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October 11, 2021

AI Uncovered Outlaw's Crypto Mining Operation

Discover how Darktrace AI technology exposed a hidden cryptocurrency mining scheme. Learn about the power of Darktrace AI in cybersecurity.
Inside the SOC
Darktrace cyber analysts are world-class experts in threat intelligence, threat hunting and incident response, and provide 24/7 SOC support to thousands of Darktrace customers around the globe. Inside the SOC is exclusively authored by these experts, providing analysis of cyber incidents and threat trends, based on real-world experience in the field.
Written by
Dr. Oakley Cox-Robinson
Senior Director of Product
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11
Oct 2021

Infamy is a paradoxical calling for cyber-criminals. While for some, bragging rights are a motivation for cyber-crime in and of themselves, notoriety is usually not a sensible goal for those hoping to avoid detection. This is what threat actors behind the prolific Emotet botnet learned earlier in 2021, for instance, when a coordinated effort was launched by eight national law enforcement agencies to take down their operation. There are, however, certain names which appear again and again in cyber security media and consistently avoid detection – names like Outlaw.

How Outlaw plans an ambush

Despite being active since 2018, very little is known about the hacking group Outlaw, which has staged numerous botnet and crypto-jacking attacks in China and internationally. The group is recognized by a variety of calling cards, be they repeated filenames or a tendency to illicitly mine Monero cryptocurrency, but its success ultimately lies in its tendency to adapt and evolve during months of dormancy between attacks.

Outlaw’s attacks are marked by constant changes and updates, which they work on in relative silence, before targeting security systems which are too-often defeated by the unfamiliarity of the threat.

In 2020, Outlaw gained attention when they updated their botnet toolset to find and eradicate other criminals’ crypto-jacking software, maximizing their own payout from infected devices. While it might come as no surprise that there’s no honor among cyber-thieves, this update also implemented more troubling changes which allowed Outlaw’s malware to evade traditional security defenses.

By switching disguises between each big robbery, and laying low with the loot, Outlaw ensures that traditional security systems which rely on historical attack data will never be ready for them, no matter how much notoriety is attached to their name. When organizations move beyond these systems’ rules-based approaches, however, adopting Self-Learning AI to protect their digital estates, they can begin to turn the tables on groups like Outlaw.

This blog explores how two pre-infected zombie devices in two very different parts of the world were activated by Outlaw’s botnet in the summer of 2021, and how Darktrace was able to detect the activity despite the devices being pre-infected.

Bounty hunting: First signs of attack

Figure 1: Timeline of the attack.

When a new device was added to the network of a Central American telecomms company in July, Darktrace detected a series of regular connections to two suspicious endpoints which it identified as beaconing behavior. The same behavior was noticed independently, but almost simultaneously, at a financial company in the APAC region, which was implementing Darktrace for the first time. Darktrace’s Self-Learning AI was able to identify the pre-infected devices by clustering similarly-behaving devices into peer groups within the local digital estates and therefore recognize that both were acting unusually based on a range of behaviors.

The first sign that the zombie devices had been activated by Outlaw was the initiation of cryptocurrency mining. Both devices, despite their geographical distance, were discovered to be connected to a single crypto-account, exemplifying the indiscriminate and exponential nature by which a botnet grows.

Outlaw has in the past restricted its activities to devices within China in what was assumed to be a show of caution, but recent activities like this one speak to a growing confidence.

The botnet recruitment process

The subsequent initiation of Internet Relay Chat (IRC) connections across port 443, a port more often associated with HTTPS activity, was perfectly characteristic of the Outlaw botnet’s earlier activity in 2020. IRC is a tool regularly used for communication between botmasters and zombie devices, but by using port 443 the attacker was attempting to blend into normal Internet traffic.

Soon after this exchange, the devices downloaded a shell script. Darktrace’s Cyber AI Analyst was able to intercept and recreate this shell script as it passed through the network, revealing its full function. Intriguingly, the script identified and excluded devices utilizing ARM architecture from the botnet. Due to its notably low battery consumption, ARM architecture is used primarily by portable mobile devices.

This selectivity is evidence that malicious crypto-mining remains Outlaw’s primary objective. By circumventing smaller devices which offer limited crypto-mining capabilities, this shell script focuses the botnet on the most high-powered, and therefore profitable, devices, such as desktop computers and servers. In this way, it reduces the Indicators of Compromise (IOCs) left behind by the wider botnet without greatly affecting the scale of its crypto-mining operation.

