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July 15, 2021

Darktrace Detects Egregor Ransomware in Customer Environment

See how Darktrace managed to detect and eliminate an Egregor ransomware extortion attack in a customer environment without the use of any signatures.
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
Justin Fier
SVP, Red Team Operations
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15
Jul 2021

Ransomware groups are coming and going faster than ever. In June alone we saw Avaddon release its decryption keys unprompted and disappear from sight, while members of CLOP were arrested in Ukraine. The move follows increasing pressure from the US intelligence community and Ukrainian authorities, who took down Egregor ransomware back in February. Egregor had only been around since September 2020. It survived less than six months.

But these gangs aren’t going away – they are simply going underground. Despite ‘closures’, cases of ransomware continue to rise and new threat actors and independent hackers pop up on the Dark Web every day.

As malware actors lay low and resurface with new variants, keeping up with the stream of signatures and new strains has become untenable. This blog studies the techniques, tools and procedures (TTPs) observed from a real-life Egregor intrusion last autumn, which showcases how Self-Learning AI detected the attack without relying on signatures.

Egregor: Maze reloaded

150 companies
worldwide have fallen victim to Egregor.

Law enforcement authorities have been busy this year. Aside from Egregor and CLOP, actions were taken against Netwalker in Bulgaria and the US, while Europol announced that an international operation had disrupted the core infrastructure of Emotet, one of the most prominent botnets of the past decade.

All parties – from governments down to individual businesses – are taking the threat of ransomware more seriously. In response to this added pressure, cyber-criminals often prefer to shut up shop rather than hang around long enough to be arrested.

DarkSide famously closed down after the Colonial Pipeline attacks, only nine months after it had been created. An admin from the Ziggy gang announced that it would issue refunds and was looking for a job as a threat hunter.

“Hi. I am Ziggy ransomware administrator. We decided to publish all decryption keys.

We are very sad about what we did. As soon as possible, all the keys will be published in this channel.”

Take this apology with a pinch of salt. The players which have ‘closed down’ have not had a change of heart, they’ve just changed tack. Different names and new infrastructure can help keep the heat off and circumvent US sanctions or federal scrutiny. PayloadBIN (a new ransomware which cropped up last month), WastedLocker, Dridex, Hades, Phoenix, Indrik Spider… all just aliases for one single group: Evil Corp.

The FBI are becoming more aggressive in their methods of infiltration and disruption, so it is likely we will see more of these U-turns and guerrilla-style tactics. Temporary pop-up gangs are an emerging trend in place of large, established enterprises like REvil, whose websites also vanished following the attack against Kaseya. And there is no doubt we will continue to witness these ‘exit scams’, where groups retire and re-brand, like Maze did last September, when it came back as Egregor.

Darktrace detects malware regardless of the name or strain. It stopped Maze last year, and, as we shall see below, it stopped its successor Egregor, even though the code and C2 endpoints used in the intrusion had never been seen before.

30%
of ransom profits are taken by Egregor developers.

Egregor ransomware attack

Back in November 2020, Egregor was in full bloom, targeting major organizations and exfiltrating data in ‘double extortion’ attacks. At a logistics company in Europe with around 20,000 active devices, during a Darktrace Proof of Value (POV) trial, Egregor struck.

Figure 1: Timeline of the attack. The overall dwell time — from first C2 connection to encryption — was five days.

As a Ransomware-as-a-Service (RaaS) gang, it appears Egregor had partnered with botnet providers to facilitate initial access. In this case, the compromised device carried signs of prior infection. It was seen connecting to an apparent Webex endpoint, before connecting to the Akamai doppelganger, amajai-technologies[.]network. This activity was followed by a number of command and control (C2) and exfiltration-related breaches.

Three days later, Darktrace observed lateral movement over HTTPS. Another device – a server – was seen connecting to the amajai host. This server wrote unusual numeric exectuables to shared SMB drives and took new service control. A third host then made a ~50GB upload to a rare IP.

Figure 2: Cyber AI Analyst summarizes the initial C2 and unusual SMB writes in a similar incident, followed later by a large upload to a rare external endpoint.

