaS models/tools, and MCP servers/clients
  • Risk, intent, and context evaluation for detections and response actions
Response & Recovery
  • Autonomous containment
  • AI-assisted playbooks
  • Forensics data capture for AI-related events
  • Model rollback mechanisms
  • Backup and restore for models and datasets
  • Kill switch for agents
  • Autonomous response to agents performing risky behaviors
  • Model and dataset rollback
  • Remediation plans
  • Tabletop exercises
  • Supplier coordination plans
  • Post-incident AI performance validation

AI security requires continuous visibility and behavioral detection

AI changes how fast systems move, how decisions are made, and how risk propagates. It does not change the fundamentals of security. Organizations that succeed will be the ones that apply those fundamentals rigorously, assume failure, and build systems that can detect, contain, and recover when AI behaves in ways they did not anticipate. Security is not what AI is allowed to do. It is whether the organization can understand, trust, and control what AI actually does in practice.  

Take this guidance to understand different initiatives that organizations should be considering. Securing AI is the most critical component to AI safety. As organizations invest more in AI adoption, they should be investing in security in order to mitigate the risk of AI adoption. Organizations should be evaluating their governance and security stack to include well-integrated tools that are deployed, tested, operationalized and embedded within security workflows. While organizations mature in governance, visibility and identity access management, they should be investing in behavior-based detection and autonomous containment to mitigate AI risk.  

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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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Andrew Hollister
Principal Solutions Engineer, Cyber Technician
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