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April 13, 2022

Efficient Incident Reporting: Darktrace AI Analyst

Discover how Darktrace's Cyber AI Analyst accelerates incident reporting to the US federal government, enhancing cybersecurity response times.
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
Justin Fier
SVP, Red Team Operations
Written by
Sally Kenyon Grant
VP, Darktrace Federal
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13
Apr 2022

On March 15, 2022, President Biden signed the Cyber Incident Reporting for Critical Infrastructure Act into law, included as part of the Congressional Omnibus Appropriations bill. The law requires critical infrastructure owners and operators to quickly notify the Cyber and Infrastructure Security Agency (CISA) of ransomware payments and significant cyber-attacks.

The Cyber Incident Reporting for Critical Infrastructure Act creates two new reporting requirements:

  1. an obligation to report certain cyber incidents to DHS CISA within 72 hours
  2. an obligation to report ransomware payments within 24 hours

Supporting the new law, Darktrace AI accelerates the cyber incident reporting process. Specifically, Darktrace’s Cyber AI Analyst understands the connections among disparate security incidents with supervised machine learning and autonomously writes incident reports in human-readable language using natural language processing (NLP). These Darktrace incident reports allow human analysts to send reports to CISA quickly and efficiently.

In the below real-world attack case study, we demonstrate how Cyber AI Analyst facilitates seamless reporting for critical infrastructure organizations that fall victim to ransomware and malicious data exfiltration. The AI technology, trained on human analyst behavior, replicates investigations at machine speed and scale, surfacing relevant details in minutes and allowing security teams to understand what happened precisely and share this information with the relevant authorities.

The below threat investigation details a significant threat find on a step by step level in technical detail to demonstrate the power and speed of Cyber AI Analyst.

Cyber AI Analyst’s incident report

When ransomware struck this organization, Cyber AI Analyst was invaluable, autonomously investigating the full scope of the incident and generating a natural language summary that clearly showed the progression of the attack.

Figure 1: Cyber AI Analyst reveals the full scope of the attack

In the aftermath of this attack, Darktrace’s technology also offered analyst assistance in mapping out the timeline of the attack and identifying what files were compromised, helping the security team identify anomalous activity related to the ransomware attack.

Figure 2: Cyber AI Analyst showing the stages of the attack chain undergone by the compromised device

With Darktrace AI’s insights, the team easily identified the timeline of the attack, affected devices, credentials used, file shares accessed, files exfiltrated, and malicious endpoints contacted, enabling the customer to disclose the scale of the attack and notify necessary parties.

This example demonstrates how Cyber AI Analyst empowers critical infrastructure owners and operators to swiftly report major cyber-attacks to the federal government. Considering that 72 hours is the reporting period is for significant incidents — and 24 hours for ransomware payments — Cyber AI Analyst is no longer a nice-to-have but a must-have for critical infrastructure.

Attack breakdown: Ransomware and data exfiltration

Cyber AI Analyst delivered the most critical information in an easy-to-read report — with no human touch involved — as shown in the incident report above. We will now break down the attack further to demonstrate how Darktrace’s Self-Learning AI understood the unusual activity throughout the attack lifecycle.

In this double extortion ransomware, attackers exfiltrated data over 22 days. The detections made by Darktrace’s Self-Learning AI, and the parallel investigation by Cyber AI Analyst, were used to map the attack chain and identify how and what data had been exfiltrated and encrypted.

The attack consisted of three general groups of events:

  • Unencrypted FTP (File Transfer Protocol) data exfiltration to rare malicious external endpoint in Bulgaria (May 9 07:23:46 UTC – May 21 03:06:46 UTC)
  • Ransomware encryption of files in network file shares (May 25 01:00:27 UTC – May 30 07:09:53 UTC)
  • Encrypted SSH (Secure Shell) data exfiltration to rare malicious external endpoint (May 29 16:43:37 UTC – May 30 13:23:59 UTC)
Figure 3: Timeline of the attack alongside Darktrace model breaches

First, uploads of internal data to a rare external endpoint in Bulgaria were observed within the networks. The exfiltration was preceded by SMB reads of internal file shares before approximately 450GB of data was exfiltrated via FTP.

Darktrace’s AI identified this threatening activity on its own, and the organization was quickly able to pinpoint what data had been exfiltrated, including files camouflaged by markings such as ‘Talent Acquisition’ and ‘Engineering and Construction,’ and legal and financial documents — suggesting that these were documents of an extremely sensitive nature.

