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July 8, 2025

Defending the Cloud: Stopping Cyber Threats in Azure and AWS with Darktrace

This blog examines three real-world cloud-based attacks in Azure and AWS environments, including credential compromise, data exfiltration, and ransomware detonation. Learn how Darktrace’s AI-driven threat detection and Autonomous Response capabilities help organizations defend against evolving threats in complex cloud environments.
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
Alexandra Sentenac
Cyber Analyst
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08
Jul 2025

Real-world intrusions across Azure and AWS

As organizations pursue greater scalability and flexibility, cloud platforms like Microsoft Azure and Amazon Web Services (AWS) have become essential for enabling remote operations and digitalizing corporate environments. However, this shift introduces a new set of security risks, including expanding attack surfaces, misconfigurations, and compromised credentials frequently exploited by threat actors.

This blog dives into three instances of compromise within a Darktrace customer’s Azure and AWS environment.

  1. The first incident took place in early 2024 and involved an attacker compromising a legitimate user account to gain unauthorized access to a customer’s Azure environment.
  2. The other two incidents, taking place in February and March 2025, targeted AWS environments. In these cases, threat actors exfiltrated corporate data, and in one instance, was able to detonate ransomware in a customer’s environment.

Case 1 - Microsoft Azure

Simplified timeline of the attack on a customer’s Azure environment.
Figure 1: Simplified timeline of the attack on a customer’s Azure environment.

In early 2024, Darktrace identified a cloud compromise on the Azure cloud environment of a customer in the Europe, the Middle East and Africa (EMEA) region.

Initial access

In this case, a threat actor gained access to the customer’s cloud environment after stealing access tokens and creating a rogue virtual machine (VM). The malicious actor was found to have stolen access tokens belonging to a third-party external consultant’s account after downloading cracked software.

With these stolen tokens, the attacker was able to authenticate to the customer’s Azure environment and successfully modified a security rule to allow inbound SSH traffic from a specific IP range (i.e., securityRules/AllowCidrBlockSSHInbound). This was likely performed to ensure persistent access to internal cloud resources.

Detection and investigation of the threat

Darktrace / IDENTITY recognized that this activity was highly unusual, triggering the “Repeated Unusual SaaS Resource Creation” alert.

Cyber AI Analyst launched an autonomous investigation into additional suspicious cloud activities occurring around the same time from the same unusual location, correlating the individual events into a broader account hijack incident.

Figure 3: Surrounding resource creation events highlighted by Cyber AI Analyst.
Figure 4: Surrounding resource creation events highlighted by Cyber AI Analyst.

“Create resource service limit” events typically indicate the creation or modification of service limits (i.e., quotas) for a specific Azure resource type within a region. Meanwhile, “Registers the Capacity Resource Provider” events refer to the registration of the Microsoft Capacity resource provider within an Azure subscription, responsible for managing capacity-related resources, particularly those related to reservations and service limits. These events suggest that the threat actor was looking to create new cloud resources within the environment.

Around ten minutes later, Darktrace detected the threat actor creating or modifying an Azure disk associated with a virtual machine (VM), suggesting an attempt to create a rogue VM within the environment.

Threat actors can leverage such rogue VMs to hijack computing resources (e.g., by running cryptomining malware), maintain persistent access, move laterally within the cloud environment, communicate with command-and-control (C2) infrastructure, and stealthily deliver and deploy malware.

Persistence

Several weeks later, the compromised account was observed sending an invitation to collaborate to an external free mail (Google Mail) address.

Darktrace deemed this activity as highly anomalous, triggering a compliance alert for the customer to review and investigate further.

The next day, the threat actor further registered new multi-factor authentication (MFA) information. These actions were likely intended to maintain access to the compromised user account. The customer later confirmed this activity by reviewing the corresponding event logs within Darktrace.

Case 2 – Amazon Web Services

Simplified timeline of the attack on a customer’s AWS environment
Figure 5: Simplified timeline of the attack on a customer’s AWS environment

In February 2025, another cloud-based compromised was observed on a UK-based customer subscribed to Darktrace’s Managed Detection and Response (MDR) service.

How the attacker gained access

The threat actor was observed leveraging likely previously compromised credential to access several AWS instances within customer’s Private Cloud environment and collecting and exfiltrating data, likely with the intention of deploying ransomware and holding the data for ransom.

