Improve Security with Attack Path Modeling

Learn how to prioritize vulnerabilities effectively with attack path modeling. Learn from Darktrace experts and stay ahead of cyber threats.
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
Max Heinemeyer
Global Field CISO
Written by
Adam Stevens
Senior Director of Product, Cloud | Darktrace
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09
Aug 2023

TLDR: There are too many technical vulnerabilities and there is too little organizational context for IT teams to patch effectively. Attack path modelling provides the organizational context, allowing security teams to prioritize vulnerabilities. The result is a system where CVEs can be parsed in, organizational context added, and attack paths considered, ultimately providing a prioritized list of vulnerabilities that need to be patched.

Figure 1: The Darktrace user interface presents risk-prioritized vulnerabilities


This blog post explains how Darktrace addresses the challenge of vulnerability prioritization. Most of the industry focusses on understanding the technical impact of vulnerabilities globally (‘How could this CVE generally be exploited? Is it difficult to exploit? Are there pre-requisites to exploitation? …’), without taking local context of a vulnerability into account. We’ll discuss here how we create that local context through attack path modelling and map it to technical vulnerability information. The result is a stunningly powerful way to prioritize vulnerabilities.

We will explore:

1)    The challenge and traditional approach to vulnerability prioritization
2)    Creating local context through machine learning and attack path modelling
3)    Examining the result – contextualized, vulnerability prioritization

The Challenge

Anyone dealing with Threat and Vulnerability Management (TVM) knows this situation:

You have a vulnerability scanning report with dozens or hundreds of pages. There is a long list of ‘critical’ vulnerabilities. How do you start prioritizing these vulnerabilities, assuming your goal is reducing the most risk?

Sometimes the challenge is even more specific – you might have 100 servers with the same critical vulnerability present (e.g. MoveIT). But which one should you patch first, as all of those have the same technical vulnerability priority (‘critical’)? Which one will achieve the biggest risk reduction (critical asset e.g.)? Which one will be almost meaningless to patch (asset with no business impact e.g.) and thus just a time-sink for the patch and IT team?

There have been recent improvements upon flat CVE-scoring for vulnerability prioritization by adding threat-intelligence about exploitability of vulnerabilities into the mix. This is great, examples of that additional information are Exploit Prediction Scoring System (EPSS) and Known Exploited Vulnerabilities Catalogue (KEV).

Figure 2: The idea behind EPSS – focus on actually exploited CVEs. (diagram taken from https://www.first.org/epss/model)

With CVE and CVSS scores we have the theoretical technical impact of vulnerabilities, and with EPSS and KEV we have information about the likelihood of exploitation of vulnerabilities. That’s a step forward, but still doesn’t give us any local context. Now we know even more about the global and generic technical risk of a vulnerability, but we still lack the local impact on the organization.

Let’s add that missing link via machine learning and attack path modelling.

Adding Attack Path Modelling for Local Context

To prioritize technical vulnerabilities, we need to know as much as we can about the asset on which the vulnerability is present in the context of the local organization. Is it a crown jewel? Is it a choke point? Does it sit on a critical attack path? Is it a dead end, never used and has no business relevance? Does it have organizational priority? Is the asset used by VIP users, as part of a core business or IT process? Does it share identities with elevated credentials? Is the human user on the device susceptible to social engineering?

Those are just a few typical questions when trying to establish local context of an asset. Knowing more about the threat landscape, exploitability, or technical information of a CVE won’t help answer any of the above questions. Gathering, evaluating, maintaining, and using this local context for vulnerability prioritization is the hard part. This local context often resides informally in the head of the TVM or IT team member, having been assembled by having been at the organization for a long time, ‘knowing’ systems, applications and identities in question and talking to asset and application owners if time permits. This does unfortunately not scale, is time-consuming and heavily dependent on individuals.

Understanding all attack paths for an organization provides this local context programmatically.

We discover those attack paths, and these are bespoke for each organization through Darktrace PREVENT, using the following method (simplified):

1)    Build an adaptive model of the local business. Collect, combine, and analyze (using machine learning and non-machine learning techniques) data from various data domains:

a.     Network, Cloud, IT, and OT data (network-based attack paths, communication patterns, peer-groups, choke-points, …). Natively collected by Darktrace technology.

b.     Email data (social engineering attack paths, phishing susceptibility, external exposure, security awareness level, …). Natively collected by Darktrace technology.

c.     Identity data (account privileges, account groups, access levels, shared permissions, …). Collected via various integrations, e.g. Active Directory.

d.     Attack surface data (internet-facing exposure, high-impact vulnerabilities, …). Natively collected by Darktrace technology.

e.     SaaS information (further identity context). Natively collected by Darktrace

f.      Vulnerability information (CVEs, CVSS, EPSS, KEV, …). Collected via integrations, e.g. Vulnerability Scanners or Endpoint products.

Figure 3: Darktrace PREVENT revealing each stage of an attack path

2)    Understand what ‘crown jewels’ are and how to get to them. Calculate entity importance (user, technical asset), exposure levels, potential damage levels (blast radius) weakness levels, and other scores to identify most important entities and their relationships to each other (‘crown jewels’).

Various forms of machine learning and non-machine learning techniques are used to achieve this. Further details on some of the exact methods can be found here. The result is a holistic, adaptive and dynamic model of the organization that shows most important entities and how to get to them across various data domains.

The combination of local context and technical context, around the severity and likelihood of exploitation, creates the Darktrace Vulnerability Score. This enables effective risk-based prioritisation of CVE patching.

Figure 4: List of devices with the highest damage potential in the organization - local context

3)    Map the attack path model of the organization to common cyber domain knowledge. We can then combine things like MITRE ATT&CK techniques with those identified connectivity patterns and attack paths – making it easy to understand which techniques, tools and procedures (TTPs) can be used to move through the organization, and how difficult it is to exploit each TTP.

Figure 5: An example attack path with associated MITRE techniques and difficulty scores for each TTP

We can now easily start prioritizing CVE patching based on actual, organizational risk and local context.

Bringing It All Together

Finally, we overlay the attack paths calculated by Darktrace with the CVEs collected from a vulnerability scanner or EDR. This can either happen as a native integration in Darktrace PREVENT, if we are already ingesting CVE data from another solution, or via CSV upload.

Figure 6: Darktrace's global CVE prioritization in action.

But you can also go further than just looking at the CVE that delivers the biggest risk reduction globally in your organization if it is patched. You can also look only at certain group of vulnerabilities, or a sub-set of devices to understand where to patch first in this reduced scope:

Figure 7: An example of the information Darktrace reveals around a CVE

This also provides the TVM team clear justification for the patch and infrastructure teams on why these vulnerabilities should be prioritized and what the positive impact will be on risk reduction.

Attack path modelling can be utilized for various other use cases, such as threat modelling and improving SOC efficiency. We’ll explore those in more depth at a later stage.

Want to explore more on using machine learning for vulnerability prioritization? Want to test it on your own data, for free? Arrange a demo today.

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
Max Heinemeyer
Global Field CISO
Written by
Adam Stevens
Senior Director of Product, Cloud | Darktrace

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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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