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May 23, 2023

Darktrace’s Detection of a Hive Ransomware-as-Service

This blog investigates a new strain of ransomware, Hive, a ransomware-as-a-service. Darktrace was able to provide full visibility over the attacks.
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
Emily Megan Lim
Cyber Analyst
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23
May 2023

Update: On January 26, 2023, the Hive ransomware group was dismantled and servers associated with the sale of the ransomware were taken offline following an investigation by the FBI, German law enforcement and the National Crime Agency (NCA). The activity detailed in this blog took place in 2022, whilst the group was still active.

RaaS in Cyber Security

The threat of ransomware continues to be a constant concern for security teams across the cyber threat landscape. With the growing popularity of Ransomware-as-a-Service (RaaS), it is becoming more and more accessible for even inexperienced would-be attackers. As a result of this low barrier to entry, the volume of ransomware attacks is expected to increase significantly.

What’s more, RaaS is a highly tailorable market in which buyers can choose from varied kits and features to use in their ransomware deployments meaning attacks will rarely behave the same. To effectively detect and safeguard against these differentiations, it is crucial to implement security measures that put the emphasis on detecting anomalies and focusing on deviations in expected behavior, rather than relying on depreciated indicators of compromise (IoC) lists or playbooks that focus on attack chains unable to keep pace with the increasing speed of ransomware evolution.

In early 2022, Darktrace DETECT/Network™ identified several instances of Hive ransomware on the networks of multiple customers. Using its anomaly-based detection, Darktrace was able to successfully detect the attacks and multiple stages of the kill chain, including command and control (C2) activity, lateral movement, data exfiltration, and ultimately data encryption and the writing of ransom notes.

Hive Ransomware 

Hive ransomware is a relatively new strain that was first observed in the wild in June 2021. It is known to target a variety of industries including healthcare, energy providers, and retailers, and has reportedly attacked over 1,500 organizations, collecting more than USD 100m in ransom payments [1].

Hive is distributed via a RaaS model where its developers update and maintain the code, in return for a percentage of the eventual ransom payment, while users (or affiliates) are given the tools to carry out attacks using a highly sophisticated and complex malware they would otherwise be unable to use. Hive uses typical tactics, techniques and procedures (TTPs) associated with ransomware, though they do vary depending on the Hive affiliate carrying out the attack.

In most cases a double extortion attack is carried out, whereby data is first exfiltrated and then encrypted before a ransom demand is made. This gives attackers extra leverage as victims are at risk of having their sensitive data leaked to the public on websites such as the ‘HiveLeaks’ TOR website.

Attack Timeline

Owing to the highly customizable nature of RaaS, the tactics and methods employed by Hive actors are expected to differ on a case-by-case basis. Nonetheless in the majority of Hive ransomware incidents identified on Darktrace customer environments, Darktrace DETECT observed the following general attack stages and features. This is possibly indicative of the attacks originating from the same threat actor(s) or from a widely sold batch with a particular configuration to a variety of actors.

Figure 1: A typical timeline of a Hive attack observed by Darktrace.

Initial Access 

Although Hive actors are known to gain initial access to networks through multiple different vectors, the two primary methods reported by security researchers are the exploitation of Microsoft Exchange vulnerabilities, or the distribution of phishing emails with malicious attachments [2][3].

In the early stages of one Hive ransomware attack observed on the network of a Darktrace customer, for example, Darktrace detected a device connecting to the rare external location 23.81.246[.]84, with a PowerShell user agent via HTTP. During this connection, the device attempted to download an executable file named “file.exe”. It is possible that the file was initially accessed and delivered via a phishing email; however, as Darktrace/Email was not enabled at the time of the attack, this was outside of Darktrace’s purview. Fortunately, the connection failed the proxy authentication was thus blocked as seen in the packet capture (PCAP) in Figure 2. 

