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March 11, 2020

How Darktrace Antigena Email Caught A Fearware Email Attack

Darktrace effectively detects and neutralizes fearware attacks evading gateway security tools. Learn more about how Antigena Email outsmarts cyber-criminals.
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
Dan Fein
VP, Product
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11
Mar 2020

The cyber-criminals behind email attacks are well-researched and highly responsive to human behaviors and emotions, often seeking to evoke a specific reaction by leveraging topical information and current news. It’s therefore no surprise that attackers have attempted to latch onto COVID-19 in their latest effort to convince users to open their emails and click on seemingly benign links.

The latest email trend involves attackers who claim to be from the Center for Disease Control and Prevention, purporting to have emergency information about COVID-19. This is typical of a recent trend we’re calling ‘fearware’: cyber-criminals exploit a collective sense of fear and urgency, and coax users into clicking a malicious attachment or link. While the tactic is common, the actual campaigns contain terms and content that’s unique. There are a few patterns in the emails we’ve seen, but none reliably predictable enough to create hard and fast rules that will stop emails with new wording without causing false positives.

For example, looking for the presence of “CDC” in the email sender would easily fail when the emails begin to use new wording, like “WHO”. We’ve also seen a mismatch of links and their display text – with display text that reads “https://cdc.gov/[random-path]” while the actual link is a completely arbitrary URL. Looking for a pattern match on this would likely lead to false positives and would serve as a weak indicator at best.

The majority of these emails, especially the early ones, passed most of our customers’ existing defenses including Mimecast, Proofpoint, and Microsoft’s ATP, and were approved to be delivered directly to the end user’s inbox. Fortunately, these emails were immediately identified and actioned by Antigena Email, Darktrace’s Autonomous Response technology for the inbox.

Gateways: The Current Approach

Most organizations employ Secure Email Gateways (SEGs), like Mimecast or Proofpoint, which serve as an inline middleman between the email sender and the recipient’s email provider. SEGs have largely just become spam-detection engines, as these emails are obvious to spot when seen at scale. They can identify low-hanging fruit (i.e. emails easily detectable as malicious), but they fail to detect and respond when attacks become personalized or deviate even slightly from previously-seen attacks.

Figure 1: A high-level diagram depicting an Email Secure Gateway’s inline position.

SEGs tend to use lists of ‘known-bad’ IPs, domains, and file hashes to determine an email’s threat level – inherently failing to stop novel attacks when they use IPs, domains, or files which are new and have not yet been triaged or reported as malicious.

When advanced detection methods are used in gateway technologies, such as anomaly detection or machine learning, these are performed after the emails have been delivered, and require significant volumes of near-identical emails to trigger. The end result is very often to take an element from one of these emails and simply deny-list it.

When a SEG can’t make the determination on these factors, they may resort to a technique known as sandboxing, which creates an isolated environment for testing links and attachments seen in emails. Alternatively, they may turn to basic levels of anomaly detection that are inadequate due to their lack of context of data outside of emails. For sandboxing, most advanced threats now typically employ evasion techniques like an activation time that waits until a certain date before executing. When deployed, the sandboxing attempts see a harmless file, not recognizing the sleeping attack waiting within.

Figure 2: This email was registered only 2 hours prior to an email we processed.

Taking a sample COVID-19 email seen in a Darktrace customer’s environment, we saw a mix of domains used in what appears to be an attempt to avoid pattern detection. It would be improbable to have the domains used on a list of ‘known-bad’ domains anywhere at the time of the first email, as it was received a mere two hours after the domain was registered.

Figure 3: While other defenses failed to block these emails, Antigena Email immediately marked them as 100% unusual and held them back from delivery.

Antigena Email sits behind all other defenses, meaning we only see emails when those defenses fail to block a malicious email or deem an email is safe for delivery. In the above COVID-19 case, the first 5 emails were marked by MS ATP with a spam confidence score of 1, indicating Microsoft scanned the email and it was determined to be clean – so Microsoft took no action whatsoever.

The Cat and Mouse Game

Cyber-criminals are permanently in flux, quickly moving to outsmart security teams and bypass current defenses. Recognizing email as the easiest entry point into an organization, they are capitalizing on the inadequate detection of existing tools by mass-producing personalized emails through factory-style systems that machine-research, draft, and send with minimal human interaction.

Domains are cheap, proxies are cheap, and morphing files slightly to change the entire fingerprint of a file is easy – rendering any list of ‘known-bads’ as outdated within seconds.

