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April 2, 2020

How AI Caught APT41 Exploiting Vulnerabilities

Analyzing how the cyber-criminal group APT41 exploited a zero-day vulnerability, we show how Darktrace’s AI detected and investigated the threat immediately.
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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02
Apr 2020

Executive summary

  • Darktrace detected several highly targeted attacks in early March, well before any associated signatures had become available. Two weeks later, the attacks were attributed to Chinese threat-actor APT41.
  • APT41 exploited the Zoho ManageEngine zero-day vulnerability CVE-2020-10189. Darktrace automatically detected and reported on the attack in its earliest stages, enabling customers to contain the threat before it could make an impact.
  • The intrusions described here were part of a wider campaign aiming to gain initial access to as many companies as possible during the window of opportunity presented by CVE-2020-10189.
  • The reports generated by Darktrace highlighted and delineated every aspect of the incident in the form of a meaningful security narrative. Even a junior responder could have reviewed this output and acted on this zero-day APT attack in under 5 minutes.

Fighting APT41’s global attack

In early March, Darktrace detected several advanced attacks targeting customers in the US and Europe. A majority of these customers are in the legal sector. The attacks shared the same Techniques, Tools & Procedures (TTPs), targeting public-facing servers and exploiting recent high-impact vulnerabilities. Last week, FireEye attributed this suspicious activity to the Chinese cyber espionage group APT41.

This campaign used the Zoho ManageEngine zero-day vulnerability CVE-2020-10189 to get access to various companies, but little to no follow-up was detected after initial intrusion. This activity indicates a broad-brush campaign to get initial access to as many target companies as possible during the zero-day window of opportunity.

The malicious activity observed by Darktrace took place late on Sunday March 8, 2020 and in the morning of March 9, 2020 (UTC), broadly in line with office hours previously attributed to the Chinese cyber espionage group APT41.

The graphic below shows an exemplary timeline from one of the customers targeted by APT41. The attacks observed in other customer environments are identical.

Timeline of the APT41 attack
Figure 1: A timeline of the attack

Technical analysis

The attack described here centered around the Zoho ManageEngine zero-day vulnerability CVE-2020-10189. Most of the attack appears to have been automated.

We observed the initial intrusion, several follow-up payload downloads, and command and control (C2) traffic. In all cases, the activity was contained before any later steps in the attack lifecycle, such as lateral movement or data exfiltration, were identified.

The below screenshot shows an overview of the key AI Analyst detections reported. Not only did it report on the SSL and HTTP C2 traffic, but it also reported on the payload downloads:

Cyber AI Analyst breaks down the APT41 attack
Figure 2: SSL C2 detection by Cyber AI Analyst
Figure 3: Payload detection by Cyber AI Analyst

Initial compromise

The initial compromise began with the successful exploitation of the Zoho ManageEngine zero-day vulnerability CVE-2020-10189. Following the initial intrusion, the Microsoft BITSAdmin command line tool was used to fetch and install a malicious Batch file, described below:

install.bat (MD5: 7966c2c546b71e800397a67f942858d0) from infrastructure 66.42.98[.]220 on port 12345.

Source: 10.60.50.XX
Destination: 66.42.98[.]220
Destination Port: 12345
Content Type: application/x-msdownload
Protocol: HTTP
Host: 66.42.98[.]220
URI: /test/install.bat
Method: GET
Status Code: 200

Figure 4: Outbound connection fetching batch file

Shortly after the initial compromise, the first stage Cobalt Strike Beacon LOADER was downloaded.

Cobalt Strike Beacon loader screenshot
Figure 5: Detection of the Cobalt Strike Beacon LOADER

Command and Control traffic

Interestingly, TeamViewer activity and the download of Notepad++ was taking place at the same time as the C2 traffic was starting in some of the customer attacks. This indicates APT41 trying to use familiar tools instead of completely ‘Living off the Land’.

Storesyncsvc.dll was a Cobalt Strike Beacon implant (trial-version) which connected to exchange.dumb1[.]com. A successful DNS resolution to 74.82.201[.]8 was identified, which Darktrace discerned as a successful SSL connection to a hostname with Dynamic DNS properties.

