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July 4, 2024

A Busy Agenda: Darktrace's Detection of Qilin Ransomware as a Service Operator

This blog breaks down how Darktrace detected and analyzed Qilin, a Ransomware-as-a-Service group behind recent high-impact attacks. You’ll see how Qilin affiliates customize attacks with flexible encryption, process termination, and double-extortion techniques, as well as why its cross-platform builds in Rust and Golang make it especially evasive. Darktrace highlights three real-world cases where its AI identified likely Qilin activity across customer environments, offering insights into how behavioral detection can spot novel ransomware before disruption occurs. Readers will gain a clear view of Qilin’s toolkit, tactics, and how self-learning defense adapts to these evolving 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
Alexandra Sentenac
Cyber Analyst
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04
Jul 2024

What is Qilin Ransomware and what's its impact?

Qilin ransomware has recently dominated discussions across the cyber security landscape following its deployment in an attack on Synnovis, a UK-based medical laboratory company. The ransomware attack ultimately affected patient services at multiple National Health Service (NHS) hospitals that rely on Synnovis diagnostic and pathology services. Qilin’s origins, however, date back further to October 2022 when the group was observed seemingly posting leaked data from its first known victim on its Dedicated Leak Site (DLS) under the name Agenda[1].

The Darktrace Threat Research team investigated network artifacts related to Qilin and identified three probable cases of the ransomware across the Darktrace customer base between June 2022 and May 2024.

How Qilin Ransowmare operates as RaaS

Qilin operates as a Ransomware-as-a-Service (RaaS) that employs double extortion tactics, whereby harvested data is exfiltrated and threatened of publication on the group's DLS, which is hosted on Tor. Qilin ransomware has samples written in both the Golang and Rust programming languages, making it compilable with various operating systems, and is highly customizable.

Techniques Qilin Ransomware uses to avoid detection

When building Qilin ransomware variants to be used on their target(s), affiliates can configure settings such as:

  • Encryption modes (skip-step, percent, or speed)
  • File extensions, directories, or processes to exclude
  • Unique company IDs used as extensions on encrypted files
  • Services or processes to terminate during execution [1] [2]

Trend Micro analysts, who were the first to discover Qilin samples in August 2022, when the name "Agenda" was still used in ransom notes, found that each analyzed sample was customized for the intended victims and that "unique company IDs were used as extensions of encrypted files" [3]. This information is configurable from within the Qilin's affiliate panel's 'Targets' section, shown below.

Qilin's affiliate panel and branding

The panel's background image features the eponym Chinese legendary chimerical creature Qilin (pronounced “Ke Lin”). Despite this Chinese mythology reference, Russian language was observed being used by a Qilin operator in an underground forum post aimed at hiring affiliates and advertising their RaaS operation[2].

Qilin ransomware’s affiliate panel.
Figure 1: Qilin ransomware’s affiliate panel.

Qilin’s affiliate payment model

Qilin's RaaS program purportedly has an attractive affiliates' payment structure,

  • Affiliates earn 80% of ransom payments under USD 3 million
  • Affiliates earn 85% of ransom payments above USD 3 million [2]

Publication of stolen data and ransom payment negotiations are purportedly handled by Qilin operators. Qilin affiliates have been known to target companies located around the world and within a variety of industries, including critical sectors such as healthcare and energy.

Qilin target industries and victims

As Qilin is a RaaS operation, the choice of targets does not necessarily reflect Qilin operators' intentions, but rather that of its affiliates.  

Similarly, the tactics, techniques, procedures (TTPs) and indicators of compromise (IoC) identified by Darktrace are associated with the given affiliate deploying Qilin ransomware for their own purpose, rather than TTPs and IoCs of the Qilin group. Likewise, initial vectors of infection may vary from affiliate to affiliate.

Previous studies show that initial access to networks were gained via spear phishing emails or by leveraging exposed applications and interfaces.

Differences have been observed in terms of data exfiltration and potential C2 external endpoints, suggesting the below investigations are not all related to the same group or actor(s).

[related-resource]

Darktrace’s threat research investigation

Qlin ransomware attack breakdown

June 2022: Qilin ransomware attack exploiting VPN and SCCM servers

Key findings

  • Initial access: VPN and compromised admin account
  • Lateral movement: SCCM and VMware ESXi hosts
  • Malware observed: SystemBC, Tofsee
  • Ransom notes: Linked to Qilin naming conventions
  • Darktrace visibility: Analysts worked with customer via Ask the Expert (ATE) to expand coverage, revealing unusual scanning, rare external connections, and malware indicators tied to Qilin

Full story

Darktrace first detected an instance of Qilin ransomware back in June 2022, when an attacker was observed successfully accessing a customer’s Virtual Private Network (VPN) and compromising an administrative account, before using RDP to gain access to the customer’s Microsoft System Center Configuration Manager (SCCM) server.

