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March 5, 2019

The VR Goldilocks Problem and Value of Continued Recognition

Security and Operations Teams face challenges when it comes to visibility and recognition. Learn more about how we find a solution to the problems!
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
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05
Mar 2019

First, some context about VR

Security Operations teams face two fundamental challenges when it comes to 'finding bad'.

The first is gaining and maintaining appropriate visibility into what is happening in our environments. Visibility is provided through data (e.g. telemetry, logs). The trinity of data sources for visibility concern accounts/credentials, devices, and network traffic.

The second challenge is getting good recognition within the scope of what is visible. Recognition is fundamentally about what alerting and workflows you can implement and automate in response to activity that is suspicious or malicious.

Visibility and Recognition each have their own different associated issues.

Visibility is a problem about what is and can be generated and either read as telemetry, or logged and stored locally, or shipped to a central platform. The timelines and completeness of what visibility you have can depend on factors such as how much data you can or can't store locally on devices that generate data - and for how long; what your data pipeline and data platform look like (e.g. if you are trying to centralise data for analysis); or the capability of host software agents you have to process certain information locally.

The constraints on visibility sets the bar for factors like coverage, timelines and completeness of what recognition you can achieve. Without visibility, we cannot recognize at all. With limited visibility, what we can recognize may not have much value. With the right visibility, we can still fail to recognise the right things. And with too much recognition, we can quickly overload our senses.

A good example of a technology that offers the opportunity to solve these challenges at the network layer is Darktrace. Their technology provides visibility, from a network traffic perspective, into data that concerns devices and the accounts/credentials associated with them. They then provide recognition on top of this by using Machine Learning (ML) models for anomaly detection. Their models alert on a wide range of activities that may be indicative of threat activity, (e.g. malware execution and command and control, a technical exploit, data exfiltration and so on).

The major advantage they provide, compared to traditional Intrusion Detection Systems (IDS) and other vendors who also use ML for network anomaly detection, is that you can a) adjust the sensitivity of their algorithms and b) build your own recognition for particular patterns of interest. For example, if you want to monitor what connections are made to one or two servers, you can set up alerts for any change to expected patterns. This means you can create and adjust custom recognition based on your enterprise context and tune it easily in response to how context changes over time.

The Goldilocks VR Matrix

Below is what we call the VR Goldilocks Matrix at PBX Group Security. We use it to assess technology, measure our own capability and processes, and ask ourselves hard questions about where we need to focus to get the most value from our budget, (or make cuts / shift investment) if we need to.

In the squares are some examples of what you (maybe) should think about doing if you find yourself there.

Important questions to ask about VR

One of the things about Visibility and Recognition is that it’s not a given they are ‘always on’. Sometimes there are failure modes for visibility (causing a downstream issue with recognition). And sometimes there are failure modes or conditions under which you WANT to pause recognition.

The key questions you must have answers to about this include:

  • Under what conditions might I lose visibility?
  • How would I know if I have?
  • Is that loss a blind spot (i.e. data is lost for a given time period)…
  • …or is it 'a temporal delay’ (e.g. a connection fails and data is batched for moving from A to B but that doesn’t happen for a few hours)?
  • What are the recognitions that might be impacted by either of the above?
  • What is my expectation for the SLA on those recognitions from ‘cause of alert’ to ‘response workflow’?
  • Under what conditions would I be willing to pause recognition, change the workflow for what happens upon recognition, or stop it all together?
  • What is the stacked ranked list of ‘must, should, could’ for all recognition and why?

Alerts. Alerts everywhere.

More often than not, Security Operations teams suffer the costs of wasted time due to noisy alerts from certain data sources. As a consequence, it's more difficult for them to single out malicious behavior as suspicious or benign. The number of alerts that are generated due to out of the box SIEM platform configurations for sources like Web Proxies and Domain Controllers are often excessive, and the cost to tune those rules can also be unpalatable. Therefore, rather than trying to tune alerts, teams might make a call to switch them off until someone can get around to figuring out a better way. There’s no use having hypothetical recognition, but no workflow to act on what is generate (other than compliance).

This is where technologies that use ML can help. There are two basic approaches...

