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December 15, 2021

Log4Shell Vulnerability Detection & Response With Darktrace

Learn how Darktrace's AI detects and responds to Log4Shell attacks. Explore real-world examples and see how Darktrace identified and mitigated cyber threats.
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
Written by
Justin Fier
SVP, Red Team Operations
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15
Dec 2021

In this blog, we’ll take a look at the Log4Shell vulnerability and provide real-world examples of how Darktrace detects and responds to attacks attempting to leverage Log4Shell in the wild.

Log4Shell is now the well-known name for CVE-2021-44228 – a severity 10 zero-day exploiting a well-known Java logging utility known as Log4j. Vulnerabilities are discovered daily, and some are more severe than others, but the fact that this open source utility is nested into nearly everything, including the Mars Ingenuity drone, makes this that much more menacing. Details and further updates about Log4Shell are still emerging at the publication date of this blog.

Typically, zero-days with the power to reach this many systems are held close to the chest and only used by nation states for high value targets or operations. This one, however, was first discovered being used against Minecraft gaming servers, shared in chat amongst gamers.

While all steps should be taken to deploy mitigations to the Log4Shell vulnerability, these can take time. As evidenced here, behavioral detection can be used to look for signs of post-exploitation activity such as scanning, coin mining, lateral movement, and other activities.

Darktrace initially detected the Log4Shell vulnerability targeting one of our customers’ Internet-facing servers, as you will see in detail in an actual anonymized threat investigation below. This was highlighted and reported using Cyber AI Analyst, unpacked here by our SOC team. Please take note that this was using pre-existing algorithms without retraining classifiers or adjusting response mechanisms in reaction to Log4Shell cyber-attacks.

How Log4Shell works

The vulnerability works by taking advantage of improper input validation by the Java Naming and Directory Interface (JNDI). A command comes in from an HTTP user-agent, encrypted HTTPS connection, or even a chat room message, and the JNDI sends that to the target system in which it gets executed. Most libraries and applications have checks and protections in place to prevent this from happening, but as seen here, they get missed at times.

Various threat actors have started to leverage the vulnerability in attacks, ranging from indiscriminate crypto-mining campaigns to targeted, more sophisticated attacks.

Real-world example 1: Log4Shell exploited on CVE ID release date

Darktrace saw this first example on December 10, the same day the CVE ID was released. We often see publicly documented vulnerabilities being weaponized within days by threat actors. This attack hit an Internet-facing device in an organization’s demilitarized zone (DMZ). Darktrace had automatically classified the server as an Internet-facing device based on its behavior.

The organization had deployed Darktrace in the on-prem network as one of many coverage areas that include cloud, email and SaaS. In this deployment, Darktrace had good visibility of the DMZ traffic. Antigena was not active in this environment, and Darktrace was in detection-mode only. Despite this fact, the client in question was able to identify and remediate this incident within hours of the initial alert. The attack was automated and had the goal of deploying a crypto-miner known as Kinsing.

In this attack, the attacker made it harder to detect the compromise by encrypting the initial command injection using HTTPS over the more common HTTP seen in the wild. Despite this method being able to bypass traditional rules and signature-based systems Darktrace was able to spot multiple unusual behaviors seconds after the initial connection.

Initial compromise details

Through peer analysis Darktrace had previously learned what this specific DMZ device and its peer group normally do in the environment. During the initial exploitation, Darktrace detected various subtle anomalies that taken together made the attack obvious.

  1. 15:45:32 Inbound HTTPS connection to DMZ server from rare Russian IP — 45.155.205[.]233;
  2. 15:45:38 DMZ server makes new outbound connection to the same rare Russian IP using two new user agents: Java user agent and curl over a port that is unusual to serve HTTP compared to previous behavior;
  3. 15:45:39 DMZ server uses an HTTP connection with another new curl user agent (‘curl/7.47.0’) to the same Russian IP. The URI contains reconnaissance information from the DMZ server.

All this activity was detected not because Darktrace had seen it before, but because it strongly deviated from the regular ‘pattern of life’ for this and similar servers in this specific organization.

This server never reached out to rare IP addresses on the Internet, using user agents it never used before, over protocol and port combinations it never uses. Every point-in-time anomaly itself may have presented slightly unusual behavior – but taken together and analyzed in the context of this particular device and environment, the detections clearly tell a bigger story of an ongoing cyber-attack.

Darktrace detected this activity with various models, for example:

  • Anomalous Connection / New User Agent to IP Without Hostname
  • Anomalous Connection / Callback on Web Facing Device

Further tooling and crypto-miner download

Less than 90 minutes after the initial compromise, the infected server started downloading malicious scripts and executables from a rare Ukrainian IP 80.71.158[.]12.

