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July 3, 2020

Academic Institution Loses $60k to Email Attack

An academic institution turned to Darktrace after an email attack slipped through their existing security stack and cost them over $60,000.
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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03
Jul 2020

Introduction

Many organizations turn to AI to augment their email security only after a damaging attack serves as a wake-up call. Such was the case recently with an academic institution in the APAC region. The organization felt fully protected at the time, with spam protection, URL protection, and the full Mimecast package across the email realm. However, it was interested in understanding how Cyber AI might defend its inbox, and scheduled a conversation to learn more.

Two days before that conversation was due to take place, the company was hit by a Business Email Compromise. An attacker had taken over an internal Microsoft 365 account and sent a fraudulent invoice to the organization’s accounts department. The invoice, which contained subtly edited bank details, claimed to be from Siemens, one of the world’s leading automation technology companies. Given that Siemens was an established supplier, the attack succeeded – and the academic institution unwittingly paid over $60,000 into an attacker’s bank account.

The incident alerted this organization not only to the scale and severity of email attacks, but also the limitations in its existing security tools. The security team swiftly deployed Antigena Email, and the AI’s ability to neutralize the advanced attacks missed by other tools was immediately realized when the attacker tried again a week later.

On this occasion, with the AI now in place, unusual behavior on the compromised SaaS account together with the suspicious email activity caused several Darktrace models to fire, culminating in a 73% anomaly score and the decision to autonomously hold back the offending email. The below details the timeline of this attack, and how Darktrace was able to identify an attack where other security tools failed.

Patient Zero: the initial compromise

Darktrace first detected something was amiss when a SaaS login was seen from an unusual IP address located in the UAE.

Tue April 21 04:15:40 (local time)

It then noticed a behavior commonly associated with Business Email Compromise – the creation of an inbox processing rule so that any incoming emails from the vendor would be deleted and redirected to the threat-actor.

Tue April 21st 05:04:21

Wed April 22nd 16:51:14

Figure 1: Darktrace detecting the anomalous mailbox rule, indicating a 97-100% anomalous activity

This initial compromise led to a very targeted spear phishing campaign. The attacker found an authentic email chain regarding an invoice from the domain siemens.com. Using the trusted supplier’s reputation, they copied the exact format of the invoice and then created a spoofed domain ‘siemesm.com’, intending to target the accounts team at the organization with a fresh invoice – but with one important detail changed – the bank details.

The attacker was careful. Before launching the attack, they sent a test email to the compromised account to ensure it was getting through. As seen below, this alerted Antigena Email with a 38% anomaly score.

The fraudulent invoice

The following morning, the attacker set up some fake correspondence between the newly created account and Patient Zero, before looping in the accounts team with a new request – this time, asking for $78,000. Again, the exchange appeared legitimate: from a well-known supplier, and with the apparent ratification of a trusted colleague.

Figure 2: Antigena Email detecting the anomalous emails, with the red hold icon indicating that it held the emails back from the recipient

Here, we can see Antigena Email growing gradually more suspicious of this unusual behavior over time, with the highlighted ‘hold’ icon indicating that Antigena Email prevented the two offending emails from being delivered. The high anomaly score was influenced not only by the lack of previous correspondence between the two email users, but also the email rules that were made on the account itself the previous day. Furthermore, Cyber AI recognized the email as a fake reply: not a direct response to the email, but one which attempted to replicate it by copying and pasting correspondence from a separate email chain.

Realizing their initial attack had failed, the attacker then leveraged a technique known as ‘island hopping’, harvesting the company-wide contact list, and going on to launch a more generic phishing campaign to dozens of email users across the company – hoping in turn to compromise their accounts.

Figure 3: A selection of the subsequent emails sent from the initially compromised account

Again, Antigena Email deemed every one of these emails to be 100% anomalous and held them back in every case.

Whilst this was a relatively advanced attack with multiple stages, the techniques described above represent nothing exceptional – Antigena Email stops these kinds of attacks on a daily basis, in hundreds of organizations around the globe.

