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May 13, 2021

How AI Protects Critical Infrastructure From Ransomware

Explore the role of AI in safeguarding critical infrastructure from ransomware, as revealed by Darktrace's latest insights.
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
David Masson
VP, Field CISO
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13
May 2021

Modern Threats to OT Environments

At the 2021 RSA cyber security conference, US Secretary of Homeland Security Alejandro Mayorkas made an era-defining statement regarding the cyber security landscape: “Let me be clear: ransomware now poses a national security threat.”

Last weekend, Mayorkas’ words rang true. A ransomware attack on the Colonial Pipeline – responsible for nearly half of the US East Coast’s diesel, gasoline, and jet fuel – resulted in the shutdown of a critical fuel network supplying a number of Eastern states.

The fallout from the attack demonstrated how widespread and damaging the consequences of ransomware can be. Against critical infrastructure and utilities, cyber-attacks have the potential to disrupt supplies, harm the environment, and even threaten human lives.

Though full details remain to be confirmed, the attack is reported to have been conducted by an affiliate of the cyber-criminal group called DarkSide, and likely leveraged common remote desktop tools. Remote access has been enabled as an exploitable vulnerability within critical infrastructure by the shift to remote work that many organizations made last year, including those with Industrial Control Systems (ICS) and Operational Technology (OT).

The rise of industrial ransomware

Ransomware against industrial environments is on the rise, with a reported 500% increase since 2018. Oftentimes, these threats leverage the convergence of IT and OT systems, first targeting IT before pivoting to OT. This was seen with the EKANS ransomware that included ICS processes in its ‘kill list’, as well as the Cring ransomware that compromised ICS after first exploiting a vulnerability in a virtual private network (VPN).

It remains to be seen whether the initial attack vector in the Colonial Pipeline compromise exploited a technical vulnerability, compromised credentials, or a targeted spear phishing campaign. It has been reported that the attack first impacted IT systems, and that Colonial then shut down OT operations as a safety precaution. Colonial confirms that the ransomware “temporarily halted all pipeline operations and affected some of our IT systems,” showing that, ultimately, both OT and IT were affected. This is a great example of how many OT systems depend on IT, such that an IT cyber-attack has the ability to take down OT and ICS processes.

In addition to locking down systems, the threat actors also stole 100GB of sensitive data from Colonial. This kind of double extortion attack — in which data is exfiltrated before files are encrypted — has unfortunately become the norm rather than the exception, with over 70% of ransomware attacks involving exfiltration. Some ransomware gangs have even announced that they are dropping encryption altogether in favor of data theft and extortion methods.

Earlier this year, Darktrace defended against a double extortion ransomware attack waged against a critical infrastructure organization, which also leveraged common remote access tools. This blog will outline the threat find in depth, showing how Darktrace’s self-learning AI responded autonomously to an attack strikingly similar to the Colonial Pipeline incident.

Darktrace threat find

Ransomware against electric utilities equipment supplier

In an attack against a North American equipment supplier for electrical utilities earlier this year, Darktrace/OT demonstrated its ability to protect critical infrastructure against double extortion ransomware that targeted organizations with ICS and OT.

The ransomware attack initially targeted IT systems, and, thanks to self-learning Cyber AI, was stopped before it could spill over into OT and disrupt operations.

The attacker first compromised an internal server in order to exfiltrate data and deploy ransomware over the course of 12 hours. The short amount of time between initial compromise and deployment is unusual, as ransomware threat actors often wait several days to spread stealthily as far across the cyber ecosystem as possible before striking.

Figure 1: A timeline of the attack

How did the attack bypass the rest of the security stack?

The attacker leveraged ‘Living off the Land’ techniques to blend into the business’ normal ‘patterns of life’, using a compromised admin credential and a remote management tool approved by the organization, in its attempts to remain undetected.

Darktrace commonly sees the abuse of legitimate remote management software in attackers’ arsenal of techniques, tactics, and procedures (TTPs). Remote access is also becoming an increasingly common vector of attack in ICS attacks in particular. For example, in the cyber-incident at the Florida water treatment facility last February, attackers exploited a remote management tool in attempts to manipulate the treatment process.

