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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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May 27, 2026

How to Evaluate AI Vendors: 5 Key categories for AI Adoption

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Understanding the AI buyers’ market

AI adoption has become a central topic of discussion in boardrooms, drawing growing interest from business leaders. Ultimately, organizations hope that an investment in AI technology will have tremendous returns. However, the process of buying an AI solution is not as straight forward as it appears on the surface.  

While business leaders may be eager to improve productivity across their operations, practitioners responsible for evaluating and selecting AI solutions may not always have the visibility or technical understanding needed to make the right decisions for their business. What is typically marketed as a holistic solution to their most critical problems is usually followed by uncertainty when AI tools are finally operationalized in real environments.

This guide is intended to support security leaders who are under growing pressure to adopt AI tools while navigating complex terminology, vendor claims, and increasingly crowded buying cycles. Ultimately, the goal is to help organizations evaluate and adopt AI in a safe, effective, and well-governed way. To support this, we’ve structured the evaluation framework across five key categories:

  1. Governance, safety, and data controls
  1. Data gathering and training
  1. Model and technique choice
  1. Performance and accuracy validation    
  1. Interpretability, adjustability, and transparency    

What buying AI looks like in cybersecurity

While investing in AI can bring immense benefits to your security team, first-time buyers of AI cybersecurity solutions may not know where to start. They will have to determine the type of tool they want, know the options available, and evaluate vendors. Research and understanding are critical to ensure purchases are worth the investment.  

With acceleration in AI adoption, accompanied by the recent boom in agentic AI and autonomous agents, CISOs must look “beneath the hood" of these tools to understand how they work, how they are governed, and to ensure the system is secure and compliant with internal policies.

Challenges in the AI buyers’ marketplace  

The AI security software market is buzzing with hype and flashy promises, which, understandably, needs to be addressed with due diligence. Potential buyers, especially in the cybersecurity space, are hesitant when it comes to allowing AI autonomous capabilities across their workflows, and a lack of vendor transparency can exacerbate those feelings.  

Reinforcing this sentiment, research from this year's Darktrace’s State of AI Cybersecurity report shows where confidence and hesitancy emerge amongst potential buyers. On the one hand, security professionals agree that they have good visibility into the logic and reasoning processes their AI solutions use. However, they lack the explainability and trust to allow AI to take independent remedial action.

  • 89% say they have good visibility into the reasoning behind the outputs generated by AI solutions
  • 92% say they need to understand how a defensive AI tool makes decisions before they can trust it
  • Only 14% say they allow AI to act independently, performing autonomous actions without human approval
  • 74% say they are limiting the autonomy of AI taking action in their SOC until explainability improves

Given the desire for trust and explainability we are seeing from buyers, it's important for them to be equipped with the right questions to ask vendors during an assessment or POV of AI tools in order to demystify marketing hype from real operational outcomes.

Below is a list of categories in which buyers can assess AI vendors or AI Service Providers (AISPs) to help reach safe adoption and maximize their ROI.  

5 categories of AI vendor assessment

Darktrace groups these AI-related questions into 5 categories: governance, data and training, model and technique choice, performance validation, and interpretability and adjustability. By asking questions regarding each of these 5 categories, buyers can gain a deeper understanding of how an AISP’s systems work and whether they suit their business requirements.

Governance, safety, and data controls

Governance of AI systems is critical for all AISPs. Whether their platform is based around a single model, or is a more complex, composite AI solution, strong governance is essential to ensure the system is safe, robust, and reliable.

A simple question you could ask is:

What AI governance policies and frameworks do you follow, and/or certifications do you currently maintain?

For more questions you can ask vendors, download the full guide here.

Darktrace is certified to the ISO/IEC 42001 standard, the world’s first AI Management System (AIMS) standard. ISO/IEC 42001 addresses the unique ethical and technical challenges AI poses by setting out a structured way to manage risks such as transparency, accuracy, and misuse. This includes a commitment to ethical AI development, and effective management and monitoring of AI systems both prior to and continually after release.