By deploying Cyber AI into their email environments, defenders not only have unrivalled visibility over internal and external mail flow, but the ability to stop targeted and sophisticated attacks, well before they can escalate into a crisis.

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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Email

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July 24, 2026

Darktrace / EMAIL Expands Behavioral Defense Across Email and Collaboration Workflows

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Email and collaboration tools do more than carry messages. They are where organizations approve payments, share sensitive data, reset credentials, and make thousands of everyday decisions. Increasingly, they are interfaces through which humans direct AI agents in their daily activity. Email, Slack and Teams are high volume, rich with sensitive data, and an easy place to hide malicious activity.

The opportunity isn’t lost on bad actors. Darktrace / EMAIL detected more than 32 million high-confidence phishing emails globally in 2025, and 70% of those messages passed DMARC authentication.  Phishing is increasingly difficult to detect and familiar trust signals alone are not enough. People and security teams need to understand how a message fits the normal behavior of the sender, recipient, and organization. They also need to correlate activity across platforms to spot threats that span multiple channels.

To effectively secure against today’s evolved threats, security teams need to act at two levels: they need to help each employee make a safer decision ‘in the moment’, and they need to understand the wider patterns that may expose the business to risk.

Darktrace is introducing four new capabilities in Darktrace / EMAIL to address both challenges. The new features explain suspicious content more clearly to end users, strengthen the capabilities of Darktrace / Adaptive Human Defense with richer guidance, let organizations define their own patterns for detecting sensitive data in messages, and give security teams a process-level view of risk across email and collaboration workflows.

Darktrace / EMAIL Inbox Analysis highlights risky content within your emails

A warning is more useful when it explains what the user should look at. To help do that, we’ve expanded Darktrace / EMAIL’s Inbox Analysis Add-In to highlight potentially dangerous content within the body of emails that Darktrace / EMAIL flags as potentially suspicious or high risk.  

The add-in can highlight language designed to create urgency, financial references, requests for payment, suspicious links, and content that is unusual for the sender. Each highlighted element includes a pop up that explains why it may be suspicious. Instead of asking an employee to accept a verdict without context, the analysis helps them examine the message and make a more informed decision.

Enhanced Just-In-Time Training Banners in Darktrace / Adaptive Human Defense

Enhanced Just-In-Time Training Banners build on the same principle. The banners now include a contextual header, actionable advice, and specific detection context. This gives employees more useful guidance at the point of risk without adding unnecessary information or cognitive load.

Together, the capabilities help turn a warning into a short learning moment. Employees can see what looks unusual, understand what action to take, and build their judgment.

Custom Sensitive Data Detection in Darktrace / EMAIL - Data Loss Prevention

Sensitive data is different for every business. Standard categories such as payment card details or government identifiers matter, but organizations also have their own customer codes, project names, research formats, account structures, and internal identifiers.

Custom Sensitive Data Detection in Darktrace / EMAIL - Data Loss Prevention allows administrators to write custom expressions for the data their organization needs to protect. Matched content can trigger existing model actions and data loss prevention (DLP) workflows, extending Darktrace's DLP capabilities.

This extends data loss detection beyond a fixed library of common data types. Security teams can apply controls to information that is sensitive in the context of their own organization and adapt those controls as the business changes.

Introducing Email and Collaboration Workflow Risk Posture Dashboards

Some of the most important risks are not isolated events. They are repeated ways of working that create an opening for error, misuse, or attack. For example, a payment request may be one suspicious message, but a recurring approval workflow that relies on weak verification is a business process risk.

The new Email and Collaboration Workflow Risk Posture Dashboard analyzes email and collaboration data across Email, Microsoft Teams, Slack and Zoom to provide a process-level view of risk in the organization. These may include financial authorization workflows, sensitive data sharing patterns, and activity that could expose credentials.

The dashboard brings these patterns into a view and provides actionable recommendations. This helps security teams determine where to investigate or strengthen controls, where ownership needs to be clarified, and where the business may need to change a risky process. It gives CISOs a clearer view of how human and communication risk is embedded in everyday operations, not only where individual alerts occur.