Shortly after this attempted download, the same device started to receive a high volume of incoming SSL connections from a rare external endpoint, namely 146.70.87[.]132. Darktrace logged that this endpoint was using an SSL certificate signed by Go Daddy CA, an easily obtainable and accessible SSL certificate, and that the increase in incoming SSL connections from this endpoint was unusual behavior for this device. 

It is likely that this highly anomalous activity detected by Darktrace indicates when the ransomware attack began, likely initial payload download.  

Darktrace DETECT models:

  • Anomalous Connection / Powershell to Rare External
  • Anomalous Server Activity / New Internet Facing System
Figure 2: PCAP of the HTTP connection to the rare endpoint 23.81.246[.]84 showing the failed proxy authentication.

C2 Beaconing 

Following the successful initial access, Hive actors begin to establish their C2 infrastructure on infected networks through numerous connections to C2 servers, and the download of additional stagers. 

On customer networks infected by Hive ransomware, Darktrace identified devices initiating a high volume of connections to multiple rare endpoints. This very likely represented C2 beaconing to the attacker’s infrastructure. In one particular example, further open-source intelligence (OSINT) investigation revealed that these endpoints were associated with Cobalt Strike.

Darktrace DETECT models:

  • Anomalous Connection / Multiple Connections to New External TCP
  • Anomalous Server Activity / Anomalous External Activity from Critical Network Device
  • Compromise / High Volume of Connections with Beacon Score
  • Compromise / Sustained SSL or HTTP Increase
  • Compromise / Suspicious HTTP Beacons to Dotted Quad 
  • Compromise / SSL or HTTP Beacon
  • Device / Lateral Movement and C2 Activity

Internal Reconnaissance, Lateral Movement and Privilege Escalation

After C2 infrastructure has been established, Hive actors typically begin to uninstall antivirus products in an attempt to remain undetected on the network [3]. They also perform internal reconnaissance to look for vulnerabilities and open channels and attempt to move laterally throughout the network.

Amid the C2 connections, Darktrace was able to detect network scanning activity associated with the attack when a device on one customer network was observed initiating an unusually high volume of connections to other internal devices. A critical network device was also seen writing an executable file “mimikatz.exe” via SMB which appears to be the Mimikatz attack tool commonly used for credential harvesting. 

There were also several detections of lateral movement attempts via RDP and DCE-RPC where the attackers successfully authenticated using an “Administrator” credential. In one instance, a device was also observed performing ITaskScheduler activity. This service is used to remotely control tasks running on machines and is commonly observed as part of malicious lateral movement activity. Darktrace DETECT understood that the above activity represented a deviation from the devices’ normal pattern of behavior and the following models were breached:

Darktrace DETECT models:

  • Anomalous Connection / Anomalous DRSGetNCChanges Operation
  • Anomalous Connection / New or Uncommon Service Control
  • Anomalous Connection / Unusual Admin RDP Session
  • Anomalous Connection / Unusual SMB Version 1 Connectivity
  • Compliance / SMB Drive Write
  • Device / Anomalous ITaskScheduler Activity
  • Device / Attack and Recon Tools
  • Device / Attack and Recon Tools In SMB
  • Device / EXE Files Distributed to Multiple Devices
  • Device / Suspicious Network Scan Activity
  • Device / Increase in New RPC Services
  • User / New Admin Credentials on Server

Data Exfiltration

At this stage of the attack, Hive actors have been known to carry out data exfiltration activity on infected networks using a variety of different methods. The Cybersecurity & Infrastructure Security Agency (CISA) reported that “Hive actors exfiltrate data likely using a combination of Rclone and the cloud storage service Mega[.]nz” [4]. Darktrace DETECT identified an example of this when a device on one customer network was observed making HTTP connections to endpoints related to Mega, including “w.apa.mega.co[.]nz”, with the user agent “rclone/v1.57.0” with at least 3 GiB of data being transferred externally (Figure 3). The same device was also observed transferring at least 3.6 GiB of data via SSL to the rare external IP, 158.51.85[.]157.

