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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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December 22, 2025

The Year Ahead: AI Cybersecurity Trends to Watch in 2026

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Introduction: 2026 cyber trends

Each year, we ask some of our experts to step back from the day-to-day pace of incidents, vulnerabilities, and headlines to reflect on the forces reshaping the threat landscape. The goal is simple:  to identify and share the trends we believe will matter most in the year ahead, based on the real-world challenges our customers are facing, the technology and issues our R&D teams are exploring, and our observations of how both attackers and defenders are adapting.  

In 2025, we saw generative AI and early agentic systems moving from limited pilots into more widespread adoption across enterprises. Generative AI tools became embedded in SaaS products and enterprise workflows we rely on every day, AI agents gained more access to data and systems, and we saw glimpses of how threat actors can manipulate commercial AI models for attacks. At the same time, expanding cloud and SaaS ecosystems and the increasing use of automation continued to stretch traditional security assumptions.

Looking ahead to 2026, we’re already seeing the security of AI models, agents, and the identities that power them becoming a key point of tension – and opportunity -- for both attackers and defenders. Long-standing challenges and risks such as identity, trust, data integrity, and human decision-making will not disappear, but AI and automation will increase the speed and scale of the cyber risk.  

Here's what a few of our experts believe are the trends that will shape this next phase of cybersecurity, and the realities organizations should prepare for.  

Agentic AI is the next big insider risk

In 2026, organizations may experience their first large-scale security incidents driven by agentic AI behaving in unintended ways—not necessarily due to malicious intent, but because of how easily agents can be influenced. AI agents are designed to be helpful, lack judgment, and operate without understanding context or consequence. This makes them highly efficient—and highly pliable. Unlike human insiders, agentic systems do not need to be socially engineered, coerced, or bribed. They only need to be prompted creatively, misinterpret legitimate prompts, or be vulnerable to indirect prompt injection. Without strong controls around access, scope, and behavior, agents may over-share data, misroute communications, or take actions that introduce real business risk. Securing AI adoption will increasingly depend on treating agents as first-class identities—monitored, constrained, and evaluated based on behavior, not intent.

-- Nicole Carignan, SVP of Security & AI Strategy

Prompt Injection moves from theory to front-page breach

We’ll see the first major story of an indirect prompt injection attack against companies adopting AI either through an accessible chatbot or an agentic system ingesting a hidden prompt. In practice, this may result in unauthorized data exposure or unintended malicious behavior by AI systems, such as over-sharing information, misrouting communications, or acting outside their intended scope. Recent attention on this risk—particularly in the context of AI-powered browsers and additional safety layers being introduced to guide agent behavior—highlights a growing industry awareness of the challenge.  

-- Collin Chapleau, Senior Director of Security & AI Strategy

Humans are even more outpaced, but not broken

When it comes to cyber, people aren’t failing; the system is moving faster than they can. Attackers exploit the gap between human judgment and machine-speed operations. The rise of deepfakes and emotion-driven scams that we’ve seen in the last few years reduce our ability to spot the familiar human cues we’ve been taught to look out for. Fraud now spans social platforms, encrypted chat, and instant payments in minutes. Expecting humans to be the last line of defense is unrealistic.

Defense must assume human fallibility and design accordingly. Automated provenance checks, cryptographic signatures, and dual-channel verification should precede human judgment. Training still matters, but it cannot close the gap alone. In the year ahead, we need to see more of a focus on partnership: systems that absorb risk so humans make decisions in context, not under pressure.

-- Margaret Cunningham, VP of Security & AI Strategy

AI removes the attacker bottleneck—smaller organizations feel the impact

One factor that is currently preventing more companies from breaches is a bottleneck on the attacker side: there’s not enough human hacker capital. The number of human hands on a keyboard is a rate-determining factor in the threat landscape. Further advancements of AI and automation will continue to open that bottleneck. We are already seeing that. The ostrich approach of hoping that one’s own company is too obscure to be noticed by attackers will no longer work as attacker capacity increases.  

-- Max Heinemeyer, Global Field CISO

SaaS platforms become the preferred supply chain target

Attackers have learned a simple lesson: compromising SaaS platforms can have big payouts. As a result, we’ll see more targeting of commercial off-the-shelf SaaS providers, which are often highly trusted and deeply integrated into business environments. Some of these attacks may involve software with unfamiliar brand names, but their downstream impact will be significant. In 2026, expect more breaches where attackers leverage valid credentials, APIs, or misconfigurations to bypass traditional defenses entirely.

-- Nathaniel Jones, VP of Security & AI Strategy

Increased commercialization of generative AI and AI assistants in cyber attacks

One trend we’re watching closely for 2026 is the commercialization of AI-assisted cybercrime. For example, cybercrime prompt playbooks sold on the dark web—essentially copy-and-paste frameworks that show attackers how to misuse or jailbreak AI models. It’s an evolution of what we saw in 2025, where AI lowered the barrier to entry. In 2026, those techniques become productized, scalable, and much easier to reuse.  

-- Toby Lewis, Global Head of Threat Analysis

Conclusion

Taken together, these trends underscore that the core challenges of cybersecurity are not changing dramatically -- identity, trust, data, and human decision-making still sit at the core of most incidents. What is changing quickly is the environment in which these challenges play out. AI and automation are accelerating everything: how quickly attackers can scale, how widely risk is distributed, and how easily unintended behavior can create real impact. And as technology like cloud services and SaaS platforms become even more deeply integrated into businesses, the potential attack surface continues to expand.  

