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March 21, 2019

The Invisible Threat: How AI Catches the Ursnif Trojan

The cyber AI approach successfully detected the Ursnif infections even though the new variant of this malware was unknown to security vendors at the time.
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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21
Mar 2019

Over the past few months, I’ve analyzed some of the world’s stealthiest trojan attacks like Emotet, which employ deception to bypass traditional security tools that rely on rules and signatures. Guest contributor Keith Siepel also explained how cyber AI defenses managed to catch a zero-day trojan on his firm’s network for which no such rules or signatures yet exist. Indeed, with the incidence of banking trojans having increased by 239% among our customer base last year, it appears that this kind of subterfuge is the new normal.

However, one particularly sophisticated trojan, Ursnif, takes deception a step further evidence of which we are still seeing emerge. Rather than writing executable files that contain malicious code, some of its variants instead exploit vulnerabilities inherent to a user’s own applications, essentially turning the victim’s computer against them. The result of this increasingly common technique is that — once the victim has been tricked into clicking a malicious link or duped into opening an attachment via a phishing email — Ursnif begins to ‘live off the land’, blending into the victim’s environment. And by exploiting Microsoft Office and Windows features, such as document macros, PsExec, and PowerShell scripts, Ursnif can execute commands directly from the computer’s RAM.

One of the most prevalent and destructive strains of the Gozi banking malware, Ursnif was recently placed at the center of a new campaign that saw it dramatically expand its functionality. Originally created to infect hosts with spyware in order to steal sensitive banking information and user credentials, it can now also deploy advanced ransomware like GandCrab. These new functions are aided by the elusive trojan’s aforementioned file-less capabilities, which render it invisible to many security tools and allow it to hide in plain sight within legitimate, albeit corrupted applications. Shining a light on Ursnif therefore requires AI tools that can learn to spot when these applications act abnormally:

Cyber AI detects Ursnif on multiple client networks

First campaign: February 4, 2019

Darktrace detected the initial Ursnif compromise on a customer’s network when it caught several devices connecting to a highly unusual endpoint and subsequently downloading masqueraded files, causing Darktrace’s “Anomalous File / Masqueraded File Transfer” model to breach. Such files are often masqueraded as other file types not only to bypass traditional security measures but also to deceive users — for instance, with the intention of tricking a user into executing a file received in a malicious email by disguising it as a document.

As it happens, this Ursnif variant was a zero-day at the time Darktrace detected it, meaning that its files were unknown to antivirus vendors. But while the never-before-seen files bypassed the customer’s endpoint tools, Darktrace AI leveraged its understanding of the unique ‘pattern of life’ for every user and device in the customer’s network to flag these file downloads as threatening anomalies — without relying on signatures.

A sample of the masqueraded files initially downloaded:

File: xtex13.gas
File MIME type: application/x-dosexec
Size: 549.38 KB
Connection UID: C8SlueG1mT7VdcJ00

File: zyteb17.gas
File MIME type: application/x-dosexec
SHA-1 hash: 4ed60393575d6b47bd82eeb03629bdcb8876a73f
Size: 276.48 KB

File: File: adnaz2.gas
File MIME type: application/x-dosexec
Size: 380.93 KB
Connection UID: CmPOzP1AC4tzuuuW00

A sample of the endpoints detected:

kieacsangelita[.]city · 209.141.60[.]214
muikarellep[.]band · 46.29.167[.]73
cjasminedison[.]com · 185.120.58[.]13

Following the initial suspicious downloads, the compromised devices were further observed making regular connections to multiple rare destinations not previously seen on the affected network in a pattern of beaconing connectivity. In some cases, Darktrace marked these external destinations as suspicious when it recognized the hostnames they queried as algorithm-generated domains. High volumes of DNS requests for such domains is a common characteristic of malware infections, which use this tactic to maintain communication with C2 servers in spite of domain black-listing. In other cases, the endpoints were deemed suspicious because of their use of self-signed SSL certificates, which cyber-criminals often use because they do not require verification by a trusted authority.