Behavior connects the individual decision to the wider risk

These capabilities build on Darktrace’s unique behavioral approach to security. We use Adaptive AI to learn how people and AI normally behave within an organization, creating the context needed to recognize when activity changes.

Within the Darktrace Behavioral Defense Platform, Darktrace / EMAIL helps protect people against phishing, account takeover, data exfiltration, and human risk across email and collaboration tools. The new capabilities extend that protection in both directions. They give employees clearer context for the decision in front of them, while giving security leaders a broader view of the workflows and behavior that create risk across the organization.

The result is not simply more alerts. It is a better understanding of why something is risky, what action to take, and where the organization can reduce risk before a familiar process becomes an easy route for an attacker.

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About the author
Carlos Gray
Senior Product Marketing Manager, Email

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July 24, 2026

When Guardrails Break: Why Securing AI Requires Behavioral Detection and Autonomous Containment

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Bottom line up front: Governance, guardrails, identity controls, and secure development are necessary to secure AI, but they are not sufficient. AI systems are probabilistic, adaptive, and non-deterministic. Therefore, organizations need two additional layers of security:

  1. Behavioral-based detection that can identify when AI begins to act outside its intended purpose; and  
  2. Surgical, explainable autonomous containment that can stop risky activity before it causes material damage.  

That capability depends on multiple specialized AI models working together, not one LLM making every decision.

Organizations are embedding AI into development, business operations, and security workflows faster than most security programs can adapt. The risk is no longer limited to the model. It extends across prompts, data, identities, agents, memory, APIs, tools, permissions, and the trust relationships connecting them.

In my recent blog, Securing AI: Analysis of the Complete Security Stack with Governance and Controls, I outlined a defense-in-depth strategy spanning governance, identity, data security, secure development, runtime detection, autonomous containment, and recovery. The most urgent requirement across that architecture is the ability to understand how AI behaves in practice and contain it when that behavior becomes risky.  

Why non-deterministic systems require behavioral-based detection

Traditional controls remain foundational. Organizations need least privilege, strong identity controls, secure-by-design architecture, data governance, AI inventories, guardrails, testing, and clear boundaries on autonomy.

But deterministic controls, which assume predictable and repeatable behavior, cannot fully secure non-deterministic systems, where the same input may not always produce the same outcome.

AI agents can interpret the same instruction differently, chain individually authorized actions into an unsafe outcome, or pursue a legitimate goal through a method the organization did not anticipate. One of the most recent examples of this is the incident that OpenAI and Hugging Face jointly disclosed, where an autonomous agent escaped its intended testing boundaries and compromised Hugging Face infrastructure.  

An agent may have permission to access data and invoke a tool, but that does not mean every use of that access is appropriate. It is not enough to know whether an action is allowed. Organizations need to know whether it makes sense.

  • Is this normal for this agent?  
  • Is it acting within its intended purpose?  
  • Is it accessing unusual data, invoking an unexpected tool, or beginning to drift?  
  • Do a series of ordinary-looking actions become risky when viewed together?

Behavioral-based detection specific to an environment or organization with an understanding of context and risk enables provides the needed detection engineering for AI systems. It learns normal activity across people, systems, data, devices, and AI agents, then identifies deviations and evaluates their risk, intent, and context. This enables detection of misuse, abuse, compromise, manipulation, and unintended behavior even when no known attack signature or explicit policy violation exists.

Why accuracy is the foundation for SOC optimization

AI will only improve the SOC if it produces accurate, explainable, and actionable outcomes.

If analysts must manually validate every AI-generated finding because they cannot understand the evidence or confidence behind it, automation has not reduced workload. It has moved the workload. False positives increase fatigue. False negatives cause the most risk and damage to organizations. Inaccurate autonomous actions can disrupt critical operations.

Accuracy is therefore more than a model-performance metric. It is the prerequisite for analyst trust, SOC optimization, and safe autonomous response.

