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October 13, 2023

Protecting Brazilian Organizations from Malware

Discover how Darktrace DETECT thwarted a banking trojan targeting Brazilian organizations, preventing data theft and informing the customer.
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
Roberto Romeu
Senior SOC Analyst
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13
Oct 2023

Nationally Targeted Cyber Attacks

As the digital world becomes more and more interconnected, the threat of cyber-attacks transcends borders and presents a significant concern to security teams worldwide. Yet despite this, some malicious actors have shown a tendency to focus their attacks on specific countries. By employing highly tailored tactics, techniques, and procedures (TTPs) to target users and organizations from one nation, rather than launching more widespread campaigns, threat actors are able to maximize the efficiency and efficacy of their attacks.

What is Guildma and how does it work?

One example can be seen in the remote access trojan (RAT) and information stealer, Guildma. Guildma, also known by the demonic moniker, Astaroth, first appeared in the wild in 2017 and is a Latin America-based banking trojan known to primarily target organizations in Brazil, although has more recently been observed in North America and Europe too [1].

By concentrating their efforts on Brazil, Guildma is able to launch attacks with a high degree of specificity, focussing their language on Brazilian norms, referencing Brazilian institutions, and tailoring their social engineering accordingly. Moreover, considering that Brazilian customers likely represent a relatively small portion of security vendors’ clientele, there may be a limited pool of available indicators of compromise (IoCs). This limitation could significantly impact the efficacy of traditional security measures that rely on signature-based detection methods in identifying emerging threats.

Darktrace vs. Guildma

In June 2023, Darktrace observed a Guildma compromise on the network of a Brazilian customer in the manufacturing sector. The anomaly-based detection capabilities of Darktrace DETECT™ allowed it to identify suspicious activity surrounding the compromise, agnostic of any IoCs or specific signatures of a threat actor. Following the successful detection of the malware, the Darktrace Security Operations Center (SOC) carried out a thorough investigation into the compromise and brought it to the attention of the customer’s security team, allowing them to quickly react and prevent any further escalation.

This early detection by Darktrace effectively shut down Guildma operations on the network before any sensitive data could be gathered and stolen by malicious actors.

Attack Overview

In the case of the Guildma RAT detected by Darktrace, the affected system was a desktop device, ostensibly used by one employee. The desktop was first observed on the customer’s network in April 2023; however, it is possible that the initial compromise took place before Darktrace had visibility over the network. Guildma compromises typically start with phishing campaigns, indicating that the initial intrusion in this case likely occurred beyond the scope of Darktrace’s monitoring [2].

Early indicators

On June 23, 2023, Darktrace DETECT observed the first instance of unusual activity being performed by the affected desktop device, namely regular HTTP POST requests to a suspicious domain, indicative of command-and-control (C2) beaconing activity. The domain used an unusual Top-Level Domain (TLD), with a plausibly meaningful (in Portuguese) second-level domain and a seemingly random 11-character third-level domain, “dn00x1o0f0h.puxaofolesanfoneiro[.]quest”.

Throughout the course of this attack, Darktrace observed additional connections like this, representing something of a signature of the attack. The suspicious domains were typically registered within six months of observation, featured an uncommon TLD, and included a seemingly randomized third-level domain of 6-11 characters, followed by a plausibly legitimate second-level domain with a minimum of 15 characters. The connections to these unusual endpoints all followed a similar two-hour beaconing period, suggesting that Guildma may rotate its C2 infrastructure, using the Multi-Stage Channels TTP (MITRE ID T1104) to evade restrictions by firewalls or other signature-based security tools that rely on static lists of IoCs and “known bads”.

Figure 1: Model Breach Event Log for the “Compromise / Agent Beacon (Long Period)”. The connections at two-hour intervals, including at unreasonably late hours, is consistent with beaconing for C2.

Living-off-the-land with BITS abuse

A week later, on June 30, 2023, the affected device was observed making an unusual Microsoft BITS connection. BitsAdmin is a deprecated administrative tool available on most Windows devices and can be leveraged by attackers to transfer malicious obfuscated payloads into and around an organization’s network. The domain observed during this connection, "cwiufv.pratkabelhaemelentmarta[.]shop”, follows the previously outlined domain naming convention. Multiple open-source intelligence (OSINT) sources indicated that the endpoint had links to malware and, when visited, redirected users to the Brazilian versions of WhatsApp and Zoom. This is likely a tactic employed by threat actors to ensure users are unaware of suspicious domains, and subsequent malware downloads, by redirected them to a trusted source.

Figure 2: A screenshot of the Model Breach log summary of the “Unusual BITS Activity” model breach. The breach log contains key details such as the ASN, hostname, and user agent used in the breaching connection.

Obfuscated Tooling Downloads

Within one minute of the suspicious BITS activity, Darktrace detected the device downloading a suspicious file from the aforementioned endpoint, (cwiufv.pratkabelhaemelentmarta[.]shop). The file in question appeared to be a ZIP file with the 17-digit numeric name query, namely “?37627343830628786”, with the filename “zodzXLWwaV.zip”.