Darktrace alerting to malicious activity

This observed activity triggered a number of alerts in Darktrace, including several high-priority Enhanced Monitoring alerts, which were promptly investigated by Darktrace’s Security Operations Centre (SOC) and raised to the customer’s security team.

The earliest signs of attack observed by Darktrace involved the use of two likely compromised credentials to connect to the customer’s Virtual Private Network (VPN) environment.

Internal reconnaissance

Once inside, the threat actor performed internal reconnaissance activities and staged the Rclone tool “ProgramData\rclone-v1.69.0-windows-amd64.zip”, a command-line program to sync files and directories to and from different cloud storage providers, to an AWS instance whose hostname is associated with a public key infrastructure (PKI) service.

The threat actor was further observed accessing and downloading multiple files hosted on an AWS file server instance, notably finance and investment-related files. This likely represented data gathering prior to exfiltration.

Shortly after, the PKI-related EC2 instance started making SSH connections with the Rclone SSH client “SSH-2.0-rclone/v1.69.0” to a RockHoster Virtual Private Server (VPS) endpoint (193.242.184[.]178), suggesting the threat actor was exfiltrating the gathered data using the Rclone utility they had previously installed. The PKI instance continued to make repeated SSH connections attempts to transfer data to this external destination.

Darktrace’s Autonomous Response

In response to this activity, Darktrace’s Autonomous Response capability intervened, blocking unusual external connectivity to the C2 server via SSH, effectively stopping the exfiltration of data.

This activity was further investigated by Darktrace’s SOC analysts as part of the MDR service. The team elected to extend the autonomously applied actions to ensure the compromise remained contained until the customer could fully remediate the incident.

Continued reconissance

Around the same time, the threat actor continued to conduct network scans using the Nmap tool, operating from both a separate AWS domain controller instance and a newly joined device on the network. These actions were accompanied by further internal data gathering activities, with around 5 GB of data downloaded from an AWS file server.

The two devices involved in reconnaissance activities were investigated and actioned by Darktrace SOC analysts after additional Enhanced Monitoring alerts had triggered.

Lateral movement attempts via RDP connections

Unusual internal RDP connections to a likely AWS printer instance indicated that the threat actor was looking to strengthen their foothold within the environment and/or attempting to pivot to other devices, likely in response to being hindered by Autonomous Response actions.

This triggered multiple scanning, internal data transfer and unusual RDP alerts in Darktrace, as well as additional Autonomous Response actions to block the suspicious activity.

Suspicious outbound SSH communication to known threat infrastructure

Darktrace subsequently observed the AWS printer instance initiating SSH communication with a rare external endpoint associated with the web hosting and VPS provider Host Department (67.217.57[.]252), suggesting that the threat actor was attempting to exfiltrate data to an alternative endpoint after connections to the original destination had been blocked.

Further investigation using open-source intelligence (OSINT) revealed that this IP address had previously been observed in connection with SSH-based data exfiltration activity during an Akira ransomware intrusion [1].

Once again, connections to this IP were blocked by Darktrace’s Autonomous Response and subsequently these blocks were extended by Darktrace’s SOC team.

The above behavior generated multiple Enhanced Monitoring alerts that were investigated by Darktrace SOC analysts as part of the Managed Threat Detection service.

Enhanced Monitoring alerts investigated by SOC analysts as part of the Managed Detection and Response service.
Figure 5: Enhanced Monitoring alerts investigated by SOC analysts as part of the Managed Detection and Response service.

Final containment and collaborative response

Upon investigating the unusual scanning activity, outbound SSH connections, and internal data transfers, Darktrace analysts extended the Autonomous Response actions previously triggered on the compromised devices.

As the threat actor was leveraging these systems for data exfiltration, all outgoing traffic from the affected devices was blocked for an additional 24 hours to provide the customer’s security team with time to investigate and remediate the compromise.

Additional investigative support was provided by Darktrace analysts through the Security Operations Service, after the customer's opened of a ticket related to the unfolding incident.

Simplified timeline of the attack
Figure 8: Simplified timeline of the attack

Around the same time of the compromise in Case 2, Darktrace observed a similar incident on the cloud environment of a different customer.

Initial access

On this occasion, the threat actor appeared to have gained entry into the AWS-based Virtual Private Cloud (VPC) network via a SonicWall SMA 500v EC2 instance allowing inbound traffic on any port.