The specific strain of ransomware deployed by this attacker also successfully evaded detection by anti-virus by using a unique file extension when encrypting files. These forms of ‘signatureless’ ransomware easily slip past legacy approaches to security that rely on rules, signatures, threat feeds, and lists of documented Common Vulnerabilities and Exposures (CVEs), as these are methods that can only detect previously documented threats.

The only way to detect never-before-seen threats like signatureless ransomware is for a technology to find anomalous behavior, rather than rely on lists of ‘known bads’. This can be achieved with self-learning technology, which spots even the most subtle deviations from the normal ‘patterns of life’ for all devices, users, and all the connections between them.

Darktrace insights

Initial compromise and establishing foothold

Despite the abuse of a legitimate tool and the absence of known signatures, Darktrace/OT was able to use a holistic understanding of normal activity to detect the malicious activity at multiple points in the attack lifecycle.

The first clear sign of an emerging threat that was alerted by Darktrace was the unusual use of a privileged credential. The device also served an unusual remote desktop protocol (RDP) connection from a Veeam server shortly before the incident, indicating that the attacker may have moved laterally from elsewhere in the network.

Three minutes later, the device initiated a remote management session which lasted 21 hours. This allowed the attacker to move throughout the broader cyber ecosystem while remaining undetected by traditional defences. Darktrace, however, was able to detect unusual remote management usage as another early warning indicative of an attack.

Double threat part one: Data exfiltration

One hour after the initial compromise, Darktrace detected unusual volumes of data being sent to a 100% rare cloud storage solution, pCloud. The outbound data was encrypted using SSL, but Darktrace created multiple alerts relating to large internal downloads and external uploads that were a significant deviation from the device’s normal ‘pattern of life’.

The device continued to exfiltrate data for nine hours. Analysis of the files downloaded by the device, which were transferred using the unencrypted SMB protocol, suggests that they were sensitive in nature. Fortunately, Darktrace was able to pinpoint the specific files that were exfiltrated so that the customer could immediately evaluate the potential implications of the compromise.

Double threat part two: File encryption

A short time later, at 01:49 local time, the compromised device began encrypting files in a SharePoint back-up share drive. Over the next three and a half hours, the device encrypted over 13,000 files on at least 20 SMB shares. In total, Darktrace produced 23 alerts for the device in question, which amounted to 48% of all the alerts produced in the corresponding 24-hour period.

Darktrace’s Cyber AI Analyst then automatically launched an investigation, identifying the internal data transfers and the file encryption over SMB. From this, it was able to present incident reports that connected the dots among these disparate anomalies, piecing them together into a coherent security narrative. This put the security team in a position to immediately take remediating action.

If the customer had been using Darktrace’s autonomous response technology, there is no doubt the activity would have been halted before significant volumes of data could have been exfiltrated or files encrypted. Fortunately, after seeing both the alerts and Cyber AI Analyst reports, the customer was able to use Darktrace’s ‘Ask the Expert’ (ATE) service for incident response to mitigate the impact of the attack and assist with disaster recovery.

Figure 2: AI Analyst Incident reporting an unusual reprogram command using the MODBUS protocol. The incident includes a plain English summary, relevant technical information, and the investigation process used by the AI.  

Detecting the threat before it could disrupt critical infrastructure

The targeted supplier was overseeing OT and had close ties to critical infrastructure. By facilitating the early-stage response, Darktrace prevented the ransomware from spreading further onto the factory floor. Crucially, Darktrace also minimized operational disruption, helping to avoid the domino effect which the attack could have had, affecting not only the supplier itself, but also the electric utilities that this supplier supports.

As both the recent Colonial Pipeline incident and the above threat find reveal, ransomware is a pressing concern for organizations overseeing industrial operations across all forms of critical infrastructure, from pipelines to the power grid and its suppliers. With self-learning AI, these attack vectors can be dealt with before the damage is done through real-time threat detection, autonomous investigations, and — if activated — targeted machine-speed response.

Looking forward: Using Self-Learning AI to protect critical infrastructure across the board

In late April, the Biden administration announced an ambitious effort to “safeguard US critical infrastructure from persistent and sophisticated threats.” The Department of Energy’s (DOE) 100-day plan specifically seeks technologies “that will provide cyber visibility, detection, and response capabilities for industrial control systems of electric utilities.”