Data gathering and training

Accurate, meaningful, and unbiased data gathering is the first important step in producing any AI system. An AI model trained using inaccurate, unbalanced, or poor-quality training data will fail to perform optimally.

To alleviate concerns regarding training data quality, a question you could ask is:

What steps do you take to prevent bias in your AI models and training data?

For more questions, download the full guide here.

AISPs should be able to provide information about the steps taken, workflows followed, and auditing performed to reduce AI bias where appropriate. While it’s sometimes impossible to fully remove bias from an AI model, appropriate actions should be taken to mitigate or reduce bias where relevant.

Model and technique choice

Different AI techniques are optimal for different tasks. For example, research from Gartner suggests that relying on a single “one-size-fits-all" model can lead to data gaps, especially in highly specialized domains.

To achieve more accurate and robust AI solutions, AI leaders should move beyond using just one model or technique, embrace composite AI practices, and adopt a holistic AI system perspective.

A straightforward question you could ask is simply:

What type(s) of AI model(s) do you utilize in your solution?

For more questions, download the full guide here.

While specific detailed information about custom systems used by AISPs is likely proprietary, buyers should expect vendors to be able to provide an overview of the broad techniques used. This will allow you as a buyer to determine if the type of model is appropriate for your use case.

Performance and accuracy validation  

Testing and evaluation of performance is essential for all AI systems. Performance analysis should be performed both before release and continually after release to identify potential data or model drift.  

A question you could ask to understand an AISPs testing workflow is:

How do you audit, test, evaluate, verify, and validate your AI model outputs?

For more questions, download the full guide here.

Testing workflows will likely vary depending on the type of model – measurements relevant to one system may not always be relevant to others. Assessment of systems should also extend beyond these standard accuracy and robustness tests, and should also feature physical performance, such as latency and resource consumption.  

Interpretability, adjustability, and transparency  

AI systems are typically a black box, simply providing an output without an explanation of how that output was attained. Interpretability and transparency are critical to ensure that both SOC teams and end-users trust the outputs of a system to be accurate and meaningful.

A question you could ask is:

How do you promote a trust relationship between human analysts and AI outputs?

For more questions, download the full guide here.

In the context of cybersecurity, trust and interpretability are even more essential. This is particularly relevant for generative AI-based systems (including most AI Agents), where the risk of hallucination can reduce trust in responses.

Cybersecurity systems often need to perform autonomous actions to block incoming threats – an email filtering system may hold potentially dangerous emails; a firewall may block malicious inbound connections. If SOC teams can’t trust these systems to perform accurately, these systems may be limited or disabled, critically reducing their defensive power.

Darktrace as an AI-native cybersecurity vendor

Darktrace has been building and applying AI in cybersecurity for over a decade, developing its capabilities alongside an increasingly complex and fast‑moving threat landscape. This experience has resulted in a mature, multi-layered approach to AI, which continuously learns the normal patterns of each organization to understand behavior, interpret context, and identify meaningful deviations — without relying on predefined rules or known attack signatures. Over time, this has enabled a proven behavioral understanding that helps uncover subtle signals of risk that may otherwise be missed.

With the backing of our ISO/IEC 42001 certification, stakeholders, customers, and partners can be confident that Darktrace is responsibly, ethically, and safely developing its AI systems, and managing the use of AI in day-to-day operations in a compliant and secure manner.  

Explore the principles behind Darktrace’s responsible AI approach, informed by collaboration with global experts in academia and governments, detailing how accountability, explainability, and continuous validation are built into its cybersecurity technology.

How Darktrace secures AI systems

Darktrace now brings these capabilities to monitor and respond to risk generated from AI systems across organizations with Darktrace / SECURE AI. This solution analyzes how prompts, agents, and systems are used within the context of each organization, bringing every AI interaction into a single view. This unique approach helps teams understand intent, assess risk, protect sensitive data, and enforce policy across both human and AI agent activity.