The following payloads were subsequently downloaded from the Ukrainian IP in order:

  • hXXp://80.71.158[.]12//lh.sh
  • hXXp://80.71.158[.]12/Expl[REDACTED].class
  • hXXp://80.71.158[.]12/kinsing
  • hXXp://80.71.158[.]12//libsystem.so
  • hXXp://80.71.158[.]12/Expl[REDACTED].class

Using no threat intelligence or detections based on static indicators of compromise (IoC) such as IPs, domain names or file hashes, Darktrace detected this next step in the attack in real time.

The DMZ server in question never communicated with this Ukrainian IP address in the past over these uncommon ports. It is also highly unusual for this device and its peers to download scripts or executable files from this type of external destination, in this fashion. Shortly after these downloads, the DMZ server started to conduct crypto-mining.

Darktrace detected this activity with various models, for example:

  • Anomalous File / Script from Rare External Location
  • Anomalous File / Internet Facing System File Download
  • Device / Internet Facing System with High Priority Alert

Surfacing the Log4Shell incident immediately

In addition to Darktrace detecting each individual step of this attack in real time, Darktrace Cyber AI Analyst also surfaced the overarching security incident, containing a cohesive narrative for the overall attack, as the most high-priority incident within a week’s worth of incidents and alerts in Darktrace. This means that this incident was the most obvious and immediate item highlighted to human security teams as it unfolded. Darktrace’s Cyber AI Analyst found each stage of this incident and asked the very questions you would expect of your human SOC analysts. From the natural language report generated by the Cyber AI Analyst, a summary of each stage of the incident followed by the vital data points human analysts need, is presented in an easy to digest format. Each tab signifies a different part of this incident outlining the actual steps taken during each investigative process.

The result of this is no sifting through low-level alerts, no need to triage point-in-time detections, no putting the detections into a bigger incident context, no need to write a report. All of this was automatically completed by the AI Analyst saving human teams valuable time.

The below incident report was automatically created and could be downloaded as a PDF in various languages.

Figure 1: Darktrace’s Cyber AI Analyst surfaces multiple stages of the attack and explains its investigation process

Real-world example 2: Responding to a different attack using Log4Shell

On December 12, another organization’s Internet-facing server was initially compromised via Log4Shell. While the details of the compromise are different – other IoCs are involved – Darktrace detected and surfaced the attack similarly to the first example.

Interestingly, this organization had Darktrace Antigena in autonomous mode on their server, meaning the AI can take autonomous actions to respond to ongoing cyber-attacks. These responses can be delivered via a variety of mechanisms, for instance, API interactions with firewalls, other security tools, or native responses issued by Darktrace.

In this attack the rare external IP 164.52.212[.]196 was used for command and control (C2) communication and malware delivery, using HTTP over port 88, which was highly unusual for this device, peer group and organization.

Antigena reacted in real time in this organization, based on the specific context of the attack, without any human in the loop. Antigena interacted with the organization’s firewall in this case to block any connections to or from the malicious IP address – in this case 164.52.212[.]196 – over port 88 for 2 hours with the option of escalating the block and duration if the attack appears to persist. This is seen in the illustration below:

Figure 2: Antigena’s response

Here comes the trick: thanks to Self-Learning AI, Darktrace knows exactly what the Internet-facing server usually does and does not do, down to each individual data point. Based on the various anomalies, Darktrace is certain that this represents a major cyber-attack.

Antigena now steps in and enforces the regular pattern of life for this server in the DMZ. This means the server can continue doing whatever it normally does – but all the highly anomalous actions are interrupted as they occur in real time, such as speaking to a rare external IP over port 88 serving HTTP to download executables.

Of course the human can change or lift the block at any given time. Antigena can also be configured to be in human confirmation mode, having the human in the loop at certain times during the day (e.g. office hours) or at all times, depending on an organization’s needs and requirements.

Conclusion

This blog illustrates further aspects of cyber-attacks leveraging the Log4Shell vulnerability. It also demonstrates how Darktrace detects and responds to zero-day attacks if Darktrace has visibility of the attacked entities.

While Log4Shell is dominating the IT and security news, similar vulnerabilities have surfaced in the past and will appear in the future. We’ve spoken about our approach to detecting and responding to similar vulnerabilities and surrounding cyber-attacks before, for instance:

As always, companies should aim for a defense-in-depth strategy combining preventative security controls with detection and response mechanisms, as well as strong patch management.

Thanks to Brianna Leddy (Darktrace’s Director of Analysis) for her insights on the above threat find.

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
Written by
Justin Fier
SVP, Red Team Operations

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August 5, 2026

Testing a Prompt injection Attack Against an Enterprise AI Agent

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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

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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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