The Biden administration’s cyber sprint clearly calls for a technology that protects critical energy infrastructure, rather than merely best practice measures and regulations. As seen in the above threat find, Darktrace AI is a powerful technology that leverages unsupervised machine learning to autonomously safeguard critical infrastructure and its suppliers with machine speed and precision.

Darktrace enhances detection, mitigation, and forensic capabilities to detect  sophisticated and novel attacks, along with insider threats and pre-existing infections, using Self-Learning Cyber AI, without rules, signatures, or lists of CVEs. Incident investigations provided in real time by Cyber AI Analyst jumpstart remediation with actionable insights, containing emerging attacks at their early stages, before they escalate into crisis.

Enable near real-time situational awareness and response capabilities

Darktrace immediately understands, identifies, and investigates all anomalous activity in ICS/OT networks, whether human or machine driven. Additionally, Darktrace actions targeted response where appropriate to neutralize threats, either actively or in human confirmation mode. Because Self-learning AI adapts alongside evolutions in the ecosystem, organizations benefit from real-time awareness with no tuning or human input necessary

Deploy technologies to increase visibility of threats in ICS and OT systems

Darktrace contextualizes security events, adapts to novel techniques, and translates findings into a security narrative that can be actioned by humans in minutes. Delivering a unified view across IT and OT systems.

Darktrace detects, investigates, and responds to threats at higher Purdue levels and in IT systems before they ‘spill over’ into OT. ‘Plug and play’ deployment seamlessly integrates with technological architecture, presenting 3D network topology with granular visibility into all users, devices, and subnets.

Darktrace's asset identification continuously catalogues all ICS/OT devices and identifies and investigates all threatening activity indicative of emerging attacks – be it ICS ransomware, APTs, zero-day exploits, insider threats, pre-existing infections, DDoS, crypto-mining, misconfigurations, or never-before-seen attacks.

Thanks to Darktrace analyst Oakley Cox for his insights on the above threat find.

Darktrace model detections:

  • Initial compromise:
  • User / New Admin Credential on Client
  • Data exfiltration:
  • Anomalous Connection / Uncommon 1 GiB Outbound
  • Anomalous Connection / Low and Slow Exfiltration
  • Device / Anomalous SMB Followed by Multiple Model Breaches
  • Anomalous Connection / Download and Upload
  • File encryption:
  • Compromise / Ransomware / Suspicious SMB Activity
  • Anomalous Connection / SMB Enumeration
  • Device / Anomalous RDP Followed by Multiple Model Breaches
  • Anomalous File / Internal / Additional Extension Appended to SMB File
  • Anomalous Connection / Sustained MIME Type Conversion
  • Anomalous Connection / Suspicious Read Write Ratio
  • Device / Multiple Lateral Movement Model Breaches

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
David Masson
VP, Field CISO

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August 5, 2026

Testing a Prompt injection Attack Against an Enterprise AI Agent

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Key takeaways

  • Darktrace successfully detected and quarantined a prompt injection email before it could be processed by an enterprise AI agent.  
  • Prompt injection attacks increasingly rely on natural language rather than traditional malware, making behavioral analysis an important complement to signature-based detection.  
  • Organizations deploying AI agents should combine model guardrails with behavioral monitoring to reduce the risk of malicious instructions reaching enterprise systems.

How behavioral detection helps stop prompt injection attacks

A Darktrace customer running a Gemini AI agent in Google Cloud asked us two simple questions:

“If my agent can read inbound emails and access internal data, what stops an attacker from hiding malicious instructions in the message? Couldn’t the agent be tricked into deleting or exfiltrating sensitive data?”

The scenario centers on an indirect prompt injection attack, where malicious instructions are hidden inside content that an AI model later interprets as trusted input. The same weakness was exposed by  EchoLeak (CVE-2025-32711), a zero-click Microsoft 365 Copilot vulnerability enabled data exfiltration from a single well-crafted email..