Predictions are not guarantees. But the patterns emerging today suggest that 2026 will be a year where securing AI becomes inseparable from securing the business itself. The organizations that prepare now—by understanding how AI is used, how it behaves, and how it can be misused—will be best positioned to adopt these technologies with confidence in the year ahead.

Learn more about how to secure AI adoption in the enterprise without compromise by registering to join our live launch webinar on February 3, 2026.  

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December 22, 2025

Why Organizations are Moving to Label-free, Behavioral DLP for Outbound Email

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Why outbound email DLP needs reinventing

In 2025, the global average cost of a data breach fell slightly — but remains substantial at USD 4.44 million (IBM Cost of a Data Breach Report 2025). The headline figure hides a painful reality: many of these breaches stem not from sophisticated hacks, but from simple human error: mis-sent emails, accidental forwarding, or replying with the wrong attachment. Because outbound email is a common channel for sensitive data leaving an organization, the risk posed by everyday mistakes is enormous.

In 2025, 53% of data breaches involved customer PII, making it the most commonly compromised asset (IBM Cost of a Data Breach Report 2025). This makes “protection at the moment of send” essential. A single unintended disclosure can trigger compliance violations, regulatory scrutiny, and erosion of customer trust –consequences that are disproportionate to the marginal human errors that cause them.

Traditional DLP has long attempted to mitigate these impacts, but it relies heavily on perfect labelling and rigid pattern-matching. In reality, data loss rarely presents itself as a neat, well-structured pattern waiting to be caught – it looks like everyday communication, just slightly out of context.

How data loss actually happens

Most data loss comes from frustratingly familiar scenarios. A mistyped name in auto-complete sends sensitive data to the wrong “Alex.” A user forwards a document to a personal Gmail account “just this once.” Someone shares an attachment with a new or unknown correspondent without realizing how sensitive it is.

Traditional, content-centric DLP rarely catches these moments. Labels are missing or wrong. Regexes break the moment the data shifts formats. And static rules can’t interpret the context that actually matters – the sender-recipient relationship, the communication history, or whether this behavior is typical for the user.

It’s the everyday mistakes that hurt the most. The classic example: the Friday 5:58 p.m. mis-send, when auto-complete selects Martin, a former contractor, instead of Marta in Finance.

What traditional DLP approaches offer (and where gaps remain)

Most email DLP today follows two patterns, each useful but incomplete.

  • Policy- and label-centric DLP works when labels are correct — but content is often unlabeled or mislabeled, and maintaining classification adds friction. Gaps appear exactly where users move fastest
  • Rule and signature-based approaches catch known patterns but miss nuance: human error, new workflows, and “unknown unknowns” that don’t match a rule

The takeaway: Protection must combine content + behavior + explainability at send time, without depending on perfect labels.

Your technology primer: The three pillars that make outbound DLP effective

1) Label-free (vs. data classification)

Protects all content, not just what’s labeled. Label-free analysis removes classification overhead and closes gaps from missing or incorrect tags. By evaluating content and context at send time, it also catches misdelivery and other payload-free errors.

  • No labeling burden; no regex/rule maintenance
  • Works when tags are missing, wrong, or stale
  • Detects misdirected sends even when labels look right

2) Behavioral (vs. rules, signatures, threat intelligence)

Understands user behavior, not just static patterns. Behavioral analysis learns what’s normal for each person, surfacing human error and subtle exfiltration that rules can’t. It also incorporates account signals and inbound intel, extending across email and Teams.

  • Flags risk without predefined rules or IOCs
  • Catches misdelivery, unusual contacts, personal forwards, odd timing/volume
  • Blends identity and inbound context across channels

3) Proprietary DSLM (vs. generic LLM)

Optimized for precise, fast, explainable on-send decisions. A DSLM understands email/DLP semantics, avoids generative risks, and stays auditable and privacy-controlled, delivering intelligence reliably without slowing mail flow.

  • Low-latency, on-send enforcement
  • Non-generative for predictable, explainable outcomes
  • Governed model with strong privacy and auditability

The Darktrace approach to DLP

Darktrace / EMAIL – DLP stops misdelivery and sensitive data loss at send time using hold/notify/justify/release actions. It blends behavioral insight with content understanding across 35+ PII categories, protecting both labeled and unlabeled data. Every action is paired with clear explainability: AI narratives show exactly why an email was flagged, supporting analysts and helping end-users learn. Deployment aligns cleanly with existing SOC workflows through mail-flow connectors and optional Microsoft Purview label ingestion, without forcing duplicate policy-building.

Deployment is simple: Microsoft 365 routes outbound mail to Darktrace for real-time, inline decisions without regex or rule-heavy setup.

A buyer’s checklist for DLP solutions

When choosing your DLP solution, you want to be sure that it can deliver precise, explainable protection at the moment it matters – on send – without operational drag.  

To finish, we’ve compiled a handy list of questions you can ask before choosing an outbound DLP solution:

  • Can it operate label free when tags are missing or wrong? 
  • Does it truly learn per user behavior (no shortcuts)? 
  • Is there a domain specific model behind the content understanding (not a generic LLM)? 
  • Does it explain decisions to both analysts and end users? 
  • Will it integrate with your label program and SOC workflows rather than duplicate them? 

For a deep dive into Darktrace’s DLP solution, check out the full solution brief.

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About the author
Carlos Gray
Senior Product Marketing Manager, Email
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