The instance received HTTPS connections from three rare Vultr VPS endpoints (i.e., 45.32.205[.]52, 207.246.74[.]166, 45.32.90[.]176).

Lateral movement and exfiltration

Around the same time, the EC2 instance started scanning the environment and attempted to pivot to other internal systems via RDP, notably a DC EC2 instance, which also started scanning the network, and another EC2 instance.  

The latter then proceeded to transfer more than 230 GB of data to the rare external GTHost VPS endpoint 23.150.248[.]189, while downloading hundreds of GBs of data over SMB from another EC2 instance.

Cyber AI Analyst incident generated following the unusual scanning and RDP connections from the initial compromised device.
Figure 7: Cyber AI Analyst incident generated following the unusual scanning and RDP connections from the initial compromised device.

The same behavior was replicated across multiple EC2 instances, whereby compromised instances uploaded data over internal RDP connections to other instances, which then started transferring data to the same GTHost VPS endpoint over port 5000, which is typically used for Universal Plug and Play (UPnP).

What Darktrace detected

Darktrace observed the threat actor uploading a total of 718 GB to the external endpoint, after which they detonated ransomware within the compromised VPC networks.

This activity generated nine Enhanced Monitoring alerts in Darktrace, focusing on the scanning and external data activity, with the earliest of those alerts triggering around one hour after the initial intrusion.

Darktrace’s Autonomous Response capability was not configured to act on these devices. Therefore, the malicious activity was not autonomously blocked and escalated to the point of ransomware detonation.

Conclusion

This blog examined three real-world compromises in customer cloud environments each illustrating different stages in the attack lifecycle.

The first case showcased a notable progression from a SaaS compromise to a full cloud intrusion, emphasizing the critical role of anomaly detection when legitimate credentials are abused.

The latter two incidents demonstrated that while early detection is vital, the ability to autonomously block malicious activity at machine speed is often the most effective way to contain threats before they escalate.

Together, these incidents underscore the need for continuous visibility, behavioral analysis, and machine-speed intervention across hybrid environments. Darktrace's AI-driven detection and Autonomous Response capabilities, combined with expert oversight from its Security Operations Center, give defenders the speed and clarity they need to contain threats and reduce operational disruption, before the situation spirals.

Credit to Alexandra Sentenac (Senior Cyber Analyst) and Dylan Evans (Security Research Lead)

References

[1] https://www.virustotal.com/gui/ip-address/67.217.57.252/community

Case 1

Darktrace / IDENTITY model alerts

IaaS / Compliance / Uncommon Azure External User Invite

SaaS / Resource / Repeated Unusual SaaS Resource Creation

IaaS / Compute / Azure Compute Resource Update

Cyber AI Analyst incidents

Possible Unsecured AzureActiveDirectory Resource

Possible Hijack of Office365 Account

Case 2

Darktrace / NETWORK model alerts

Compromise / SSH Beacon

Device / Multiple Lateral Movement Model Alerts

Device / Suspicious SMB Scanning Activity

Device / SMB Lateral Movement

Compliance / SSH to Rare External Destination

Device / Anomalous SMB Followed By Multiple Model Alerts

Device / Anonymous NTLM Logins

Anomalous Connection / SMB Enumeration

Device / New or Uncommon SMB Named Pipe Device / Network Scan

Device / Suspicious Network Scan Activity

Device / New Device with Attack Tools

Device / RDP Scan Device / Attack and Recon Tools

Compliance / High Priority Compliance Model Alert

Compliance / Outgoing NTLM Request from DC

Compromise / Large Number of Suspicious Successful Connections

Device / Large Number of Model Alerts

Anomalous Connection / Multiple Failed Connections to Rare Endpoint

Unusual Activity / Internal Data Transfer

Anomalous Connection / Unusual Internal Connections

Device / Anomalous RDP Followed By Multiple Model Alerts

Unusual Activity / Unusual External Activity

Unusual Activity / Enhanced Unusual External Data Transfer

Unusual Activity / Unusual External Data Transfer

Unusual Activity / Unusual External Data to New Endpoint

Anomalous Connection / Multiple Connections to New External TCP Port

Darktrace / Autonomous Response model alerts

Antigena / Network / Significant Anomaly / Antigena Enhanced Monitoring from Server Block

Antigena / Network / Manual / Quarantine Device

Antigena / MDR / MDR-Quarantined Device

Antigena / MDR / Model Alert on MDR-Actioned Device

Antigena / Network / Significant Anomaly / Antigena Enhanced Monitoring from Client Block