Stay up to date

Sign up for the Secure AI Readiness Program here: This gives you exclusive access to the latest news on the latest AI threats, updates on emerging approaches shaping AI security, and insights into the latest innovations, including Darktrace’s ongoing work in this area.

Ready to talk with a Darktrace expert on securing AI? Register here to receive practical guidance on the AI risks that matter most to your business, paired with clarity on where to focus first across governance, visibility, risk reduction, and long-term readiness.  

Further Reading on AI in cybersecurity

When deciding to invest in an AI solution, it’s important to understand what this means for you and your organization. The questions presented here are only a starting point in understanding an AI solution and whether it is appropriate for your use case.  

Gain deeper knowledge on applications of AI in cybersecurity and Darktrace’s multi-layered AI in the AI Arsenal White Paper.

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May 26, 2026

Journey of a Threat: How Multi-Layered AI Works in Darktrace / EMAIL

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Darktrace / EMAIL is an implementation of the Darktrace methodology – a multi-layered AI system built into a single product. As with other Darktrace products, Darktrace / EMAIL learns the expected behaviours of an organization and its employees to identify novel threats and anomalous activity.

The diagram below represents the architecture of Darktrace / EMAIL’s multi-layered AI: a structured visualization of how intelligence is built, step by step, from raw data to actionable insight. Each layer plays a distinct role, feeding into the next: collecting data, understanding behaviour, analysing intent, making decisions, and presenting clear outcomes.

It all starts with an email

In this blog, we’ll follow a malicious email as it passes through the Darktrace / EMAIL system, showing exactly what happens as it travels through each layer of the pyramid, from basic data extraction to AI-powered metric creation, and finally deciding on any autonomous actions.

Let’s take this example email. As an end-user, you can see that this is an obvious extortion attempt where an adversary is threatening legal action if money isn’t paid within 24 hours, but how does Darktrace figure that out?

Part 1: Data Gathering

Processing of an email begins on point-of-transit for all inbound, outbound, or lateral emails. The first step is to extract information directly. This includes taking information from the headers (such as sending and receiving addresses, sender IP address, routing, and authentication protocols), as well as extraction of raw HTML and CSS data from the email itself.

This directly extracted information only allows for immediate surface level analysis, such as identifying signature-based attacks (known malicious addresses / domains), but is insufficient for identifying novel threats, complex attacks, or potential email or vendor compromise. This is where Darktrace’s AI analysis shines.

In this example, the SPF, DKIM, and DMARC authentication all passed successfully, showing that even malicious emails can still bypass these signature-based checks. Even with this success, Darktrace will continue to analyse the email.

Diving deeper into the technical information, we can see further information extracted from the headers, including aggregations from the header information, historical calculations such as the frequency and volume of emails to and from a particular domain, and much more.

Part 2: Social Graphing

Social Graphing involves the analysis of sending and receiving behaviours of different mailboxes to create peer-groups. Mailboxes who often send and receive to and from the same mailboxes, or exhibit other correlated behaviours, will be clustered together using a collection of unsupervised AI clustering systems. These groups may represent uses in the same teams who perform similar activity, groups of external facing mailboxes which often receive unsolicited emails, or groups of VIP users (such as C-suite or executives).

Social graphing is an essential component of Darktrace’s pattern of life analysis. This clustering allows Darktrace to understand the responsibilities of individuals – for example, behaviours which are anomalous for one group of users may be completely expected of another group.

In our example, the email was sent to 3 different users within the organization. As part of the social graphing, an “Association Anomaly” is calculated which indicates the likelihood that these users would receive emails from this user or domain, based on historical patterns.

Part 3: Metric Calculation

Metrics are calculated for every email, representing more complex characteristics of an email which can’t be directly extracted. Darktrace / EMAIL features over 1000 unique metrics, calculated both algorithmically and using an ensemble of AI systems.

Algorithmically calculated (non-AI) metrics include further historical calculations, and counts of features such as code blocks, and hidden text, to name a few.