Multiple connections to exchange.dumb1[.]com were identified as beaconing to a C2 center. This C2 traffic to the initial Cobalt Strike Beacon was leveraged to download a second stage payload.

Interestingly, TeamViewer activity and the download of Notepad++ was taking place at the same time as the C2 traffic was starting in some of the customer attacks. This indicates APT41 trying to use familiar tools instead of completely ‘Living off the Land’. There is at least high certainty that the use of these two tools can be attributed to this intrusion instead of regular business activity. Notepad++ was not normally used in the target customers’ environments, nor was TeamViewer – in fact, the use of both applications was 100% unusual for the targeted organizations.

Attack tools download

CertUtil.exe, a command line program installed as part of Certificate Services, was then leveraged to connect externally and download the second stage payload.

Detection associated with Meterpreter activity

Figure 6: Darktrace detecting the usage of CertUtil

A few hours after this executable download, the infected device made an outbound HTTP connection requesting the URI /TzGG, which was identified as Meterpreter downloading further shellcode for the Cobalt Strike Beacon.

Figure 7: Detection associated with Meterpreter activity. No lateral movement or significant data exfiltration was observed.

How Cyber AI Analyst reported on the zero-day exploit

Darktrace not only detected this zero-day attack campaign, but Cyber AI Analyst also saved security teams valuable time by investigating disparate security events and generating a report that immediately put them in a position to take action.

The below screenshot shows the AI Analyst incidents reported in one infected environment, over the eight days covering the intrusion period. The first incident on the left represents the APT activity described here. The other five incidents are independent of the APT activity and not as severe.

AI Analyst Security Incidents
Figure 8: The security incidents surfaced by AI Analyst

AI Analyst reported on six incidents in total over the eight-day period. Each AI Analyst incident includes a detailed timeline and summary of the incident, in a concise format that takes an average of two minutes to review. This means that with Cyber AI Analyst, even a non-technical person could have actioned a response to this sophisticated, zero-day incident in less than five minutes.

Conclusion

Without public Indicators of Compromise (IoCs) or any open-source intelligence available, targeted attacks are incredibly difficult to detect. Moreover, even the best detections are useless if they cannot be actioned by a security analyst at an early stage. Too often this occurs because of an overwhelming volume of alerts, or simply because the skills barrier to triage and investigation is too high.

This appears to be a broad campaign to gain initial access to many different companies and sectors. While very sophisticated in nature, the threat sacrificed stealth for speed by targeting many companies at the same time. APT41 wanted to utilize the limited window of opportunity that the Zoho zero-day provided before IT staff starts patching.

Darktrace’s Cyber AI is specifically designed to detect the subtle signs of targeted, unknown attacks at an early stage, without relying on prior knowledge or IoCs. It achieves this by continuously learning the normal patterns of behavior for every user, device, and associated peer group from scratch, and ‘on the job’.

In the face of this zero-day attack campaign, the AI’s ability to (a) detect unknown threats with self-learning AI and (b) augment strained responders with AI-driven investigations and reporting proved crucial. Indeed, it ensured that the attacks were swiftly contained before escalating to the later stages of the attack lifecycle.

Indicators of Compromise

Selection of Darktrace model breaches:

  • Anomalous File / Script from Rare External
  • Anomalous File / EXE from Rare External Location
  • Compromise / SSL to DynDNS
  • Compliance / CertUtil External Connection
  • Anomalous Connection / CertUtil Requesting Non Certificate
  • Anomalous Connection / CertUtil to Rare Destination
  • Anomalous Connection / New User-Agent to IP Without Hostname
  • Device / Initial Breach Chain Compromise
  • Compromise / Slow Beaconing Activity To External Rare
  • Compromise / Beaconing Activity To External Rare
  • Anomalous File / Numeric Exe Download
  • Device / Large Number of Model Breaches
  • Anomalous Server Activity / Rare External from Server
  • Compromise / Sustained TCP Beaconing Activity To Rare Endpoint
  • Compliance / Remote Management Tool On Server

The below screenshot shows Darktrace model breaches occurring together during the compromise of one customer:

Figure 9: Darktrace model breaches occurring together

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

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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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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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