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July 8, 2021

How Cyber-Attacks Take Down Critical Infrastructure

Cyber-attacks can bypass IT/OT security barriers and threaten your organization's infrastructure. Here's how you can stay protected in today's threat landscape.
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
Dr. Oakley Cox-Robinson
Senior Director of Product
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08
Jul 2021

Balancing Operational Continuity and Safety in Critical Infrastructure

The recent high-profile attacks against Colonial Pipeline and JBS Foods highlight that operational technology (OT) — the devices that drive gas flows and food processing, along with essentially all other machine-driven physical processes — does not need to be directly targeted in order to be shut down as the result of a cyber-attack.

Indeed, in the Colonial Pipeline incident, the information technology (IT) systems were reportedly compromised, with operations shut down intentionally out of an abundance of caution, that is, so as to not risk the attack spreading to OT and threatening safety. This highlights that threats to both human and environmental safety, along with uncertainty as to the scope of infection, present risk factors for these sensitive industrial environments.

Continuity through availability and integrity

In most countries, critical infrastructure (CI) — ranging from power grids and pipelines to transportation and health care — must maintain continuous activity. The recent ransomware attack against Colonial Pipeline demonstrates why this is the case, where gas shortages due to the compromise led to dangerous panic buys and long lines at the pumps.

Ensuring continuous operation of critical infrastructure requires safeguarding the availability and integrity of machinery. This means that organizations overseeing critical infrastructure must foresee any possible risks and implement systems, procedures, and technologies that mitigate or remove these risks so as to keep their operations running.

Operational demand versus safety

Alongside this requirement for operational continuity, and often in opposition to it, is the requirement for operational safety. These requirements can be in opposition because operational continuity demands that devices remain up and running at all costs, and operational safety demands that humans and the environment be protected at all costs.

Safety measures in critical infrastructure have improved and become increasingly prioritized over the last 50 years following numerous high-profile incidents, such as the Bhopal chemical disaster, the Texas City refinery explosion, and the Deepwater Horizon oil spill. Appropriate safety precautions could have likely prevented these incidents, but at the expense of operational continuity.

Consequently, administrators of critical infrastructure have to balance the very real threat that an incident may pose to both human life and the environment with the demand to remain operational at all times. More often than not, the final decision regarding what constitutes an acceptable risk is determined by budgets and cost-benefit analyses.

Cyber-attack: A rising risk profile for critical infrastructure

In 2010, the discovery of the Stuxnet malware — which resulted in a nuclear facility in Iran having its centrifuges ruined via compromised programmable logic controllers (PLCs) — demonstrated that critical infrastructure could be targeted by a cyber-attack.

At the time of Stuxnet, critical infrastructure industries used computers designed to ensure operational continuity with little regard for cyber security, as at the time the risk of a cyber-attack seemed either non-existent or vanishingly low. Since then, a number of attacks targeting industrial environments that have emerged on the global threat landscape.

Figure 1: An overview of distinctive methods used in attacks against industrial environments

Classic strains of industrial malware, such as Stuxnet, Triton, and Industroyer, have historically been installed via removable media, such as USB. This is because OT networks are traditionally segregated from the Internet in what is known as an ‘air gap.’ And this remains a prevalent vector of attack, with a study recently finding that cyber-threats installed via USB and other external media doubled in 2021, with 79% of these holding the potential to disrupt OT.

In many ways, operational demands in the subsequent 10 years have made critical infrastructure even more vulnerable. These include the convergence of information technology and operational technology (IT/OT convergence), the adoption of devices in the Industrial Internet of Things (IIoT), and the deprecation of manual back-up systems. This means that OT can be disrupted by cyber-attacks that first target IT systems, rather than having to be installed manually via external media.

At the same time, recent government initiatives — such as the Department of Energy’s 100-day ‘cyber sprint’ to protect electricity operations and President Biden’s Executive Order on Improving the Nation’s Cybersecurity — and regulatory frameworks and directives such as the EU’s NIS directive have either encouraged or mandated that critical infrastructure industries start addressing this new risk.

With the severe and persistent threat that cyber-attacks pose to critical infrastructure, including maritime cybersecurity, and the increasing calls to address the issue, the question remains as to how to best achieve robust cyber defense.