However, Darktrace DETECT recognized that the file extension did not match its true file type and identified that it was, in fact, an executable (.exe) file masquerading as a ZIP file. By masquerading files downloads, threat actors are able to make their malicious files seem legitimate and benign to security teams and traditional security tools, thereby evading detection. In this case, the suspicious file in question was indeed identified as malicious by multiple OSINT sources.

Following the initial download of this masqueraded file, Darktrace also detected subsequent downloads of additional executable files from the same endpoint.  It is possible that these downloads represented Guildma actors attempting to download additional tooling, including the information-stealer widely known as Astaroth, in order to begin its data collection and exfiltration operations.

Figure 3: A screenshot of a graph produced by the Threat Visualizer of the affected device's external connections. The visual aid marks breaches with red and orange dots, creating a more intuitive explanation of observed behavior.

Darktrace SOC

The successful detection of the masqueraded file transfer triggered an Enhanced Monitoring model breach, a high-fidelity model designed to detect activity that is more likely indicative of an ongoing compromise.  

This breach was immediately escalated to the Darktrace SOC for analysis by Darktrace’s team of expert analysts who were able to complete a thorough investigation and notify the customer’s security team of the compromise in just over half an hour. The investigation carried out by Darktrace’s analysts confirmed that the activity was, indeed, malicious, and provided the customer’s security team with details around the extent of the compromise, the specific IoCs, and risks this compromise posed to their digital environment. This information empowered the customer’s security team to promptly address the issue, having a significant portion of the investigative burden reduced and resolved by the round-the-clock Darktrace analyst team.

In addition to this, Cyber AI Analyst™ launched an investigation into the ongoing compromise and was able to connect the anomalous HTTP connections to the subsequent suspicious file downloads, viewing them as one incident rather than two isolated events. AI Analyst completed its investigation in just three minutes, upon which it provided a detailed summary of events of the activity, further aiding the customer’s remediation process.

Figure 4: CyberAI Analyst summary of the suspicious activity. A prose summary of the breach activity and the meaning of the technical details is included to maintain an easily digestible stream of information.

Conclusion

While the combination of TTPs observed in this Guildma RAT compromise is not uncommon globally, the specificity to targeting organizations in Brazil allows it to be incredibly effective. By focussing on just one country, malicious actors are able to launch highly specialized attacks, adapting the language used and tailoring the social engineering effectively to achieve maximum success. Moreover, as Brazil likely represents a smaller segment of security vendors’ customers, therefore leading to a limited pool of IoCs, attackers are often able to evade traditional signature-based detections.

Darktrace DETECT’s anomaly-based approach to threat detection allows for effective detection, mitigation, and response to emerging threats, regardless of the specifics of the attack and without relying on threat intelligence or previous IoCs. Ultimately in this case, Darktrace was able to identify the suspicious activity surrounding the Guildma compromise and swiftly bring it to the attention of the customer’s security team, before any data gathering, or exfiltration activity took place.

Darktrace’s threat detection capabilities coupled with its expert analyst team and round-the-clock SOC response is a highly effective addition to an organization’s defense-in-depth, whether in Brazil or anywhere else around the world.

Credit to Roberto Romeu, Senior SOC Analyst, Taylor Breland, Analyst Team Lead, San Francisco

References

https://malpedia.caad.fkie.fraunhofer.de/details/win.astaroth

https://www.welivesecurity.com/2020/03/05/guildma-devil-drives-electric/  

Appendices

Darktrace DETECT Model Breaches

  • Compromise / Agent Beacon (Long Period)
  • Device / Unusual BITS Activity
  • Anomalous File / Anomalous Octet Stream (No User Agent)
  • Anomalous File / Masqueraded File Transfer (Enhanced Monitoring Model)
  • Anomalous File / EXE from Rare External Location
  • Anomalous File / Multiple EXE from Rare External Locations

List of IoCs

IoC Type - Description + Confidence

5q710e1srxk.broilhasoruikaliventiladorrta[.]shop - Domain - Likely C2 server

m2pkdlse8md.roilhasohlcortinartai[.]hair - Domain - Likely C2 server

cwiufv.pratkabelhaemelentmarta[.]shop - Domain - C2 server

482w5pct234.jaroilcasacorkalilc[.]ru[.]com - Domain - C2 server

dn00x1o0f0h.puxaofolesanfoneiro[.]quest - Domain - Likely C2 server

10v7mybga55.futurefrontier[.]cyou - Domain - Likely C2 server

f788gbgdclp.growthgenerator[.]cyou - Domain - Likely C2 server

6nieek.satqabelhaeiloumelsmarta[.]shop - Domain - Likely C2 server

zodzXLWwaV.zip (SHA1 Hash: 2a4062e10a5de813f5688221dbeb3f3ff33eb417 ) - File hash - Malware

IZJQCAOXQb.zip (SHA1 Hash: eaec1754a69c50eac99e774b07ef156a1ca6de06 ) - File hash - Likely malware

MITRE ATT&CK Mapping

ATT&CK Technique - Technique ID

Multi-Stage Channels - T1104

BITS Jobs - T1197

Application Layer Protocol: Web Protocols - T1071.001

Acquire Infrastructure: Web Services - T1583.006

Obtain Capabilities: Malware - T1588.001

Masquerading - T1036

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
Roberto Romeu
Senior SOC Analyst

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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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