From there, an attack against the customer's VMware ESXi hosts was launched. Fortunately, a reboot of their virtual machines (VM) caught the attention of the security team who further uncovered that custom profiles had been created and remote scripts executed to change root passwords on their VM hosts. Three accounts were found to have been compromised and three systems encrypted by ransomware.  

Unfortunately, Darktrace was not configured to monitor the affected subnets at the time of the attack. Despite this, the customer was able to work directly with Darktrace analysts via the Ask the Expert (ATE) service to add the subnets in question to Darktrace’s visibility, allowing it to monitor for any further unusual behavior.

Once visibility over the compromised SCCM server was established, Darktrace observed:

  • A series of unusual network scanning activities  
  • The use of Kali (a Linux distribution designed for digital forensics and penetration testing).
  • Connections to multiple rare external hosts. Many of which were using the “[.]ru” Top Level Domain (TLD).

One of the external destinations the server was attempting to connect was found to be related to SystemBC, a malware that turns infected hosts into SOCKS5 proxy bots and provides command-and-control (C2) functionality.

Additionally, the server was observed making external connections over ports 993 and 143 (typically associated with the use of the Interactive Message Access Protocol (IMAP) to multiple rare external endpoints. This was likely due to the presence of Tofsee malware on the device.

After the compromise had been contained, Darktrace identified several ransom notes following the naming convention “README-RECOVER-<extension/company_id>.txt”” on the network. This naming convention, as well as the similar “<company_id>-RECOVER-README.txt” have been referenced by open-source intelligence (OSINT) providers as associated with Qilin ransom notes[5] [6] [7].

April 2023: Manufacturing sector breach with large-scale exfiltration

Key findings

  • Initial access & movement: Extensive scanning and lateral movement via SMB, RDP, and WMI
  • Credential abuse: Use of default credentials (admin, administrator)
  • Malware/Indicators: Evidence of Cobalt Strike; suspicious WebDAV user agent and JA3 fingerprint
  • Data exfiltration: ~30 GB stolen via SSL to MEGA cloud storage
  • Darktrace analysis: Detected anomalous SMB and DCE-RPC traffic from domain controller, high-volume RDP activity, and rare external connectivity to IPs tied to command-and-control (C2). Confirmed ransom notes followed Qilin naming conventions.

Full story

The next case of Qilin ransomware observed by Darktrace took place in April 2023 on the network of a customer in the manufacturing sector in APAC. Unfortunately for the customer in this instance, Darktrace's Autonomous Response was not active on their environment and no autonomous actions were taken to contain the compromise.

Over the course of two days, Darktrace identified a wide range of malicious activity ranging from extensive initial scanning and lateral movement attempts to the writing of ransom notes that followed the aforementioned naming convention (i.e., “README-RECOVER-<extension/company_id>.txt”).

Darktrace observed two affected devices attempting to move laterally through the SMB, DCE-RPC and RDP network protocols. Default credentials (e.g., UserName, admin, administrator) were also observed in the large volumes of SMB sessions initiated by these devices. One of the target devices of these SMB connections was a domain controller, which was subsequently seen making suspicious WMI requests to multiple devices over DCE-RPC and enumerating SMB shares by binding to the ‘server service’ (srvsvc) named pipe to a high number of internal devices within a short time frame. The domain controller was further detected establishing an anomalously high number of connections to several internal devices, notably using the RDP administrative protocol via a default admin cookie.  

Repeated connections over the HTTP and SSL protocol to multiple newly observed IPs located in the 184.168.123.0/24 range were observed, indicating C2 connectivity.  WebDAV user agent and a JA3 fingerprint potentially associated with Cobalt Strike were notably observed in these connections. A few hours later, Darktrace detected additional suspicious external connections, this time to IPs associated with the MEGA cloud storage solution. Storage solutions such as MEGA are often abused by attackers to host stolen data post exfiltration. In this case, the endpoints were all rare for the network, suggesting this solution was not commonly used by legitimate users. Around 30 GB of data was exfiltrated over the SSL protocol.

Darktrace did not observe any encryption-related activity on this customer’s network, suggesting that encryption may have taken place locally or within network segments not monitored by Darktrace.