In fact, the large volume of anomalous connections commonly triggered a number of Darktrace’s behavioral models, including:

Compromise / DGA Beacon
Anomalous Connection / Suspicious Self-Signed SSL
Compromise / High Volume of Connections with Beacon Score
Compromise / Beaconing Activity To Rare External Endpoint

Beaconing is a method of communication frequently seen when a compromised device attempts to relay information to its control infrastructure in order to receive further instructions. This behavior is characterized by persistent external connections to one or multiple endpoints, a pattern that was repeatedly observed for those devices that had previously downloaded malicious files from the endpoints later associated with the Ursnif campaign. While beaconing behavior to unusual destinations is not necessarily always indicative of infection, Darktrace AI concluded that, in combination with the suspicious file downloads, this type of activity represented a clear indication of compromise.

Figure 1: A device event log that shows the device had connected to internal mail servers shortly before downloading the malicious files.

Lateral movement and file-less capabilities

In the wake of the initial compromise, Darktrace AI also detected Ursnif’s lateral movement and file-less capabilities in real time. In the case of one infected device, an “Anomalous Connection / High Volume of New Service Control” model breach was triggered following the aforementioned suspicious activities. The device in question was flagged after making anomalous SMB connections to at least 47 other internal devices, and after accessing file shares which it had not previously connected. Subsequently, the device was observed writing to the other devices’ service control pipe – a channel used for the remote control of services. The anomalous use of these remote-control channels represent compelling examples of how Ursnif leverages its file-less capabilities to facilitate lateral movement.

Figure 2: Volume of SMB writes made to the service control pipe on internal devices by one of the infected devices, as shown on the Darktrace UI.

Although network administrators often use remote control channels for legitimate purposes, Darktrace AI considered this particular usage highly suspicious, particularly as both devices had previously breached a number of behavioral models as a result of infection.

Second campaign: March 18, 2019

A second Ursnif campaign was detected just this week. At the time of detection, no OSINT was available for the C2 servers nor the malware samples.

On a US manufacturer’s network, the initial malware download took place from: xqzuua1594[.]com/loq91/10x.php?l=mow1.jad hosted on IP 94.154.10[.]62.
Every single malware download is unique. This is indicating auto-patching or a malware factory working in the background.
Darktrace immediately identified this as another Anomalous File / Masqueraded File Transfer.

Directly after this, initial C2 was observed with the following parameters:

HTTP GET to: vwdlpknpsierra[.]email
Destination IP: 162.248.225[.]14
URI: /images/CKicJCsNNNfaJwX6CJ/0Ohp3OUfj/pI_2FszUK7ybqh33Qdwz/bOUeatCG2Qfks5DTzzO/H6SeiL8YozEYXKfornjfVt/hBgfcPVPCOf1H/2qo12IGl/L3B18ld4ZSx37TbdTUpALih/A5dl8FVHel/jMPIKnQfd/H.avi
User Agent: Mozilla/5.0 (Windows NT 10.0; WOW64; Trident/7.0; rv:11.0) like Gecko

What’s interesting here is that the C2 server provides a Sufee Admin login page:

This C2 appears to have bad operational security (OPSEC) as browsing random URIs on the server reveals some of the dashboard’s contents:

The initial C2 communication was followed by sustained TCP beaconing to ksylviauudaren[.]band on 185.180.198[.]245 over port 443 with SSL encryption using a self-signed certificate. Darktrace highlighted this C2 behavior as Compromise / Sustained TCP Beaconing Activity To Rare Endpoint and Anomalous Connection / Repeated Rare External SSL Self-Signed IP.

As of the writing of this article, the domain ksylviauudaren[.]band was still not recognized in OSINT as malicious – highlighting again Darktrace’s independence of signatures and rules to catch previously unknown threats.

Conclusion

The cyber AI approach successfully detected the Ursnif infections even though the new variant of this malware was unknown to security vendors at the time. Moreover, it even managed to catch Ursnif’s file-less capabilities for lateral movement through its modelling of expected patterns of connectivity. In terms of the wider security context, the ease with which cyber AI flagged such sophisticated malware — malware which takes action by corrupting a computer’s own applications — further demonstrates that AI anomaly detection is the only way to navigate a threat landscape increasingly populated by near-invisible trojans.

IoCs

kieacsangelita[.]city · 209.141.60[.]214
muikarellep[.]band · 46.29.167[.]73
cjasminedison[.]com · 185.120.58[.]13
xqzuua1594[.]com · 94.154.10.[6]2
vwdlpknpsierra[.]email · 162.248.225[.]14
ksylviauudaren[.]band · 185.180.198[.]245

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

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

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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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