This blog follows the Darktrace team’s investigation of the customer’s hypothesis and examines how the attack interacted with their existing security stack. The results highlight which defenses held, where gaps emerged, and how behavioral detection mattered more than guardrails. This investigation also demonstrates why behavioral detection is becoming increasingly important for AI security, as prompt injections often contain no traditional indicators of compromise.  

How do prompt injection attacks work?

Prompt injection works by carefully crafting the content and structure of the prompt to alter the LLM’s behavior or output in unintended ways. This can cause models to violate guardrails, generate harmful content or enable unauthorised access.

Prompt injection attack example

The well-known example, EchoLeak (CVE-2025-32711), was a zero-click vulnerability in Microsoft 365 Copilot that relied on a carefully crafted email containing hidden instructions that the AI system interpreted as commands rather than content, creating a pathway for unauthorized access to sensitive information without any user interaction.

While Darktrace / SECURE AI is designed to prevent agents from producing unintended outcomes, we wanted to see if we could catch and prevent this threat type earlier in the attack life-cycle, at the email security layer.

How we tested prompt injection attacks on an enterprise agent

Summary:

  1. Claude generated a prompt injection payload.  
  2. Hidden instructions were embedded in an email.  
  3. The email passed traditional validation checks.  
  4. Darktrace analyzed the language and sender behavior.  
  5. The email was quarantined before the AI agent could process it.

To test Darktrace / EMAIL against this attack class, we opened Claude, gave it the customer's context and problem statement (Gemini agent with inbox access, internal tool calls), told it we were validating Darktrace / EMAIL's detection of prompt injections, and asked for a test payload. See below:

Figure 1
Figure 2

Despite the guardrails supposedly built into the model, Claude surprisingly gave us the entire exploit in plaintext (albeit very basic), illegible to a human as the text was sent in white text (see Figure 1) but framed as an authoritative override for anything downstream reading the mail programmatically (i.e. the Gemini agent).

How Darktrace detected a prompt injection attack

We then sent the Claude-crafted email from a freemail address to the target recipient’s inbox. Despite the email containing no malicious payload, the freemail address having no malicious reputation, and the validation checks all passing, Darktrace  /EMAIL flagged the email as a 93/100 anomaly and moved it to junk, out of scope for the AI agent.

Figure 3: The test email sent with the hidden prompt injection
Figure 4: The email analysis in Darktrace / EMAIL 
Figure 5: Darktrace / EMAIL detection of malicious activity

The interesting part is what triggered the detection (see Figure 5)

  • Possible machine prompt content: text in the body detected as instructions written for a machine to execute, not for a human to read
  • Possible machine prompt content + basic suspicious correspondence: the same content, correlated with sender-side anomalies: freemail domain (yahoo[.]com), unknown correspondent, no prior mail history with the recipient, and suspicious references to payment information

Neither of those is a signature match. Nothing in the email was on a blacklist. There was no malware, no link and no attachment. Darktrace analyzed the context in which the email was delivered and flagged it as likely risky.  The anomalous language features and the context of the sender relative to the recipient's normal behavior, combined with the unusual hidden text (prompt) were enough for Darktrace / EMAIL to act on the risk.

Result: Darktrace / EMAIL autonomously junked the email, out of scope for any AI agent parsing the inbox.

Why behavioral security makes a difference detecting prompt injection attacks

Cyberattacks don't look like traditional exploits anymore. They now operate in natural language, not strictly code.

That breaks the traditional stack. AV, firewalls, static scanning and signature-based SEGs all assume a payload to inspect.  

A prompt injection has no payload. It's just an instruction, written in natural language, dressed up as anything the attacker wants: an invoice, an HR request, a calendar invite, some simple PowerPoint slides.

EchoLeak proved that hidden instructions can sit inside an email invisible to the user but fully readable by the LLM, and the LLM will follow them blindly.  

This test and GTG-1002 proved that the LLM itself can be socially engineered. Tell it you're an authorized tester and it will hand you the attack.

Rules and static classifiers can catch the obvious cases. But natural language has infinite variants, and the attack surface is the model's innate functionality to comply.  

The deeper problem here is intent: an LLM can't reliably tell whether an instruction in its context came from its developer, its user, or an attacker who slipped it into an email. To the LLM, everything reads as language and looks like a legitimate ask. This is why behavioural detection wins, as you become aware of intent when you look at the context of an interaction. Does this sender normally send this kind of message to this recipient? Does this prompt fit the user's normal pattern? Is this agent behaving the way this agent normally behaves?  