May 2024: US enterprise compromise

Key findings

  • Initial access & movement: Abuse of administrative and default credentials; lateral movement via DCE-RPC and RDP
  • Malware/Indicators: Suspicious executables (‘a157496.exe’, ‘83b87b2.exe’); abuse of RPC service LSM_API_service
  • Data exfiltration: Large amount of data exfiltrated via FTP and other channels to rare external endpoint (194.165.16[.]13)
  • C2 communications: HTTP/SSL traffic linked to Cobalt Strike, including PowerShell request for sihost64.dll
  • Darktrace analysis: Flagged unusual SMB writes, malicious file transfers, and large-scale exfiltration as highly anomalous. Confirmed widespread encryption activity targeting numerous devices and shares.

Full story

The most recent instance of Qilin observed by Darktrace took place in May 2024 and involved a customer in the US.

In this case, Darktrace initially detected affected devices using unusual administrative and default credentials. Then Darktrace observed additional Internal systems conducting abnormal activity such as:

  • Making extensive suspicious DCE-RPC requests to a range of internal locations
  • Performing network scanning
  • Making unusual internal RDP connections
  • And transferring suspicious executable files like 'a157496.exe' and '83b87b2.exe'.  

SMB writes of the file "LSM_API_service" were also observed, activity which was considered 100% unusual by Darktrace; this is an RPC service that can be abused to enumerate logged-in users and steal their tokens. Various repeated connections likely representative of C2 communications were detected via both HTTP and SSL to rare external endpoints linked in OSINT to Cobalt Strike use. During these connections, HTTP GET requests for the following URIs were observed:

/asdffHTTPS

/asdfgdf

/asdfgHTTP

/download/sihost64.dll

Notably, this included a GET request a DLL file named "sihost64.dll" from a domain controller using PowerShell.  

Over 102 GB of data may have been transferred to another previously unseen endpoint, 194.165.16[.]13, via the unencrypted File Transfer Protocol (FTP). Additionally, many non-FTP connections to the endpoint could be observed, over which more than 783 GB of data was exfiltrated. Regarding file encryption activity, a wide range of destination devices and shares were targeted.

Figure 2: Advanced Search graph displaying the total volume of data transferred over FTP to a malicious IP.

During investigations, Darktrace’s Threat Research team identified an additional customer, also based in the United States, where similar data exfiltration activity was observed in April 2024. Although no indications of ransomware encryption were detected on the network, multiple similarities were observed with the case discussed just prior. Notably, the same exfiltration IP and protocol (194.165.16[.]13 and FTP, respectively) were identified in both cases. Additional HTTP connectivity was further observed to another IP using a self-signed certificate (i.e., CN=ne[.]com,OU=key operations,O=1000,L=,ST=,C=KM) located within the same ASN (i.e., AS48721 Flyservers S.A.). Some of the URIs seen in the GET requests made to this endpoint were the same as identified in that same previous case.

Information regarding another device also making repeated connections to the same IP was described in the second event of the same Cyber AI Analyst incident. Following this C2 connectivity, network scanning was observed from a compromised domain controller, followed by additional reconnaissance and lateral movement over the DCE-RPC and SMB protocols. Darktrace again observed SMB writes of the file "LSM_API_service", as in the previous case, activity which was also considered 100% unusual for the network. These similarities suggest the same actor or affiliate may have been responsible for activity observed, even though no encryption was observed in the latter case.

Figure 3: First event of the Cyber AI Analyst investigation following the compromise activity.

According to researchers at Microsoft, some of the IoCs observed on both affected accounts are associated with Pistachio Tempest, a threat actor reportedly associated with ransomware distribution. The Microsoft threat actor naming convention uses the term "tempest" to reference criminal organizations with motivations of financial gain that are not associated with high confidence to a known non-nation state or commercial entity. While Pistachio Tempest’s TTPs have changed over time, their key elements still involve ransomware, exfiltration, and extortion. Once they've gained access to an environment, Pistachio Tempest typically utilizes additional tools to complement their use of Cobalt Strike; this includes the use of the SystemBC RAT and the SliverC2 framework, respectively. It has also been reported that Pistacho Tempest has experimented with various RaaS offerings, which recently included Qilin ransomware[4].

Conclusion

Qilin is a RaaS group that has gained notoriety recently due to high-profile attacks perpetrated by its affiliates. Despite this, the group likely includes affiliates and actors who were previously associated with other ransomware groups. These individuals bring their own modus operandi and utilize both known and novel TTPs and IoCs that differ from one attack to another.

Darktrace’s anomaly-based technology is inherently threat-agnostic, treating all RaaS variants equally regardless of the attackers’ tools and infrastructure. Deviations from a device’s ‘learned’ pattern of behavior during an attack enable Darktrace to detect and contain potentially disruptive ransomware attacks.