One is to avoid alerting until multiple conditions are met that indicate a high probability of threat activity. In this scenario, rather than alerting on the 1st, 2nd, 3rd and 4th ‘suspicious activities’, you wait until you have a critical mass of indicators, and then you generate one high fidelity alert that has a much greater weighting to be malicious. This requires both a high level of precision and accuracy in alerting, and naturally some trade off in the time that can pass before an alert for malicious activity is generated.

The other is to alert on ‘suspicious actives 1-4' and let an analyst or automated process decide if this merits further investigation. This approach sacrifices accuracy for precision, but provides rapid context on whether one, or multiple, conditions are met that push the machine(s) up the priority list in the triage queue. To solve for the lower level of accuracy, this approach can make decisions about how long to sustain alerting. For example, if a host triggers multiple anomaly detection models, rather than continue to send alerts (and risk the SOC deciding to turn them off), the technology can pause alerts after a certain threshold. If a machine has not been quarantined or taken off the network after 10 highly suspicious behaviors are flagged, there is a reasonable assumption that the analyst will have dug into these and found the activity is legitimate.

Punchline 1: the value of Continued Recognition even when 'not malicious'

The topic of paused detections was raised after a recent joint exercise between PBX Group Security and Darktrace in testing Darktrace’s recognition. After a machine being used by the PBX Red Team breached multiple high priority models on Darktrace, the technology stopped alerting on further activity. This was because the initial alerts would have been severe enough to trigger a SOC workflow. This approach is designed to solve the problem of alert overload on a machine that is behaving anomalously but is not in fact malicious. Rather than having the SOC turn off alerts for that machine (which could later be used maliciously), the alerts are paused.

One of the outcomes of the test was that the PBX Detect team advised they would still want those alerts to exist for context to see what else the machine does (i.e. to understand its pattern of life). Now, rather than pausing alerts, Darktrace is surfacing this to customers to show where a rule is being paused and create an option to continue seeing alerts for a machine that has breached multiple models.

Which leads us on to our next point…

Punchline 2: the need for Atomic Tests for detection

Both Darktrace and Photobox Security are big believers in Atomic Red Team testing, which involves ‘unit tests’ that repeatedly (or at a certain frequency) test a detection using code. Unit tests automate the work of Red Teams when they discovery control strengths (which you want to monitor continuously for uptime) or control gaps (which you want to monitor for when they are closed). You could design atomic tests to launch a series of particular attacks / threat actor actions from one machine in a chained event. Or you could launch different discreet actions from different machines, each of which has no prior context for doing bad stuff. This allows you to scale the sample size for testing what recognition you have (either through ML or more traditional SIEM alerting). Doing this also means you don't have to ask Red Teams to repeat the same tests again, allowing them to focus on different threat paths to achieve objectives.

Mitre Att&ck is an invaluable framework for this. Many vendors are now aligning to Att&ck to show what they can recognize relating to attack TTPs (Tools, Tactics and Procedures). This enables security teams to map what TTPs are relevant to them (e.g. by using threat intel about the campaigns of threat actor groups that are targeting them). Atomic Red Team tests can then be used to assure that expected detections are operational or find gaps that need closing.

If you miss detections, then you know you need to optimise the recognition you have. If you get too many recognitions outside of the atomic test conditions, you either have to accept a high false positive rate because of the nature of the network, or you can tune your detection sensitivity. The opportunities to do this with technology based on ML and anomaly detection are significant, because you can quickly see for new attack types what a unit test tells you about your current detections and that coverage you think you have is 'as expected'.

Punchline 3: collaboration for the win

Using well-structured Red Team exercises can help your organisation and your technology partners learn new things about how we can collectively find and halt evil. They can also help defenders learn more about good assumptions to build into ML models, as well as covering edge cases where alerts have 'business intelligence' value vs ‘finding bad’.

If you want to understand the categorisations of ways that your populations of machines act over time, there is no better way to do it than through anomaly detection and feeding alerts into a system that supports SOC operations as well as knowledge management (e.g. a graph database).

Working like this means that we also help get the most out of the visibility and recognition we have. Security solutions can be of huge help to Network and Operations teams for troubleshooting or answering questions about network architecture. Often, it’s just a shift in perspective that unlocks cross-functional value from investments in security tech and process. Understanding that recognition doesn’t stop with security is another great example of where technologies that let you build your own logic into recognition can make a huge difference above protecting the bottom line, to adding top line value.

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

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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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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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