After two days, encryption began. This triggered multiple hosts breaches. On the final day, the attacker made large uploads to various endpoints, all from ostensibly compromised hosts.

Retrospective analysis

$4m
is the highest recorded cost of an Egregor ransom.

If the attack had not been neutralized at this point, it could have resulted in significant financial loss and reputational damage for the company. The two-pronged attack enabled Egregor both to encrypt critical resources and to exfiltrate them, with a view to publicizing sensitive data if the victims refused to pay up.

The affiliates who deployed the ransomware in this case were highly skilled. They leveraged a number of sophisticated techniques including the use of a large number of C2 endpoints, with doppelgangers and off-the-shelf tools.

The adoption of HTTPS for lateral movement and reconnaissance reduced lateral noise for scans and enumeration. The complex C2 had numerous endpoints, some of which were doppelgangers of legitimate sites. Furthermore, some malware was downloaded as masqueraded files: the mimetype Octet Streams were downloaded as ‘g.pixel’. These three tactics helped obfuscate the attacker’s movements and trick traditional security tools.

Ransomware attacks are occurring at a speed that even five years ago was unimaginable. In this case, the overall dwell time was less than a week, and part of the attack happened out of office hours. This highlights the need for Autonomous Response, which can keep up with novel threats and does not rely on humans being in the loop to contain cyber-attacks.

Gone today, here tomorrow

Egregor was busted in February, but we may well see it resurface under a different name and with modified code. If and when this happens, signatures will be of no use. Catching never-before-seen ransomware, which employs novel methods of intrusion and extortion, requires a different approach.

The endpoint in the case study above is now associated via open-source intelligence (OSINT) with Cobalt Strike. But at the time of the investigation, the C2 was unlisted. Similarly, the malware was unknown to OSINT and thus evaded signature-based tools.

Despite this, Self-Learning AI detected every single stage of the in-progress attack. No action was taken as it was only a trial POV so Darktrace had no remote access in the environment. However, after seeing the power of the technology, the organization decided to implement Darktrace across its digital estate.

Thanks to Darktrace analyst Roberto Romeu for his insights on the above threat find.

Learn how Darktrace stops Egregor and all forms of ransomware

Darktrace model detections:

  • Agent Beacon to New Endpoint
  • Agent Beacon (Long Period)
  • Agent Beacon (Medium Period)
  • Agent Beacon (Short Period)
  • Anomalous Octet Stream
  • Anomalous Server Activity / Outgoing from Server
  • Anomalous SMB Followed By Multiple Model Breaches
  • Anomalous SSL without SNI to New External
  • Beaconing Activity To External Rare
  • Beacon to Young Endpoint
  • Data Sent To New External Device
  • Data Sent to Rare Domain
  • DGA Beacon
  • Empire Python Activity Pattern
  • EXE from Rare External Location
  • High Volume of Connections with Beacon Score
  • High Volume of New or Uncommon Service Control
  • HTTP Beaconing to Rare Destination
  • Large Number of Model Breaches
  • Long Agent Connection to New Endpoint
  • Low and Slow Exfiltration
  • Multiple C2 Model Breaches
  • Multiple Connections to New External TCP Port
  • Multiple Failed Connections to Rare Endpoint
  • Multiple Lateral Movement Model Breaches
  • Network Scan
  • New Failed External Connections
  • New or Uncommon Service Control
  • Numeric Exe in SMB Write
  • Rare External SSL Self-Signed
  • Slow Beaconing Activity To External Rare
  • SMB Drive Write
  • SMB Enumeration
  • SSL Beaconing to Rare Destination
  • SSL or HTTP Beacon
  • Suspicious Beaconing Behaviour
  • Suspicious Self-Signed SSL
  • Sustained SSL or HTTP Increase
  • Quick and Regular Windows HTTP Beaconing
  • Uncommon 1 GiB Outbound
  • Unusual BITS Activity
  • Unusual Internal Connections
  • Unusual SMB Version 1 Connectivity
  • Zip or Gzip from Rare External Location

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
Justin Fier
SVP, Red Team Operations

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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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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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