Blog
/
/
July 10, 2019

Insights on Shamoon 3 Data-Wiping Malware

Gain insights into Shamoon 3 and learn how to protect your organization from its destructive capabilities.
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
Default blog image
10
Jul 2019

Responsible for some of the “most damaging cyber-attacks in history” since 2012, the Shamoon malware wipes compromised hard drives and overwrites key system processes, intending to render infected machines unusable. During a trial period in the network of a global company, Darktrace observed a Shamoon-powered cyber-attack on December 10, 2018 — when several Middle Eastern firms were impacted by a new variant of the malware.

While there has been detailed reporting on the malware files and wiper modules that these latest Shamoon attacks employed, the complete cyber kill chain involved remains poorly understood, while the intrusions that led to the malware’s eventual “detonation” last December has not received nearly as much coverage. As a consequence, this blog post will focus on the insights that Darktrace’s cyber AI generated regarding (a) the activity of the infected devices during the “detonation” and (b) the indicators of compromise that most likely represent lateral movement activity during the weeks prior.

A high-level overview of major events leading up to the detonation on December 10th.

In the following, we will dive into that timeline more deeply in reverse chronological order, going back in time to trace the origins of the attack. Let’s begin with zero hour.

December 10: 42 devices “detonate”

A bird's-eye perspective of how Darktrace identified the alerts in December 2018.

What immediately strikes the analyst’s eye is the fact that a large accumulation of alerts, indicated by the red rectangle above, took place on December 10, followed by complete network silence over the subsequent four days.

These highlighted alerts represent Darktrace’s detection of unusual network scans on remote port 445 that were conducted by 42 infected devices. These devices proceeded to scan more machines — none of which were among those already infected. Such behavior indicates that the compromised devices started scanning and were wiped independently from each other, instead of conducting worming-style activity during the detonation of the malware. The initial scanning device started its scan at 12:56 p.m. UTC, while the last scanning device started its scan at 2:07 p.m. UTC.

Not only was this activity readily apparent from the bird’s-eye perspective shown above, the detonating devices also created the highest-priority Darktrace alerts over a several day period: “Device / Network Scan” and “Device / Expanded Network Scan”:

Moreover, when investigating “Devices — Overall Score,” the detonating devices rank as the most critical assets for the time period December 8–11:

Darktrace AI generated all of the above alerts because they represented significant anomalies from the normal ‘pattern of life’ that the AI had learned for each user and device on the company’s network. Crucially, none of the alerts were the product of predefined ‘rules and signatures’ — the mechanism that conventional security tools rely on to detect cyber-threats. Rather, the AI revealed the activity because the scans were unusual for the devices given their precise nature and timing, demonstrating the necessity of the such a nuanced approach in catching elusive threats like Shamoon. Of further importance is that the company’s network consists of around 15,000 devices, meaning that a rules-based approach without the ability to prioritize the most serious threats would have drowned out the Shamoon alerts in noise.

Now that we’ve seen how cyber AI sounded the alarms during the detonation itself, let’s investigate the various indicators of suspicious lateral movement that precipitated the events of December 10. Most of this activity happened in brief bursts, each of which could have been spotted and remediated if Darktrace had been closely monitored.

November 19: Unusual Remote Powershell Usage (WinRM)

One such burst of unusual activity occurred on November 19, when Darktrace detected 14 devices — desktops and servers alike — that all successfully used the WinRM protocol. None of these devices had previously used WinRM, which is also unusual for the organization’s environment as a whole. Conversely, Remote PowerShell is quite often abused in intrusions during lateral movement. The devices involved did not classify as traditional administrative devices, making their use of WinRM even more suspicious.

Note the clustering of the WinRM activity as indicated by the timestamp on the left.

October 29–31: Scanning, Unusual PsExec & RDP Brute Forcing

Another burst of likely lateral movement occurred between October 29 and 31, when two servers were seen using PsExec in an unusual fashion. No PsExec activity had been observed in the network before or after these detections, prompting Darktrace to flag the behavior. One of the servers conducted an ICMP Ping sweep shortly before the lateral movement. Not only did both servers start using PsExec on the same day, they also used SMBv1 — which, again, was very unusual for the network.