Intent can't be read off a single email, it emerges from behavioral context. Which is how Darktrace enables threat detection, through behavioral understanding.

Why enterprise AI security requires more than guardrails

Claude didn't roll over immediately… the first section of the response was a (slight) pushback, but then it wrote the payload anyway without having to ask twice.

Here the framing of the prompt did all the work. The “testing security capabilities” angle moved the model from refusal to unquestioned compliance to the user prompt.

This isn't the first time this has happened, of course. Anthropic disclosed in November 2025 that a Chinese state-sponsored group they tracked as GTG-1002 ran the first documented AI-orchestrated espionage campaign against ~30 targets by posing as employees of a legitimate cybersecurity firm doing authorised penetration testing.

The takeaway isn't that AI guardrails are ineffective. They raise the cost of low-effort attacks and remain an important first layer of defense. However, for most organizations today, they’re the only line of defense when deploying AI agents. If a prompt injection bypasses those controls, organizations still need a way to detect and stop malicious behavior elsewhere in the attack chain.

Attackers will continue to have working prompt injections easily and quickly. The question is what stops one when it lands in an inbox your agent is reading.

That's where behavioral detection comes in.

How Darktrace detects prompt injection attacks in emails

Two things Darktrace does that a model-level guardrail or static rules and signatures can't:

Natural language analysis at the email or prompt layer. The email is assessed on its own merits: is this content shaped like instructions for a machine, regardless of what the receiving agent decides to do about it?

Behavioral context around the language. An AI agent behaves like an extremely agreeable human, and it will go above and beyond to comply with the user’s request. That's exactly why you must consider the business context, such sender behaviour, mailing history, and organisational norms, as these matter even more when the recipient is an AI.

Darktrace has been perfecting behavioral anomaly detection for over a decade; the same self-learning approach that catches BEC and account takeover applies directly to prompt injection delivery. Our multi-layered AI stack extracts content from the message, builds behavioural understanding through social graphing and Pattern of Life analysis, and then combines natural language, topic, inducement, sender relationship and anomaly signals before deciding what action to take.  

This matters for prompt injection because the threat is not the plain language itself, but the intent behind the language that can cause an AI agent to respond in unexpected ways.

How to secure enterprise AI operations from prompt injection attacks

Email was the entry point in this case, but it is only one of many possible vectors.  

Anywhere an agent can retrieve information, an attacker can potentially introduce a prompt injection.

Emails, documents, SharePoint sites, web pages, knowledge bases, chat platforms, and third-party integrations all provide opportunities to influence an agent's behavior. Wherever an agent finds its orders, a prompt injection opportunity exists.

This is why securing AI requires more than blocking malicious inputs. Organizations also need visibility into how agents behave after consuming information from across their environment. If an agent begins accessing unexpected data, taking unusual actions, or operating outside its normal patterns, those behaviors may provide the strongest signal that something has gone wrong.

Effective AI security requires defense in depth: reducing the likelihood of malicious instructions reaching the agent while maintaining the ability to detect and investigate suspicious behavior if they do.

The challenge isn't protecting a single entry point. It's recognizing that, in an AI-powered environment, every source of information is also a potential source of influence.

Are you deploying autonomous agents across your enterprise and want to see this tested in your environment? Let's talk.

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Carlo Loregian
Solutions Engineer

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August 4, 2026

Extending AI Security Visibility with Darktrace and Microsoft Agent 365

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AI agents are rapidly becoming embedded in everyday business operations, helping employees automate workflows, access information, and accelerate decision-making. As organizations embrace agentic AI, security teams face a growing challenge: understanding how AI is being used, what agents can access, and where risk may emerge.

As agents take on more business-critical work, security teams often need to move across multiple portals to understand risks spanning identity, data, and threat activity. This fragmented view can make it difficult to assess an agent's overall risk posture and determine where attention is needed. Organizations need a way to bring these signals together without disrupting existing security investments or workflows.