The two devices in question did not employ ARM architecture, and minutes later received a secondary payload containing a file named dota3[.]tar[.]gz, a sequel of sorts to the previous incarnation of the Outlaw botnet, ‘dota2’, which itself referenced a popular video game of the same name. With the arrival of this file, the devices appear to have been updated with the latest version of Outlaw’s world-spanning botnet.

This download was made possible in part by the attacker’s use of ‘Living off the Land’ tactics. By using only common Linux programs already present on the devices (‘curl’ and ‘Wget’ respectively), Outlaw had avoided having its activity flagged by traditional security systems. Wget, for instance, is ostensibly a reputable program used for retrieving content from web servers, and was never previously recorded as part of Outlaw’s TTPs (Tactics, Techniques, and Procedures).

By evolving and adapting its approach, Outlaw is continually able to outsmart and outrun rules-based security. Darktrace’s Self-Learning AI, however, kept pace, immediately identifying this Wget connection as suspicious and advising further investigation.

Figure 2: Cyber AI Analyst identifies Wget use on the morning of July 15 as suspicious and begins investigating potentially related HTTP connections made on the morning of July 14. In this way, it builds a complete picture of the attack.

The botnet unchained

In the following 36 hours, Darktrace detected over 6 million TCP and SSH connections directed to rare external IP addresses using ports often associated with SSH, such as 22, 2222, and 2022.

Exactly what the botnet was undertaking with these connections can only be speculated on. The devices may have been made part of a DDoS (Distributed Denial of Service) attack, bruteforce attempts on targeted SSH accounts, or simply have taken up the task of seeking and infecting new targets, further expanding the botnet. Darktrace recognized that neither device had made SSH connections prior to this event and, had Antigena been in active mode, would have enacted measures to stop them.

Figure 3: The behavior on the device before and after the bot was activated on July 14, 2021. The large spike in model breaches shows clear deviation from the established ‘pattern of life’.

Thankfully, the owners of both devices responded to Darktrace’s detection alerts soon enough to prevent any serious damage to their own digital estates. Had these devices remained under the influence of the botnet, the ramifications may have been far graver.

The use of SSH protocol would have allowed Outlaw to pivot into any number of activities, potentially compromising each device’s network further and causing data or monetary loss to their respective organizations.

Call the sheriff: Self-Learning AI

Rules-based security solutions operate much like the ‘wanted’ posters of the old west, looking out for the criminals who came through town last week without preparing for those riding over the hill today. When black hats and outlaws are adopting new looks and employing new techniques with every attack, a new way of responding to threats is needed.

Darktrace doesn’t need to know the name ‘Outlaw’, or the group’s history of evolving attacks, in order to stop them. With its fundamental self-learning approach, Darktrace learns its surroundings from the ground up, and identifies subtle deviations indicative of a cyber-threat. And with Autonomous Response, it will even take targeted action to neutralize the threat at machine speed, without the need for human intervention.

Thanks to Darktrace analyst Jun Qi Wong for his insights on the above threat find.

Learn more about how Cyber AI Analyst sheds light on complex attacks

Technical details

Darktrace model detections

  • Compliance / Crypto Currency Mining Activity
  • Compromise / High Priority Crypto Currency Mining [Enhanced Monitoring]
  • Anomalous Connection / New User Agent to IP Without Hostname
  • Anomalous File / Zip or Gzip from Rare External Location
  • Anomalous Connection / Application Protocol on Uncommon Port
  • Device / Increased External Connectivity
  • Unusual Activity / Unusual External Activity
  • Compromise / SSH Beacon
  • Compromise / High Frequency SSH Beacon
  • Anomalous Connection / Multiple Connections to New External TCP Port

Inside the SOC
Darktrace cyber analysts are world-class experts in threat intelligence, threat hunting and incident response, and provide 24/7 SOC support to thousands of Darktrace customers around the globe. Inside the SOC is exclusively authored by these experts, providing analysis of cyber incidents and threat trends, based on real-world experience in the field.
Written by
Dr. Oakley Cox-Robinson
Senior Director of Product

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August 5, 2026

Testing a Prompt injection Attack Against an Enterprise AI Agent

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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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