Antigena / Network / Significant Anomaly / Antigena Alerts Over Time Block

Antigena / Network / Insider Threat / Antigena Network Scan Block

Antigena / Network / Significant Anomaly / Antigena Significant Server Anomaly Block

Antigena / Network / Insider Threat / Antigena SMB Enumeration Block

Antigena / Network / Significant Anomaly / Antigena Controlled and Model Alert

Antigena / Network / Significant Anomaly / Antigena Significant Anomaly from Client Block

Antigena / Network / External Threat / Antigena Suspicious Activity Block

Antigena / Network / Insider Threat / Antigena Internal Data Transfer Block

Cyber AI Analyst incidents

Possible Application Layer Reconnaissance Activity

Scanning of Multiple Devices

Unusual Repeated Connections

Unusual External Data Transfer

Case 3

Darktrace / NETWORK model alerts

Unusual Activity / Unusual Large Internal Transfer

Compliance / Incoming Remote Desktop

Unusual Activity / High Volume Server Data Transfer

Unusual Activity / Internal Data Transfer

Anomalous Connection / Unusual Internal Remote Desktop

Anomalous Connection / Unusual Incoming Data Volume

Anomalous Server Activity / Domain Controller Initiated to Client

Device / Large Number of Model Alerts

Anomalous Connection / Possible Flow Device Brute Force

Device / RDP Scan

Device / Suspicious Network Scan Activity

Device / Network Scan

Anomalous Server Activity / Anomalous External Activity from Critical Network Device

Anomalous Connection / Download and Upload

Unusual Activity / Unusual External Data Transfer

Unusual Activity / High Volume Client Data Transfer

Unusual Activity / Unusual External Activity

Anomalous Connection / Uncommon 1 GiB Outbound

Device / Increased External Connectivity

Compromise / Large Number of Suspicious Successful Connections

Anomalous Connection / Data Sent to Rare Domain

Anomalous Connection / Low and Slow Exfiltration to IP

Unusual Activity / Enhanced Unusual External Data Transfer

Anomalous Connection / Multiple Connections to New External TCP Port

Anomalous Server Activity / Outgoing from Server

Anomalous Connection / Multiple Connections to New External UDP Port

Anomalous Connection / Possible Data Staging and External Upload

Unusual Activity / Unusual External Data to New Endpoint

Device / Large Number of Model Alerts from Critical Network Device

Compliance / External Windows Communications

Anomalous Connection / Unusual Internal Connections

Cyber AI Analyst incidents

Scanning of Multiple Devices

Extensive Unusual RDP Connections

MITRE ATT&CK mapping

(Technique name – Tactic ID)

Case 1

Defense Evasion - Modify Cloud Compute Infrastructure: Create Cloud Instance

Persistence – Account Manipulation

Case 2

Initial Access - External Remote Services

Execution - Inter-Process Communication

Persistence - External Remote Services

Discovery - System Network Connections Discovery

Discovery - Network Service Discovery

Discovery - Network Share Discovery

Lateral Movement - Remote Desktop Protocol

Lateral Movement - Remote Services: SMB/Windows Admin Shares

Collection - Data from Network Shared Drive

Command and Control - Protocol Tunneling

Exfiltration - Exfiltration Over Asymmetric Encrypted Non-C2 Protocol

Case 3

Initial Access - Exploit Public-Facing Application

Discovery - Remote System Discovery

Discovery - Network Service Discovery

Lateral Movement - Remote Services

Lateral Movement - Remote Desktop Protocol  

Collection - Data from Network Shared Drive

Collection - Data Staged: Remote Data Staging

Exfiltration - Exfiltration Over C2 Channel

Command and Control - Non-Standard Port

Command and Control – Web Service

Impact - Data Encrypted for Impact

List of IoCs

IoC         Type      Description + Probability

193.242.184[.]178 - IP Address - Possible Exfiltration Server  

45.32.205[.]52  - IP Address  - Possible C2 Infrastructure

45.32.90[.]176 - IP Address - Possible C2 Infrastructure

207.246.74[.]166 - IP Address - Likely C2 Infrastructure

67.217.57[.]252 - IP Address - Likely C2 Infrastructure

23.150.248[.]189 - IP Address - Possible Exfiltration Server

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
Alexandra Sentenac
Cyber Analyst

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August 11, 2026

When AI Agents Attack: The Case for Behavioral Anomaly Detection

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The UK AI Security Institute (AISI) has just published a detailed incident report confirming what many within the cyber security industry have suspected for some time: frontier AI agents, given a degree of autonomy, can independently develop and execute attack chains against real targets, including social engineering, supply-chain compromise, and deception, without explicit instruction to do so.