Today, Darktrace is announcing an integration between Darktrace / SECURE AI and Microsoft Agent 365 that brings Darktrace's Adaptive AI-driven risk signals directly into the Microsoft 365 Admin Center. By extending the visibility and risk understanding provided by Darktrace / SECURE AI into the Microsoft ecosystem, organizations can gain a more unified understanding of AI agent risk across their environments.

As one of the first security companies to partner with Microsoft to contribute third-party risk signals to the Agent Registry, Darktrace is helping shape how organizations understand and manage AI agent risk.

Extending visibility into the Microsoft Agent 365 experience

Microsoft Agent 365 provides administrators with a centralized registry of AI agents operating within their environment. As organizations expand their use of AI agents, this centralized visibility becomes increasingly important for governance and oversight.

This new integration extends that visibility by allowing Darktrace-generated risk signals to be surfaced directly within the Microsoft Agent 365 experience. By combining Microsoft's agent management and security capabilities with Darktrace's AI-powered risk analysis, organizations gain greater awareness of potential security concerns associated with AI agents operating across their environments.

By integrating Darktrace telemetry into Agent 365, customers can:  

  • Surface Darktrace-detected risks and signals alongside Microsoft-native signals in a single interface
  • Identify potentially compromised or anomalous AI agents more quickly
  • Gain unified understanding of context and agent behavior  

This approach reinforces a single control plane for AI security while allowing organizations to continue leveraging existing investments across both platforms.  

Why unified visibility of AI agent risk signals matters

As AI adoption accelerates across Microsoft environments, organizations must manage new forms of behavior, access patterns, and risk. Security teams need more than inventories and permissions. They need visibility into how AI systems operate and how risk evolves over time.  

This integration addresses a critical gap: how to bring behavioral AI security insights into the same control plane as identity, access, and agent management.  

With Darktrace and Microsoft Agent 365 together, organizations benefit from:  

  • Unified visibility: A single pane of glass for understanding AI agent risk signals across Microsoft and Darktrace signals  
  • Faster detection of abnormal agent behavior: Darktrace's Adaptive AI highlights deviations that may not be captured by static controls  
  • Operational efficiency: Security teams can triage and prioritize risk signals without switching between systems
  • Stronger trust in AI deployments: Clear attribution, context, and investigation pathways improve confidence in AI agent usage

Extending Microsoft's AI security model, not replacing it

Securing AI requires a layered approach that combines governance, visibility, threat detection, and risk management. This integration is designed to complement Microsoft's security capabilities, not duplicate them.  

Through Darktrace / SECURE AI, Darktrace contributes:  

  • Identification of risk via advanced prompt analysis  
  • Behavioral anomaly detection across AI agents  
  • Cross-environment threat correlation  
  • Autonomous insight into emerging or unknown risks  

Microsoft provides:  

  • Centralized agent management
  • Identity and access governance
  • Native detection of risk signals and enforcement capabilities

Together, these capabilities create a more complete, layered approach to securing AI-driven enterprises. Organizations gain the governance and policy controls needed to manage AI adoption while benefiting from continuous visibility into how AI is used across the business.

Building the future of secure AI

As AI agents become more deeply embedded in business processes, organizations need more than inventories and static controls. They need to understand how AI is being used, how agents behave, and where risk is emerging across the enterprise.

Darktrace / SECURE AI delivers that understanding through continuous visibility into AI activity, helping security teams assess intent, identify behavioral drift, and uncover emerging risk across both human and agent-driven workflows. Powered by Adaptive AI, it provides the context needed to secure AI as it evolves.  

The integration with Microsoft Agent 365 extends those insights into the workflows organizations already use. Agent 365 provides a unified control plane for governing and securing AI agents, while Darktrace contributes complementary behavioral risk signals that can be surfaced within the Agent 365 experience. Together, they give customers broader context on agent activity and risk while preserving the value of their existing Microsoft and Darktrace investments.

As enterprises move from AI experimentation to AI-powered execution, Microsoft and Darktrace help bring together governance, compliance, behavioral understanding, and oversight in a unified approach to AI security. For organizations adopting Microsoft 365 E7, Darktrace / SECURE AI further strengthens that foundation by providing continuous visibility into AI activity, agent behavior, and emerging risk as AI adoption scales.

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