Figure 4: Screenshots showing two model breaches relating to external uploads over FTP
Figure 5: Screenshot showing SMB reads from a file share before FTP upload

Model breaches:

  • Anomalous Connection / Unusual Incoming Data Volume
  • Anomalous File / Internal / Additional Extension Appended to SMB File
  • Compromise / Ransomware / Suspicious SMB Activity
  • Compromise / Ransomware / SMB Reads then Writes with Additional Extensions
  • Unusual Activity / Anomalous SMB Move & Write
  • Unusual Activity / High Volume Server Data Transfer
  • Unusual Activity / Sustained Anomalous SMB Activity
  • Device / SMB Lateral Movement

Four days following this observed activity, Darktrace’s AI detected the deployment of ransomware when multiple compromised devices began making anomalous SMB connections to file shares that they do not typically access, reading and writing similar volumes to the SMB file shares, as well as writing additional extensions to files over SMB. The file extension comprised a random string of letters and was likely to be unique to this target.

Using Darktrace, the customer obtained a full list of files that had been encrypted. The list included apparent financial records in an ‘Accounts’ file share.

Figure 6: Model breach showing additional extension written to file during ransomware encryption

Model breaches:

  • Anomalous Connection / Unusual Incoming Data Volume
  • Anomalous File / Internal / Additional Extension Appended to SMB File
  • Compromise / Ransomware / Suspicious SMB Activity
  • Compromise / Ransomware / SMB Reads then Writes with Additional Extensions
  • Unusual Activity / Anomalous SMB Move & Write
  • Unusual Activity / High Volume Server Data Transfer
  • Unusual Activity / Sustained Anomalous SMB Activity
  • Device / SMB Lateral Movement

Simultaneously, uploads of internal data to a rare external endpoint were observed within the network. The uploads were all performed using encrypted SSH/SFTP. In total, approximately 3.5GB of data was exfiltrated this way.

Despite the attacker using an encrypted channel to exfiltrate this data, Darktrace detected anomalous SMB file transfers prior to the external upload, indicating which files were exfiltrated. Here, Darktrace’s ability to go ‘back in time’ proved invaluable in helping analysts determine which files had been exfiltrated, although they were exfiltrated via an encrypted means.

Figure 7: Model breaches showing anomalous SMB activity before upload over SSH

Model breaches:

  • Anomalous Server Activity / Outgoing from Server
  • Compliance / SSH to Rare External Destination
  • Unusual Activity / Enhanced Unusual External Data Transfer
  • Device / Anomalous SMB Followed By Multiple Model Breaches
  • Device / Large Number of Model Breaches
  • Anomalous Connection / Uncommon 1 GiB Outbound
  • Anomalous Connection / Data Sent to Rare Domain
  • Anomalous Connection / Data Sent To New External Device

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

Existing administrative credentials were used to escalate privileges within the network and perform malicious activity.

Had Darktrace Antigena been active, it would have actioned a targeted, autonomous response to contain the activity in its early stages. Antigena would have enforced the ‘pattern of life’ on the devices involved in anomalous SMB activity — containing activity such as reading from file shares that are not normally connected, appending extensions to files and blocking outgoing connections to rare external endpoints.

However, in this case, Antigena was not set up to take action – it was configured in Human Confirmation mode. The incident was clearly alerted on by Darktrace, and appeared as a top priority item in the security team’s workflow. However, the security team was not monitoring Darktrace’s user interface, and in the absence of any action taken by other tools, the attack was allowed to progress, and the organization was obligated to disclose the details of the incident.

Streamlining the reporting process

In the modern threat landscape, leaning on AI to stop fast-moving and sophisticated attacks at machine speed and scale is critical. As this attack shows, the technology also helps organizations fulfill reporting requirements in the aftermath of an attack.

New legislation requires timely disclosure; with many traditional approaches to security, organizations do not have the capacity to surface the full details after an attack. On top of this, collating these details can take days or weeks. This is why Darktrace is no longer a nice-to-have but a must-have for critical infrastructure organizations, which are now required to report significant incidents swiftly.

Darktrace’s AI detects malicious activity as it happens and empowers customers to quickly understand the timeline of a compromise, as well as files accessed and exfiltrated by an attacker. This not only prepares organizations to resist the most sophisticated attacks, but also accelerates and radically simplifies the process of reporting the data breach.

Security teams should not have to confront disclosure processes on their own. Attacks happen fast, and their aftermaths are messy – retrospective investigation of lost data can be a futile effort with traditional approaches. With Darktrace, security teams can meet disruptive and sudden attacks with precise and nimble means of uncovering data, as well as detection and mitigation of risk. And, should the need arise, rapid and accurate reporting of events is laid out on a silver platter by the AI.

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
Justin Fier
SVP, Red Team Operations
Written by
Sally Kenyon Grant
VP, Darktrace Federal

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August 5, 2026

Testing a Prompt injection Attack Against an Enterprise AI Agent

prompt injectionDefault blog imageDefault blog image

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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About the author
Carlo Loregian
Solutions Engineer

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August 4, 2026

Extending AI Security Visibility with Darktrace and Microsoft Agent 365

microsoft darktrace integrationDefault blog imageDefault blog image

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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