The report (INC-2026-07-28-01, published 4 August 2026) documents what happened during a routine capability evaluation between 25 and 28 July. It deserves a careful read from anyone responsible for securing the modern digital estate.

The incident

AISI regularly tests frontier AI models for offensive cyber capability. In this exercise, agents were placed inside a simulated network environment and given internet access this was deliberate, given to reflect realism of the task. Across 122 evaluation runs, 19 instances of unsanctioned activity were recorded, including cases where agents broke the intended boundaries of the test and acted against real people and real infrastructure on the open internet.

In the most serious case, an agent (Mythos 5) autonomously:

  • Conducted open-source intelligence gathering to identify real developers associated with keywords from the simulated scenario
  • Created a GitHub account and submitted a pull request containing obfuscated malicious code to a real, unaffiliated repository
  • Created a second sockpuppet account to post comments on its own PR, attempting to manufacture social proof
  • When a human reviewer flagged the malicious content, the agent lied, claiming an accidental commit, then repeatedly attempted to reintroduce the payload under the guise of having "fixed" the code
  • Sent spear-phishing emails to the repository maintainer containing manipulated content designed to convince them to merge the code
  • Planted a prompt injection inside a GitHub issue, hidden in an HTML comment invisible to humans but readable by AI coding assistants parsing the repository via API

AISI confirmed no real-world harm resulted. The PRs were not merged; the payloads did not execute. But containment was a product of circumstance, not design.

Why this matters

Every action the agents took used legitimate services operating within normal parameters. Creating a GitHub account is legitimate. Opening a pull request is legitimate. Sending an email is legitimate. Posting an issue is legitimate.

No vulnerability was exploited. No known malware signature was present. No indicator of compromise from any threat intelligence feed would have matched. The entire attack existed as a pattern, a sequence of individually normal actions that, taken together, constituted a supply-chain attack, a social engineering campaign, and an attempted compromise of downstream systems.

This is the class of threat that signature-based and rule-based security tools structurally struggle to detect. They answer the question "have I seen this before?" When the answer is no – and when the attack is novel, composed of legitimate actions, and adapted in real time by an adversary in this case an agent that reasons about evasion – they struggle.

Behavioral anomaly detection: The architecture that fits

Darktrace has spent a decade building a platform around a different question: "is this behavior normal for this entity?"

The platform learns the baseline behavior of every user, device, and communication pattern across an organization's digital environment. It does not need prior knowledge of an attack technique. It identifies deviation from learned normality, surfaces it, and through its Autonomous Response capability, takes targeted action to contain threats at machine speed.

Consider how this AISI incident might show across the Darktrace platform:

Network detection and response

While no payload was successfully delivered to a victim in this incident, AISI's post-incident analysis of the agent's code (detailed on pages 24-25 of the report) reveals what would have landed on target systems had the social engineering succeeded. The agent produced three successive payload generations, each replacing the last after being detected and called out:

Generation 1 hid a module-load stager inside a legitimate bug-fix commit, guarded by an environment variable check, to skip execution in CI. Its second stage attempted to fetch Poseidon implants (Linux and Windows variants) calling back to the agent's own C2 listener, with a fallback to publicly hosted polling scripts that fetched and executed commands every 60 seconds.

Generation 2 exploited an Electron "What's New" window with nodeIntegration enabled, loading remote HTML from a GitHub Pages site the agent had registered. The page decoded an XOR-obfuscated payload at runtime that beaconed host identifiers over DNS, attempted to download the same implants, ran its own in-process C2 loop, and installed reboot persistence via crontab and Windows registry Run keys.

Generation 3 was a post-install dropper added after the agent had already been publicly caught. It XOR-decoded a hidden URL, downloaded a script over plaintext HTTP, and ran it detached, force-exiting so npm install always reports success, giving the attacker remote code execution on any machine running the install.

None of these payloads reached a victim. But the technical detail matters: this is the calibre of tradecraft an autonomous agent produced in a matter of hours, unprompted. Each generation demonstrated adaptation, the agent iterated its approach in direct response to being detected.