[related-resource]

Credit to: Alexandra Sentenac, Emma Foulger, Justin Torres, Min Kim, Signe Zaharka for their contributions.

References

[1] https://www.sentinelone.com/anthology/agenda-qilin/  

[2] https://www.group-ib.com/blog/qilin-ransomware/

[3] https://www.trendmicro.com/en_us/research/22/h/new-golang-ransomware-agenda-customizes-attacks.html

[4] https://www.microsoft.com/en-us/security/security-insider/pistachio-tempest

[5] https://www.trendmicro.com/en_us/research/22/h/new-golang-ransomware-agenda-customizes-attacks.html

[6] https://www.bleepingcomputer.com/forums/t/790240/agenda-qilin-ransomware-id-random-10-char;-recover-readmetxt-support/

[7] https://github.com/threatlabz/ransomware_notes/tree/main/qilin

Darktrace Model Detections

Internal Reconnaissance

Device / Suspicious SMB Scanning Activity

Device / Network Scan

Device / RDP Scan

Device / ICMP Address Scan

Device / Suspicious Network Scan Activity

Anomalous Connection / SMB Enumeration

Device / New or Uncommon WMI Activity

Device / Attack and Recon Tools

Lateral Movement

Device / SMB Session Brute Force (Admin)

Device / Large Number of Model Breaches from Critical Network Device

Device / Multiple Lateral Movement Model Breaches

Anomalous Connection / Unusual Admin RDP Session

Device / SMB Lateral Movement

Compliance / SMB Drive Write

Anomalous Connection / New or Uncommon Service Control

Anomalous Connection / Anomalous DRSGetNCChanges Operation

Anomalous Server Activity / Domain Controller Initiated to Client

User / New Admin Credentials on Client

C2 Communication

Anomalous Server Activity / Outgoing from Server

Anomalous Connection / Multiple Connections to New External TCP Port

Anomalous Connection / Anomalous SSL without SNI to New External

Anomalous Connection / Rare External SSL Self-Signed

Device / Increased External Connectivity

Unusual Activity / Unusual External Activity

Compromise / New or Repeated to Unusual SSL Port

Anomalous Connection / Multiple Failed Connections to Rare Endpoint

Device / Suspicious Domain

Device / Increased External Connectivity

Compromise / Sustained SSL or HTTP Increase

Compromise / Botnet C2 Behaviour

Anomalous Connection / POST to PHP on New External Host

Anomalous Connection / Multiple HTTP POSTs to Rare Hostname

Anomalous File / EXE from Rare External Location

Exfiltration

Unusual Activity / Enhanced Unusual External Data Transfer

Anomalous Connection / Data Sent to Rare Domain

Unusual Activity / Unusual External Data Transfer

Anomalous Connection / Uncommon 1 GiB Outbound

Unusual Activity / Unusual External Data to New Endpoint

Compliance / FTP / Unusual Outbound FTP

File Encryption

Compromise / Ransomware / Suspicious SMB Activity

Anomalous Connection / Sustained MIME Type Conversion

Anomalous File / Internal / Additional Extension Appended to SMB File

Compromise / Ransomware / Possible Ransom Note Write

Compromise / Ransomware / Possible Ransom Note Read

Anomalous Connection / Suspicious Read Write Ratio

IoC List

IoC – Type – Description + Confidence

93.115.25[.]139 IP C2 Server, likely associated with SystemBC

194.165.16[.]13 IP Probable Exfiltration Server

91.238.181[.]230 IP C2 Server, likely associated with Cobalt Strike

ikea0[.]com Hostname C2 Server, likely associated with Cobalt Strike

lebondogicoin[.]com Hostname C2 Server, likely associated with Cobalt Strike

184.168.123[.]220 IP Possible C2 Infrastructure

184.168.123[.]219 IP Possible C2 Infrastructure

184.168.123[.]236 IP Possible C2 Infrastructure

184.168.123[.]241 IP Possible C2 Infrastructure

184.168.123[.]247 IP Possible C2 Infrastructure

184.168.123[.]251 IP Possible C2 Infrastructure

184.168.123[.]252 IP Possible C2 Infrastructure

184.168.123[.]229 IP Possible C2 Infrastructure

184.168.123[.]246 IP Possible C2 Infrastructure

184.168.123[.]230 IP Possible C2 Infrastructure

gfs440n010.userstorage.me ga.co[.]nz Hostname Possible Exfiltration Server. Not inherently malicious; associated with MEGA file storage.

gfs440n010.userstorage.me ga.co[.]nz Hostname Possible Exfiltration Server. Not inherently malicious; associated with MEGA file storage.

Get the latest insights on emerging cyber threats

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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 6, 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. The defense must be too.

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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