Assessing the risk

To claim administrators of critical infrastructure are ignorant or oblivious to the threat posed by cyber-attacks would be unfair. Many organizations have implemented changes to mitigate or remove the risk either as a result of regulation or their own forward thinking.

However, these projects can take years, even decades. High costs and ever-changing operational demand also mean that these projects may never fully remove the risk.

As a result, many operators may understand the threat of a cyber-attack but not be in a position to do anything about it in the short or medium term. Instead, procedures have to be put in place to minimize risk even if this threatens operational continuity.

For example, a risk assessment may decide it is best to shut down all OT operations in the event of a cyber-attack in order to avoid a major accident. This abundance of caution is forced upon operators, who do not have the ability to immediately confirm the boundaries of a compromise. The prevalence of cyber insurance provides this option with further appeal. Any losses incurred by stopping operations can theoretically be recouped and the risk is therefore transferred.

While the full details of the Colonial Pipeline ransomware incident are still to be determined, the sequence of events outlined below provides a plausible explanation for how a cyber-attack could take down critical infrastructure, even when that cyber-attack does not reach or even target OT systems. Indeed, the CEO of Colonial Pipeline, in a testimony to congress, confirmed “the imperative to isolate and contain the attack to help ensure the malware did not spread to the operational technology network, which controls our pipeline operations, if it had not already.”

Figure 2: A sequence of events which may lead to critical infrastructure being shut down by a cyber-attack, even when that cyber-attack doesn’t directly impact OT networks

The limits of securing IT or OT in isolation

The emergence of OT cyber security solutions in the last five years demonstrates that critical infrastructure industries are trying to find a way to address the risks posed by cyber-attacks. But these solutions have limited scope, as they assume IT and OT are separated and use legacy security techniques such as malware signatures and patch management.

The 2021 SANS ICS Security Summit highlighted how the OT security community suffers from a lack of visibility in knowing and understanding their networks. For many organizations, simply determining whether an unusual incident is an attack or the result of a software error is a challenge.

Given that most OT cyber-attacks actually start in IT networks before pivoting into OT, investing in an IT security solution rather than an OT-specific solution may at first seem like a better business decision. But IT solutions fall short if an attacker successfully pivots into the OT network, or if the attacker is a rogue insider who already has direct access to the OT network. A siloed approach to securing either IT or OT in isolation will thus fall short of the full scope needed to safeguard industrial systems.

It is clear that a mature security posture for critical infrastructure would include security solutions for both IT and OT. Even then, using separate solutions to protect the IT and OT networks is limited, as it presents challenges when defending network boundaries and detecting incidents when an attacker pivots from IT to OT. Under time pressure, a security team does not want changes in visibility, detection, language or interface while trying to determine whether a threat crossed the ‘boundary’ between IT and OT.

Separate solutions can also make detecting an attacker abusing traditional IT attack TTPs within an OT network much harder if the security team is relying on a purely OT solution to defend the OT environment. Examples of this include the abuse of IT remote management tools to affect industrial environments, such as in the suspected cyber-attack at the Florida water facility earlier this year. Cybersecurity for utilities is becoming increasingly important as these sectors face growing cyber threats that can disrupt essential services.

Using AI to minimize cyber risk and maximize cyber safety

In contrast, Darktrace AI is able to defend an entire cyber ecosystem estate, building a ‘pattern of life’ across IT and OT, as well as the points at which they converge. Consequently, cyber security teams can use a single pane of glass to detect and respond to cyber-attacks as they emerge and develop, regardless of where they are in the environment.

Use cases for Darktrace’s Self-Learning AI include containing pre-existing threats to maintain continuous operations. This was seen when Darktrace’s AI detected pre-existing infections and acted autonomously to contain the threat, allowing the operator to leave infected IIoT devices active while waiting for replacements. Darktrace can also thwart ransomware in IT before it can spread into OT, as when Darktrace detected a ransomware attack targeting a supplier for critical infrastructure in North America at its earliest stages.

Darktrace’s unified protection, including visibility and early detection of zero-days, empowers security teams to overcome uncertainty and make a confident decision not to shut down operations. Darktrace has already demonstrated this ability in the wild, and allows organizations to understand normal machine and human behavior in order to enforce this behavior, even in the face of an emerging cyber-attack.

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
Dr. Oakley Cox-Robinson
Senior Director of Product

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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

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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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