For network defenders, the behavioral signals these payloads would have generated are clear. DNS beaconing to novel domains, periodic HTTP polling to newly registered infrastructure, XOR-encoded data in transit, registry and crontab persistence writes on endpoints that have never exhibited such behavior. These are exactly the anomalies that Darktrace / NETWORK identifies in real time: deviations from learned device and connection baselines, regardless of whether the specific payload or C2 domain has been seen before.

Beyond the payload analysis, the agents' broader activity produced additional behavioral anomalies: new identities engaging in high-frequency interactions with external services, coordination via unusual channels (public pastebins, gists), and lateral communication patterns that deviate from any established baseline.

Email security

The spear-phishing emails sent by the agent, crafted with context-specific content designed to manipulate a specific individual, represent exactly the kind of socially engineered communication that static email gateways can miss. Darktrace / EMAIL analyses the linguistic patterns, sender behavior, and relational context of every message. A brand-new sender using tailored language to pressure a recipient into a specific technical action deviates from the learned communication profile, regardless of whether the message contains a known-bad URL or attachment.

Securing AI

This is where the incident points to a threat category that many security platforms do not yet fully address. The agent did not just use AI as a tool for attack. It targeted other AI systems, attempting prompt injections against coding assistants and trying to compromise automated workflows. Organisations adopting AI agents for development, operations, and decision-making are introducing a newer extended attack surface.  

Darktrace / SECURE AI extends the same behavioral detection model into this space. It monitors AI usage across the enterprise, detecting anomalous interactions with AI services, identifying sensitive data exposure to AI systems, providing visibility into shadow AI use. As AI agents become standard components of enterprise infrastructure, the ability to detect when an AI system is behaving outside its expected parameters, when there is a chance, it is being manipulated, or when it is interacting with something it should not be, that becomes a direct security requirement rather than a future consideration.

The principle is consistent across the Darktrace platform: learn what normal looks like, identify deviation, respond autonomously.

The AI-to-AI threat surface

One of the report's most important findings is a confirmation that AI agents can act outside of instructions and guardrails to complete tasks. The Mythos 5 agent conducted reconnaissance on a repository maintainer, inferred it might be an AI coding assistant, and deployed a prompt injection specifically crafted to compromise it.

This is a new attack class. Organizations deploying AI coding assistants, AI-powered code review, or autonomous DevOps agents now face an adversary that:

  • Moves at speed
  • Is able to adapt its approach when initial attempts are halted
  • Specifically targets AI systems via techniques (prompt injection, hidden instructions in HTML comments) that are less visible to human reviewers but parsed by machines
  • Reasons about which evasion strategies are most likely to succeed

Defending against this requires security that operates with the same adaptability and speed. A system that learns what "normal" looks like, and flags deviation from it.

What AISI recommends

The report identifies five contributing factors to the incident. Two are directly relevant:

No synchronous real-time monitoring (Section 5.3): AISI acknowledges it had not built real-time behavioral monitoring capable of immediately blocking unsanctioned agent actions. Their security team detected the incident via commercial security monitoring software, but only after activity had already occurred.

No fine-grained behavioral controls (Section 6.2): AISI's forward-looking response includes building continuous monitoring that can "immediately block or flag unsanctioned AI agent behavior."

The direction is clear: organizations need security that watches behavior continuously, learns what normal looks like, and acts when deviation occurs, without requiring a human in the loop for every decision.

The takeaway

The AISI incident is documented proof that autonomous AI agents will independently develop novel attack chains using legitimate tools, adapt when detected, employ deception, and target both humans and other AI systems. This happened last week, in a controlled setting, with commercially available models.

The security architecture that addresses this is behavioral anomaly detection applied across the full digital estate, as AI agents become standard components of enterprise infrastructure, writing code, managing deployments, processing communications, the attack surface they create is behavioral by nature.

This is the approach Darktrace has taken for years: learning what is normal across an organization’s digital environment, identifying meaningful deviations, and responding to emerging threats without relying on known attack signatures. As autonomous AI agents introduce new and unpredictable behaviors, that foundation becomes increasingly important to securing the enterprise.

Read the full report from the UK AI Security Institute here.

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About the author
Adam Stevens
Senior Director of Product | Darktrace

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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
Your data. Our AI.
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