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April 23, 2021

Darktrace Identifies APT35 in Pre-Infected State

Learn how Darktrace identified APT35 (Charming Kitten) in a pre-infected environment. Gain insights into the detection and mitigation of this threat.
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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23
Apr 2021

What is APT35?

APT35, sometimes referred to as Charming Kitten, Imperial Kitten, or Tortoiseshell, is a notorious cyber-espionage group which has been active for nearly 10 years. Famous for stealing scripts from HBO’s Game of Thrones in 2017 and suspected of interfering in the U.S. presidential election last year, it has launched extensive campaigns against organizations and officials across North America and the Middle East. Public attribution has associated APT35 with an Iran-based nation state threat actor.

Darktrace regularly detects attacks by many known threat actors including Evil Corp and APT41, alongside large amounts of malicious but uncategorized activity from sophisticated attack groups. As Cyber AI doesn’t rely on pre-defined rules, signatures, or threat intelligence to detect cyber-attacks, it often detects new and previously unknown threats.

This blog post examines a real-world instance of APT35 activity in an organization in the EMEA region. Darktrace observed this activity last June, but due to ongoing investigations, details are only now being released with the wider community. It represents an interesting case for the value of self-learning AI in two key ways:

  • Identifying ‘low and slow’ attacks: How do you spot an attacker that is lying low and conducts very little detectable activity?
  • Detecting pre-existing infections without signatures: What if a threat actor is already inside the system when Cyber AI is activated?

Advanced Persistent Threats (APTs) lying low

APT35 had already infected a single corporate device, likely via a spear phishing email, when Cyber AI was deployed in the company’s digital estate for the first time.

The infected device exhibited no other signs of malicious activity beyond continued command and control (C2) beaconing, awaiting instructions from the attackers for several days. This is what we call ‘lying low’ – where the hacker stays present within a system, but remains under the radar, avoiding detection either intentionally, or because they’re focusing on another victim while being content with backdoor access into the organization.

Either way, this is a nightmare scenario for a security team and any security vendor: an APT which has established a foothold and is lying in wait to continue their attack – undetected.

Finding the infected device

When Darktrace’s AI was first activated, it spent five business days learning the unique ‘patterns of life’ for the organization. After this initial, short learning period, Darktrace immediately flagged the infected device and the C2 activity.

Although the breach device had been beaconing since before Darktrace was implemented, Cyber AI automatically clusters devices into ‘peer groups’ based on similar behavioral patterns, enabling Darktrace to identify the continued C2 traffic coming from the device as highly unusual in comparison to the wider, automatically identified peer group. None of its behaviorally close neighbors were doing anything remotely similar, and Darktrace was therefore able to determine that the activity was malicious, and that it represented C2 beaconing.

Darktrace detected the APT35 C2 activity without the use of any signatures or threat intelligence on multiple levels. Responding to the alerts, the internal security team quickly isolated the device and verified with the Darktrace system that no further reconnaissance, lateral movement, or data exfiltration had taken place.

APT35 ‘Charming Kitten’ analysis

Once the C2 was detected, Cyber AI Analyst immediately began analyzing the infected device. The Cyber AI Analyst only highlights the most severe incidents in any given environment and automates many of the typical level one and level two SOC tasks. This includes reviewing all alerts, investigating the scope and nature of each event, and reducing time to triage by 92%.

Figure 1: Similar Cyber AI Analyst report observing C2 communications

Numerous factors made the C2 activity stand out strongly to Darktrace. Combining all those small anomalies, Darktrace was able to autonomously prioritize this behavior and classify it as the most significant security incident in the week.

Figure 2: Example list of C2 detections for an APT35 attack

Some of the command and control destinations were known to threat intelligence and open-source intelligence (OSINT) – for instance, the domain cortanaservice[.]com is a known C2 domain for APT35.

However, the presence of a known malicious domain does not guarantee detection. In fact, the organization had a very mature security stack, yet they failed to discover the existing APT35 infection until Darktrace was activated in their environment.

Assessing the impact of the intrusion

Once an intrusion has been identified, it is important to understand the extent of it – such as whether lateral movement is occurring and what connectivity the infected device has in general. Asset management is never perfect, so it can be very hard for organizations to determine what damage a compromised device is capable of inflicting.

Darktrace presents this information in real time, and from a bird’s-eye perspective, making the assessment very simple. It immediately highlights which subnet the device is located in and any further context.

Figure 3: Darktrace’s Threat Visualizer displaying the connectivity of a device

Based on this information, the organization confirmed that it was a corporate device that had been infected by APT35. As Darktrace shows any credentials associated with the device, a quick assessment could be made of potentially compromised accounts.

Figure 4: Similar and associated credentials of a device

Luckily, only a single local user account was associated with the device.

The exact level of privileges and connectivity which the infected device had, as well as the extent to which the intrusion might have spread from the initially infected device, was still uncertain. By looking at the device’s event log, this became rapidly clear within minutes.

Filtering first for internal connections only (excluding any connections going to the Internet) gave a good idea of the level of connectivity of the device. A cursory glance showed that the device did indeed have some level of internal connectivity. It made DNS requests to the internal domain controller and was making successful NetBIOS connections over ports 135 and 139 internally.

By filtering further in the event log, it quickly became clear that in this time the device had not used any administrative channels, such as RDP, SSH, Telnet, or SMB. This is a strong indicator that no lateral movement over common channels had taken place.

It is more difficult to assess whether the device was performing any other suspicious activity, like stealthy reconnaissance or staging data from other internal devices. Darktrace provided another capability to assess this quickly – filtering the device’s network connections to show only unusual or new connections.

Figure 5: Event device log filtered to show unusual connections only

Darktrace assesses each individual connection for every entity observed in context, using its unsupervised machine learning to evaluate how unusual a given connection is. This could be a single new failed internal connection attempt, indicating stealthy reconnaissance, or a connection over SMB at an unusual time to a new internal destination, implying lateral movement or data staging.

By filtering for only unusual or new connections, Darktrace’s AI produces further leads that can be pursued extremely quickly, thanks to the context and added visibility.

No further suspicious internal connections were observed, strengthening the hypothesis that APT35 was lying low at that time.

Unprecedented but not unpreventable

Darktrace’s 24/7 monitoring service, Proactive Threat Notifications, would have alerted on and escalated the incident. Darktrace RESPOND would have responded autonomously and enforced normal activity for the device, preventing the C2 traffic without interrupting regular business workflows.

It is impossible to predefine where the next attack will come from. APT35 is just one of the many sophisticated threat actors on the scene, and with such a diverse and volatile threat landscape, unsupervised machine learning is crucial in spotting and defending against anomalies, no matter what form they take.

This case study helps illustrate how Darktrace detects pre-existing infections and ‘low and slow’ attacks, and further shows how Darktrace can be used to quickly understand the scope and extent of an intrusion.

Learn how Cyber AI Analyst detected APT41 two weeks before public attribution

Shortened list of C2 detections over four days on the infected device:

  • Compromise / Sustained TCP Beaconing Activity To Rare Endpoint
  • Compromise / Beaconing Meta Model
  • Compromise / Beaconing Activity To External Rare
  • Compromise / SSL Beaconing To Rare Destination
  • Compromise / Slow Beaconing To External Rare
  • Compromise / High Volume of Connections with Beacon Score
  • Compromise / Unusual Connections to Rare Lets Encrypt
  • Compromise / Beacon for 4 Days
  • Compromise / Agent Beacon

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

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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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