AI-driven metrics include Inducement Classification which uses Natural Language Processing to identify potential phishing, solicitation, or extortion attempts; Named Entity Recognition to identify PII and other sensitive data within an email to support Data Loss Prevention; and many more.

We can follow our example email through this process and view the outcome of these metric calculations. Looking at the language metrics for this email, we can see that our email has reported a high extortion inducement, along with identification of banking information and language indicating urgency.

Part 4: Evaluation and Combination Engine (models)

Once all metrics have been calculated for an email, it gets sent to an evaluation and combination engine where the metrics are compared against blocks of logic to determine if an email contains a threat. One key model which alerted for this example message was a model to tag and block extortion attempts.

Since our example email has a high inducement score for extortion, along the presence of a bitcoin wallet address in the message, this model alerts. When a model in the engine is activated, actions are taken – in this case adding a tag to the email to flag it as extortion in the console and hold the email to prevent it from reaching the end-user mailbox.

Part 5: Meta-Modelling and Actions

Once the models have been run, the actions are taken against the email. If the email hasn’t been blocked or held, this is the point where it will reach the end-user's mailbox.

In the Darktrace / EMAIL UI, all actions models which alerted for an email and actions taken as a result can be seen. At the top of this page, you can see the alert indicating an extortion attempt along with the action to hold the message.

Alongside this, a meta-classifier is used to calculate an overall anomaly score for each email, based on how much the email differs from the pattern of life for the user. The score of the email is boosted by any actions that have taken place.

Part 6: Campaign Clustering

All emails are passed through the Darktrace / EMAIL campaign clustering system. This system creates clusters based on related features within the emails to identify groups of emails with the same sender or intent.

In our case, the email was identified as part of a campaign, alongside other emails which were also identified as extortion attempts against a small group of recipients.

Email campaigns may have additional actions applied to them if the campaign is deemed malicious, and in this case, you can see that the autonomous response was to hold all emails in the campaign. This means that if an email manages to avoid being blocked in the evaluation and combination engine but gets identified as part of the campaign, the hold action will be applied to it retroactively.

Part 7: Cyber AI Analyst

Darktrace’s Cyber AI Analyst presents key information and anomaly indicators for each email, such as further information about authentication, specific metrics, or other identified anomalies and mismatches.

Cyber AI Analyst can also utilize data from Darktrace / EMAIL to enhance its investigation of incidents from other Darktrace products, correlating relevant information to build a fuller picture. More information about the Cyber AI Analyst is available in the Darktrace AI Arsenal.

Part 8: Data Presentation (UI)

Once all processing has taken place against the email, it is presented in the Darktrace / EMAIL UI. Here, members of the SOC team can investigate incidents and anomalies, interact with malicious emails to see why they were blocked, and much more.

Our email stands out here with its 100 anomaly score. Every email which passes through a Darktrace / EMAIL will undergo the same thorough and rigorous analysis to identify potential risks, apply autonomous actions where required, and will ultimately be assigned a score to be displayed here. By providing a single overall score in the UI, rather than presenting emails in full, Darktrace / EMAIL allows SOC teams to more easily identify which emails are most important to investigate, increasing efficiency and reducing alert fatigue.

Take the next step

Many email security tools on the market that claim to be AI-driven are in fact bolting AI onto attack-centric approaches, which rely on automating the identification of known threats. These approaches struggle, and will continue to struggle, with adapting to novel, AI-generated threats.

By analyzing every email within its deeply integrated, multi-layered AI system, Darktrace / EMAIL is able to identify the subtle threats that others miss. This depth not only improves detection accuracy, but enables confident, autonomous action, giving security teams clearer insight into AI outcomes and greater control while supporting users.

For a full deep dive into each stage of the AI system, check out the white paper: A Guide to the Multi-Layered AI in Darktrace / EMAIL

Learn more about securing AI in your enterprise.

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Jamie Bali
Technical Author (AI) Developer
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