That accuracy is unlikely to come from one model.

Generative AI is valuable for natural-language analysis, summarization, and human interaction. But an LLM should not be the sole analytical engine for behavioral-based detection, investigation, risk assessment, and containment. Interpretability and consistency are required for high-consequence security decisions.

A stronger architecture uses multiple specialized AI systems collaboratively:  

  • Behavioral models can establish normal activity.  
  • Unsupervised learning can identify novel anomalies.  
  • Graph analysis can evaluate relationships among agents, identities, systems, and tools.  
  • Other models can correlate events, investigate competing hypotheses, and assess risk.  
  • Semantic models can analyze language where behavior-based language analysis is needed but this can be used in tandem with vector embeddings, graph neural networks, and a variety of other AI systems.

Each model contributes a different analytical perspective. Their outputs can corroborate one another, improving accuracy and creating a more reliable basis for response. The objective is not one model operating as an oracle. It is layered, adaptive intelligence designed to produce decisions the SOC can understand and trust.

Autonomous containment is required to secure autonomous systems

Many SOCs remain hesitant to trust LLM-based agents with autonomous containment. That concern is reasonable. A poorly selected response can isolate the wrong asset, stop a critical workflow, block a legitimate identity, or create more operational damage than the original incident.

But relying exclusively on human response is also not viable.

AI systems can operate at machine speed. They can expose sensitive data, execute workflows, modify records, call tools, or propagate actions across connected systems before an analyst can investigate and intervene. The behavior may be unintentional, the result of an agent optimizing toward a goal, or caused by misuse, compromise, prompt injection, or offensive AI.

Intent affects the investigation. It does not change the need to stop the damage.

Organizations need autonomous response, but it must be surgical and explainable. The objective is not to shut down an entire agent, user, application, or business process whenever an anomaly occurs. It is to interrupt the specific risky behavior: block an unusual connection, constrain a tool call, stop an abnormal data transfer, or temporarily limit an agent when it is performing anomalous, risky activity.  

That buys humans time. It stops the spread, limits damage, and allows the SOC to investigate without unnecessarily disrupting the business.

Layered, Adaptive AI provides a path forward

Darktrace has spent more than a decade researching and operationalizing layered, behavioral, Adaptive AI that learns a specific organization rather than relying only on historic attacks or predefined signatures.

The approach is designed to understand normal behavior, identify anomalous activity, assess its risk, correlate related events, autonomously investigate, and, when necessary, apply targeted containment while normal operations continue.

That sequence matters. Autonomous response cannot simply be added to the end of an LLM workflow. Trusted containment depends on broad visibility, continuous behavioral understanding, multiple analytical techniques, risk and context evaluation, autonomous investigation, explainability, and precise response actions.

This represents a more responsible model for security autonomy: not automation for its own sake, but controlled autonomy built to improve security outcomes and protect business operations.

Security must enable AI adoption

The answer for security teams is not to block AI. Organizations are adopting it to improve productivity, accelerate development, and create new business value.

But innovation without behavioral detection and autonomous containment is not sustainable.

Organizations should continue investing in governance, identity, least privilege, data security, secure MLOps, guardrails, testing, evaluation, validation, verification, kill switches, rollback, and forensic readiness. At the same time, they cannot wait for every governance program to mature before addressing runtime risk.

Behavioral-based detection and autonomous containment provide an immediate layer of resilience. They allow organizations to detect exploitation and risky AI behavior they did not anticipate, contain it at machine speed, and preserve human control over broader remediation.

The future of AI security will not be defined by a single model making every decision. It will be defined by multiple specialized AI systems working collaboratively, with sufficient accuracy, transparency, and context to support trusted autonomous action.

Surgical, explainable autonomous containment is no longer a future capability. It is a requirement for scaling AI securely today.

Learn how to build a defense-in-depth strategy for securing AI at scale in our talk at Black Hat on August 5 at 3:15 PM.  

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About the author
Nicole Carignan
SVP, Security & AI Strategy, Field CISO
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