Cyber AI: The New Approach

A new approach is required that relies on business context and an inside-out understanding of a corporation, rather than analyzing emails in isolation.

An Immune System Approach

Darktrace’s core technology uses AI to detect unusual patterns of behavior in the enterprise. The AI is able to do this successfully by following the human immune system’s core principles: develop an innate sense of ‘self’, and use that understanding to detect abnormal activity indicative of a threat.

In order to identify threats across the entire enterprise, the AI is able to understand normal patterns of behavior beyond just the network. This is crucial when working towards a goal of full business understanding. There’s a clear connection between activity in, for example, a SaaS application and a corresponding network event, or an event in the cloud and a corresponding event elsewhere within the business.

There’s an explicit relationship between what people do on their computers and the emails they send and receive. Having the context that a user has just visited a website before they receive an email from the same domain lends credibility to that email: it’s very common to visit a website, subscribe to a mailing list, and then receive an email within a few minutes. On the contrary, receiving an email from a brand-new sender, containing a link that nobody in the organization has ever been to, lends support to the fact that the link is likely no good and that perhaps the email should be removed from the user’s inbox.

Enterprise-Wide Context

Darktrace’s Antigena Email extends this interplay of data sources to the inbox, providing unique detection capabilities by leveraging full business context to inform email decisions.

The design of Antigena Email provides a fundamental shift in email security – from where the tool sits to how it understands and processes data. Unlike SEGs, which sit inline and process emails only as they first pass through and never again, Antigena Email sits passively, ingesting data that is journaled to it. The technology doesn’t need to wait until a domain is fingerprinted or sandboxed, or until it is associated with a campaign that has a famous name and all the buzz.

Antigena Email extends its unique position of not sitting inline to email re-assessment, processing emails millions of times instead of just once, enabling actions to be taken well after delivery. A seemingly benign email with popular links may become more interesting over time if there’s an event within the enterprise that was determined to have originated via an email, perhaps when a trusted site becomes compromised. While Antigena Network will mitigate the new threat on the network, Antigena Email will neutralize the emails that contain links associated with those found in the original email.

Figure 4: Antigena Email sits passively off email providers, continuously re-assessing and issuing updated actions as new data is introduced.

When an email first arrives, Antigena Email extracts its raw metadata, processes it multiple times at machine speed, and then many millions of times subsequently as new evidence is introduced (typically based on events seen throughout the business). The system corroborates what it is seeing with what it has previously understood to be normal throughout the corporate environment. For example, when domains are extracted from envelope information or links in the email body, they’re compared against the popularity of the domain on the company’s network.

Figure 5: The link above was determined to be 100% rare for the enterprise.

Dissecting the above COVID-19 linked email, we can extract some of the data made available in the Antigena Email user interface to see why Darktrace thought the email was so unusual. The domain in the ‘From’ address is rare, which is supplemental contextual information derived from data across the customer’s entire digital environment, not limited to just email but including network data as well. The emails’ KCE, KCD, and RCE indicate that it was the first time the sender had been seen in any email: there had been no correspondence with the sender in any way, and the email address had never been seen in the body of any email.

Figure 6: KCE, KCD, and RCE scores indicate no sender history with the organization.

Correlating the above, Antigena Email deemed these emails 100% anomalous to the business and immediately removed them from the recipients’ inboxes. The platform did this for the very first email, and every email thereafter – not a single COVID-19-based email got by Antigena Email.

Conclusion

Cyber AI does not distinguish ‘good’ from ‘bad’; rather whether an event is likely to belong or not. The technology looks only to compare data with the learnt patterns of activity in the environment, incorporating the new email (alongside its own scoring of the email) into its understanding of day-to-day context for the organization.

By asking questions like “Does this email appear to belong?” or “Is there an existing relationship between the sender and recipient?”, the AI can accurately discern the threat posed by a given email, and incorporate these findings into future modelling. A model cannot be trained to think just because the corporation received a higher volume of emails from a specific sender, these emails are all of a sudden considered normal for the environment. By weighing human interaction with the emails or domains to make decisions on math-modeling reincorporation, Cyber AI avoids this assumption, unless there’s legitimate correspondence from within the corporation back out to the sender.

The inbox has traditionally been the easiest point of entry into an organization. But the fundamental differences in approach offered by Cyber AI drastically increase Antigena Email’s detection capability when compared with gateway tools. Customers with and without email gateways in place have therefore seen a noticeable curbing of their email problem. In the continuous cat-and-mouse game with their adversaries, security teams augmenting their defenses with Cyber AI are finally regaining the advantage.

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
Dan Fein
VP, Product

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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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