Most legitimate administrative activity involving PsExec these days uses SMBv2. The graphic below shows several Darktrace alerts on one of the involved servers — take note of the chronology of detections at the bottom of the graphic. This clearly reads like an attacker’s diary: ICMP scan, SMBv1 usage, and unusual PsExec usage, followed by new remote service controls. This server was among the top five highest ranking devices during the analyzed time period and was easy to identify.

Following the PsExec use, the servers also started an anomalous amount of remote services via the srvsvc and svcctl pipes over SMB. They did so by starting services on remote devices with which they usually did not communicate — using SMBv1, of course. Some of the attempted communication failed due to access violation and access permission errors. Both are often seen during malicious lateral movement.

Additional context around the SMBv1 and remote srvsvc pipe activity. Note the access failure.

Thanks to Darktrace’s deep packet inspection, we can see exactly what happened on the application layer. Darktrace highlights any unusual or new activity in italics below the connections — we can easily see that the SMB activity is not only unusual because of SMBv1 being used, but also because this server had never used this type of SMB activity remotely to those particular destinations before. We can also observe remote access to the winreg pipe — likely indicating more lateral movement and persistence mechanisms being established.

The other server conducted some targeted address scanning on the network on October 29, employing typical lateral movement ports 135, 139 and 445:

Another device was observed to conduct RDP brute forcing on October 29 around the same time as the above address scan. The desktop made an unusual amount of RDP connections to another internal server.

A clear plateau in increased internal connections (blue) can be seen. Every colored dot on top represents an RDP brute force detection. This was again a clear-cut detection not drowned in other noise — these were the only RDP brute force detections for a several-month monitoring time window.

October 9–11: Unusual Credential Usage

Darktrace identifies the unusual use of credentials — for instance, if administrative credentials are used on client device on which they are not commonly used. This might indicate lateral movement where service accounts or local admin accounts have been compromised.

Darktrace identified another cluster of activity that is likely representing lateral movement, this time involving unusual credential usage. Between October 9 and 11, Darktrace identified 17 cases of new administrative credentials being used on client devices. While new administrative credentials were being used from time to time on devices as part of normal administrative activity, this strong clustering of unusual admin credential usage was outstanding. Additionally, Darktrace also identified the source of some of the credentials being used as unusual.

Conclusion

Having observed a live Shamoon infection within Darktrace, there are a few key takeaways. While the actual detonation on December 10 was automated, the intrusion that built up to it was most likely manual. The fact that all detonating devices started their malicious activity roughly at the same time — without scanning each other — indicates that the payload went off based on a trigger like a scheduled task. This is in line with other reporting on Shamoon 3.

In the weeks leading up to December 10, there were various significant signs of lateral movement that occurred in disparate bursts — indicating a ‘low-and-slow’ manual intrusion.

The adversaries used classic lateral movement techniques like RDP brute forcing, PsExec, WinRM usage, and the abuse of stolen administrative credentials.

While the organization in question had a robust security posture, an attacker only needs to exploit one vulnerability to bring down an entire system. During the lifecycle of the attack, the Darktrace Enterprise Immune System identified the threatening activity in real time and provided numerous suggested actions that could have prevented the Shamoon attack at various stages. However, human action was not taken, while the organization had yet to activate Antigena, Darktrace’s autonomous response solution, which could have acted in the security team’s stead.

Despite having limited scope during the trial period, the Enterprise Immune System was able to detect the lateral movement and detonation of the payload, which was indicative of the malicious Shamoon virus activity. A junior analyst could have easily identified the activity, as high-severity alerts were consistently generated, and the likely infected devices were at the top of the suspicious devices list.

Darktrace Antigena would have prevented the movement responsible for the spread of the virus, while also sending high-severity alerts to the security team to investigate the activity. Even the scanning on port 445 from the detonating devices would have been shut down, as it presented a significant deviation from the known behavior of all scanning devices, which would have further limited the virus’s spread, and ultimately, spared the company and its devices from attack.


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

More in this series

No items found.

Blog

/

/

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.

Continue reading
About the author
Carlo Loregian
Solutions Engineer

Blog

/

/

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.

Continue reading
About the author
The Darktrace Community
Your data. Our AI.
Elevate your network security with Darktrace AI