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November 30, 2020

Darktrace Cyber Analyst Investigates Sodinokibi Ransomware

Darktrace’s Cyber AI Analyst uncovers the intricate details of a Sodinokibi ransomware attack on a retail organization. Dive into this real-time incident.
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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30
Nov 2020

Sodinokibi is one of the most lucrative ransomware strains of 2020, with its creators, cyber-criminal gang REvil, recently claiming over $100 million in profits this year alone. The prevalent threat is known to wipe backup files, encrypt files on local shares and exfiltrate data.

Exfiltration before encryption is a technique being increasingly adopted by profit-seeking cyber-criminals, who can threaten to leak the stolen data should a target organization not comply with their demands. Sodinobiki also makes heavy use of code obfuscation and encryption techniques to evade detection by signature-based, anti-virus solutions.

Darktrace’s AI recently detected Sodinokibi targeting a retail organization in the US. Prior to this year, the company operated primarily face-to-face in physical stores, but have conducted the majority of their business in the digital realm since the onset of the pandemic.

Cyber AI Analyst automatically launched a full investigation into this incident in real time, as the attack was unfolding. The technology provided summary reports of the entire incident which the security team could immediately action for incident response. This blog explores its findings.

Sodinokibi timeline

Darktrace automatically investigated on the full scope of the Sodinokibi attack, with Cyber AI Analyst clearly identifying and summarising every stage of the attack lifecycle, which played out over the course of three weeks as below:

Figure 1: A timeline of the attack

Darktrace produced a large number of security-relevant anomalies associated with just three credentials, and displayed these along a common timeline shown below:

Figure 2: A timeline view of anomaly detections separated by users. Note the clusters of model breaches for the compromised credentials leading up to October 14.

While a human analyst might have been able to identify these unusual patterns and investigate what caused the clusters of anomalous activity, this process would have taken precious hours during a crisis. Cyber AI Analyst automatically performed the same analysis using supervised machine learning trained on Darktrace’s world-leading analysts, generating meaningful summaries of each stage of the event in real time, as the incident unfolded.

REvil ransomware attack

The following events occurred during a free trial period, and Darktrace was not being actively monitored. Its Autonomous Response technology, Darktrace Antigena, was installed in passive mode, and in the absence of automatic interference at an early stage, this compromise was allowed to unfold without interruption. However, with Darktrace’s AI learning normal ‘patterns of life’ for every device in the background, identifying anomalies, and launching an automated investigation into the attack, we are able to go back into the Threat Visualizer and see how the incident unfolded.

The attack began when the credentials of a highly privileged member of the retail organization’s IT team were compromised. REvil is known to make use of phishing emails, exploit kits, server vulnerabilities, and compromised MSP networks for initial intrusion.

In this case, the attacker used the IT credential to compromise a domain controller and exfiltrate data directly after initial reconnaissance. Darktrace’s AI detected the attacker logging into the domain controller via SMB, writing suspicious files and then deleting batch scripts and log files in the root directory to clear their tracks.

The domain controller then made connections to several rare external endpoints, and Darktrace witnessed a 28MB upload that was likely exfiltration of initial reconnaissance data. Four days later, the attacker connected to the same endpoint (sadstat[.]com) – likely a stager download for C2, which was then initiated via connections on port 443 later that same day.

A week on from the intial C2 connection, a SQL server was detected engaging in network scanning as the attacker sought to move laterally in search of sensitive and valuable data. Over the course of two weeks, Darktrace witnessed unusual internal RDP connections using administrative credentials, before data was uploaded to multiple cloud storage endpoints as well as an SSH server. PsExec was used to deploy the ransomware, resulting in file encryption.

The evasive nature of modern ransomware

REvil started with an inherent advantage in that they were armed with the credentials of a highly privileged IT admin. Nevertheless, they still made several attempts to evade traditional, signature-based tools, such as ‘Living off the Land’ – using common tools such PsExec, WMI, RDP to blend into to legitimate activity.

They leveraged frequently-used cloud storage solutions like Dropbox and pCloud for data transfer, and they conducted SSH on port 443, blending in with SSL connections on the same port. They used a newly-registered domain for C2 communication, meaning Open Source Intelligence Tools (OSINT) were blind to the threat.

Finally, the malware itself was evasive in that it made use of code obfuscation and encryption, and had no need for a system library or API imports. This is the basis for most modern ransomware attacks, and the reality is signature-based tools cannot keep up. Darktrace’s AI not only detected the anomalous activity associated with every stage of the attack, but generated fleshed-out summaries of each stage of the attack with Cyber AI Analyst.

Cyber AI Analyst: Real-time incident reporting

Between September 21 and October 12, Cyber AI Analyst created 15 incidents, investigating dozens of point detections and creating a coherent attack narrative.

Figure 3: Cyber AI Incident log of the first compromised DC. This incident tab details the connections to sadstat[.]com

Figure 4: The DC establishes C2 to the first GHOSTnet GmbH IP

Figure 5: This incident tab highlights the file encryption of files on network shares

Figure 6: Darktrace surfaces the IT admin account takeover

Figure 7: Example of a client type device involved in extensive administrative RDP and SMB activity, as well as data uploads to Dropbox (this upload to Dropbox occurs few seconds before file encryption begins)

REvil vs AI

This Sodinokibi ransomware attack slipped under the radar of a range of traditional tools deployed by the retail organization. However, despite the threat dwelling in the retail organization’s digital environment for over a month, and REvil using local tools to blend in to regular traffic, from Darktrace’s perspective these actions were noisy in comparison to the organization’s normal ‘pattern of life’, setting off a series of alerts and investigations.

Darktrace’s Cyber AI Analyst was able to autonomously investigate nearly every attack phase of the ransomware. The technology works around the clock, without requiring training or time off, and can often reduce hours or days of incident response into just minutes, reducing time to triage by up to 92% and augmenting the capabilities of the human security team.

Thanks to Darktrace analyst Joel Lee for his insights on the above threat find.

Learn more about Cyber AI Analyst

Darktrace model detections:

  • Anomalous Connection / Active Remote Desktop Tunnel
  • Anomalous Connection / Data Sent To New External Device
  • Anomalous Connection / Data Sent to Rare Domain
  • Anomalous Connection / High Volume of New or Uncommon Service Control
  • Anomalous Connection / SMB Enumeration
  • Anomalous Connection / Uncommon 1 GiB Outbound
  • Anomalous Connection / Unusual Admin RDP Session
  • Anomalous Connection / Unusual Admin SMB Session
  • Anomalous File / Internal / Additional Extension Appended to SMB File
  • Anomalous Server Activity / Anomalous External Activity from Critical Network Device
  • Compliance / SMB Drive Write
  • Compliance / Possible Tor Usage
  • Compromise / Ransomware / Ransom or Offensive Words Written to SMB
  • Compromise / Ransomware / Suspicious SMB Activity
  • Device / ICMP Address Scan
  • Device / Multiple Lateral Movement Model Breaches
  • Device / Network Scan
  • Device / New or Uncommon WMI Activity
  • Device / New or Unusual Remote Command Execution
  • Device / RDP Scan
  • Device / Suspicious Network Scan Activity
  • Unusual Activity / Enhanced Unusual External Data Transfer
  • Unusual Activity / Unusual Internal Connections
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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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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