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June 3, 2019

How Cyberseer Detected Advanced Red Team Activity

This guest-authored blog post examines how Cyberseer detected highly advanced red team activities with Darktrace’s Enterprise Immune System.
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
Michael Green
Lead Security Analyst at Cyberseer (Guest Contributor)
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03
Jun 2019

The following guest-authored blog post examines how Cyberseer detected highly advanced red team activities with Darktrace’s Enterprise Immune System.

At Cyberseer, a managed security provider, our analysts know that thwarting sophisticated cyber-criminals requires being prepared for any eventuality. A red team attack today could easily be replicated by far less benign actors tomorrow, which is why we treat these exercises with the same gravity we would a genuine threat, employing the world’s most advanced AI cyber defenses like Darktrace to leave the bad guys without anywhere to hide.

Recently, one of our customers was involved in a red team assessment, partly as a means to see how their security team would react and contain the attack, and partly to determine the visibility of the different attack techniques across their security stack. During the engagement, the red team leveraged a number of stealthy “Living off the Land” (LotL) techniques. LotL refers to the malicious use of legitimate tools present on a system — such as PowerShell scripting, WMI, or PsExec — in order to execute attacks. It should be noted that these techniques are not just limited to red teamers: threat-actors are making use of such tools on compromised systems, a notable example being the 2017 Petya/NotPetya attack.

Here’s an example of how Cyberseer’s analysts used Darktrace to detect the red team, without prior knowledge of their techniques, in real time:

Invoke — Bloodhound

Created by professional penetration tester Andy Robbins, Bloodhound is an open source tool that uses graph theory to understand the relationships in an Active Directory (AD) environment. It can be harnessed to quickly gain deep insights into AD by enumerating all the computers for which a given user has admin rights, in addition to ascertaining group membership information. In the right hands, security teams can use Bloodhound to identify and then limit attack vectors. In the wrong hands, attackers can easily exploit these same pathways if left unaddressed.

To collect data, Bloodhound is complemented by a data ingestor called Sharphound, which comes either as a PowerShell script or an executable. Sharphound makes use of native Windows APIs to query and retrieve information from target hosts. For example, to enumerate Local Admin users, it calls ‘NetLocalGroupGetMember’ API to interact with the Security Account Manager (SAM) database file on the remote host.

These tools typically produce a number of artifacts that we would expect to see from the host device within network traffic:

  • Increase in connections to LDAP (389) and SMB (445) ports
  • Increase in connections to IPC$ shares
  • Increase in Distributed Computing Environment / Remote Procedure Calls (DCE_RPC) Connections to the following named pipes:
  • \PIPE\wkssvc - Query logged-in users
  • \PIPE\srvsvc - Query system information
  • \PIPE\svcctl - Query services with stored credentials
  • \PIPE\atsvc - Query scheduled tasks
  • \PIPE\samr - Enumerate domain and user information
  • \PIPE\lsass - Extract credential information

Associating this back to the red team engagement, upon execution of the Bloodhound tool the attacking device began reaching out to a large number of internal devices, causing a spike in internal connections:

Figure 1: Darktrace visualizing the increase in internal connections, with each dot representing a unique model breach triggered by Bloodhound activity.

In fact, the large volume of anomalous connections triggered a number of Darktrace’s behavioral models, including:

  • Anomalous Connection / SMB Enumeration
  • Anomalous Connection / New Service Control
  • Device / Network Scan
  • Device / Expanded Network Scan
  • Unusual Activity / Unusual Activity from Multiple Metrics
  • Unusual Activity / Sustained Suspicious Activity
  • Unusual Activity / Sustained Unusual Activity

Drilling deeper into these connections, it was possible to identify the named \PIPE\ connections that were detailed above:

Figure 2: Reviewing the raw connection logs within Darktrace’s Advanced Search.

Looking from top to bottom, we see scanning of devices on ports 139 and 445, access to remote IPC$ shares, SMB read / writes of the srvsvc, and samr pipes and lsass binds. Although these protocols have legitimate applications within a typical network, a device initiating so many of them within a short time frame warrants further investigation.

Darktrace AI not only shined a light on these activities, it automatically determined that they were potentially threatening despite being benign under most circumstances. Rooted in an ever-evolving understanding of our customer’s normal ‘pattern of life’, Darktrace correlated numerous weak indicators of anomalous behavior to flag the activity as a significant risk within seconds.

Invoke — PasswordSpray

“Password spraying” is an attack that targets a large number of accounts with a few commonly used passwords. In this case, for instance, the red team attempted to brute-force access to a file share. Although this tactic may seem rudimentary, a recent study by the NCSC found that 75% of organizations had accounts with passwords that featured in the top 1,000 passwords, while 87% had accounts with passwords that featured in the top 10,000.

Similar to the previous Bloodhound attack, the password spraying attack began with an increase in SMB connections on port 445. Darktrace alerted to even this relatively small number of connections, since it was anomalous for our customer’s unique network:

Figure 3: Volume of SMB session failures made to file shares from the attacker’s device.

Each of these connections was making use of a user credential and random password. From the logs below it is possible to see all of the SMB session failures:

Figure 4: A device event log showing repeated SMB session failures for each of the unsuccessful authentication attempts.

Even with only 50 total attempts seen, Darktrace quickly alerted upon both SMB enumeration and brute-force behaviors.

Both of these scenarios highlight the benefits of an AI-powered approach. Rather than focusing on hash or string matches for such tools, Darktrace is able to quickly identify anomalous patterns of behavior linked with their usage. This nuance is particularly critical in this case, given that all of these activities are not malicious in many situations. By differentiating between subtle threats and harmless traffic, Darktrace helps us defeat red teams and real criminals alike.

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
Michael Green
Lead Security Analyst at Cyberseer (Guest Contributor)

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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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Carlos Gray
Senior Product Marketing Manager, Email

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July 23, 2026

When AI Agents Go Off Script: What the OpenAI and Hugging Face Incident Means for Defenders

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The recent security incident disclosed jointly by OpenAI and Hugging Face is quickly becoming one of the most discussed AI security stories of the year; it's one that has generated great discussion amongst our researchers and technical teams here at Darktrace.

During an internal evaluation of advanced OpenAI models, an autonomous agent reportedly escaped its intended testing boundaries, obtained internet access, and compromised Hugging Face infrastructure while attempting to evaluate and benchmark the model's cyber capabilities. OpenAI has described it as an unprecedented cyber incident and is collaborating with Hugging Face to investigate and share its findings publicly to help defenders understand the implications and improve AI safety across the community.

What this means for organizations deploying AI agents

The most important takeaway for security leaders is not that the AI model is capable of complex and effective chained attacks. It's what this tells us about the guardrails and protections that need to be put in place to ensure these increasingly capable models are safely used within our businesses.

According to OpenAI's investigation, the models were not acting with malicious intent. They were attempting to achieve a legitimate assigned objective. In pursuing that objective, they identified a path that involved obtaining information from a third party's environment and followed it to completion. From the model's perspective, that appears to have been an effective solution to the problem it was given.

Many organizations still hold the assumption that giving an AI agent a legitimate goal will naturally result in legitimate behavior. Increasingly, that is not something defenders can safely assume.

A human who encounters a "permission denied" message generally understands the technical restriction as well as the social meaning behind it. An agent may interpret that message only as evidence that one method to achieve its objective has failed. What makes this incident notable is the agent’s ability to keep pursuing the objective, revise its plan, and combine many individually useful actions into an outcome its designers did not intend.

This is not an isolated challenge. Recent research from the UK's AI Security Institute found that frontier models often attempt to "cheat" evaluations by finding unintended shortcuts to success. More interestingly, that behavior is not always reflected in chain-of-thought outputs and is not always admitted when models are questioned about their actions. One lesson for defenders is that understanding what an AI system says it is doing is not always the same as understanding its behavior and what it is actually doing.

Why behavioral security is an essential security foundation

That's the principle behind Darktrace / SECURE AI and our broader approach to behavioral security. Understanding intent or putting in place static guardrails is not enough; security teams need visibility into how agents behave over time, what resources they interact with, how their behavior changes, and whether they begin pursuing objectives in unexpected ways. Research released by NIST earlier this summer reinforced that rules alone are not sufficient to defend against AI threats, with one conclusion being that "there will always be a way to prompt an AI system to disregard its rules - it's just a matter of finding it."

Another interesting lesson is that nothing described in OpenAI's preliminary findings appears fundamentally impossible for a skilled human attacker. But it does highlight the accessibility and scale that could be unlocked for attackers as increasingly capable models become more widely available. Resource constraints that attackers deal with will decrease as frontier models can help execute elements of those attack workflows autonomously, persist through failure, and iterate towards an objective. Capabilities that were once limited to skilled attackers can increasingly be supplemented with these systems, lowering the barrier to entry to conduct complex cyber operations.

It is incredibly positive to see OpenAI and Hugging Face investigating this incident collaboratively and sharing their findings publicly. Transparency and collaboration around incidents like these helps the entire security community better understand how rapidly AI capabilities are evolving and where we need to improve safeguards. It also reinforces why Darktrace is excited to be partnering with OpenAI through the Daybreak Cyber Partner Program: to explore how advanced AI can be used safely and responsibly in support of defenders while developing the visibility, governance, and security controls needed for increasingly autonomous systems.

This incident is an important reminder that capable AI systems will not always behave in the ways we expect. As organizations deploy AI agents across critical workflows, understanding behavior is an even more important foundation for effective security.

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About the author
Dr. Tim Bazalgette
Chief AI Officer, Darktrace
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