Figure 3: A summary of a device’s external connections to multiple endpoints and the respective amounts of data exfiltrated to Mega storage endpoints.

In another case, a device was observed uploading over 16 GiB of data to a rare external endpoint 93.115.27[.]71 over SSH. The endpoint in question was seen in earlier beaconing activity suggesting that this was likely an exfiltration event. 

However, Hive ransomware, like any other RaaS kit, can differ greatly in its techniques and features, and it is important to note that data exfiltration may not always be present in a Hive ransomware attack. In one incident detected by Darktrace, there were no signs of any data leaving the customer environment, indicating data exfiltration was not part of the Hive actor’s objectives.

Darktrace DETECT models:

  • Anomalous Connection / Data Sent to Rare Domain
  • Anomalous Connection / Lots of New Connections
  • Anomalous Connection / Multiple HTTP POSTs to Rare Hostname
  • Anomalous Connection / Suspicious Self-Signed SSL
  • Anomalous Connection / Uncommon 1 GiB Outbound
  • Device / New User Agent and New IP
  • Unusual Activity / Unusual External Data to New Endpoints
  • Unusual Activity / Unusual External Data Transfer
  • Unusual Activity / Enhanced Unusual External Data Transfer

Ransomware Deployment

In the final stage of a typical Hive ransomware attack, the ransomware payload is deployed and begins to encrypt files on infected devices. On one customer network, Darktrace detected several devices connecting to domain controllers (DC) to read a file named “xxx.exe”. Several sources have linked this file name with the Hive ransomware payload [5].

In another example, Darktrace DETECT observed multiple devices downloading the executable files “nua64.exe” and “nua64.dll” from a rare external location, 194.156.90[.]25. OSINT investigation revealed that the files are associated with Hive ransomware.

Figure 4: Security vendor analysis of the malicious file hash [6] associated with Hive ransomware. 

Shortly after the download of this executable, multiple devices were observed performing an unusual amount of file encryption, appending randomly generated strings of characters to file extensions. 

Although it has been reported that earlier versions of Hive ransomware encrypted files with a “.hive” extension [7], Darktrace observed across multiple customers that encrypted files had extensions that were partially-randomized, but consistently 20 characters long, matching the regular expression “[a-zA-Z0-9\-\_]{8}[\-\_]{1}[A-Za-z0-9\-\_]{11}”.

Figure 5: Device Event Log showing SMB reads and writes of encrypted files with a randomly generated extension of 20 characters. 

Following the successful encryption of files, Hive proceeds to drop a ransom note, named “HOW_TO_DECRYPT.txt”, into each affected directory. Typically, the ransom note will contain a link to Hive’s “sales department” and, in the event that exfiltration took place, a link to the “HiveLeaks” site, where attackers threaten to publish exfiltrated data if their demands are not met (Figure 6).  In cases of Hive ransomware detected by Darktrace, multiple devices were observed attempting to contact “HiveLeaks” TOR domains, suggesting that endpoint users had followed links provided to them in ransom notes.

Figure 6: Sample of a Hive ransom note [4].

Examples of file extensions:

  • 36C-AT9-_wm82GvBoCPC
  • 36C-AT9--y6Z1G-RFHDT
  • 36C-AT9-_x2x7FctFJ_q
  • 36C-AT9-_zK16HRC3QiL
  • 8KAIgoDP-wkQ5gnYGhrd
  • kPemi_iF_11GRoa9vb29
  • kPemi_iF_0RERIS1m7x8
  • kPemi_iF_7u7e5zp6enp
  • kPemi_iF_y4u7pB3d3f3
  • U-9Xb0-k__T0U9NJPz-_
  • U-9Xb0-k_6SkA8Njo5pa
  • zm4RoSR1_5HMd_r4a5a9 

Darktrace DETECT models:

  • Anomalous Connection / SMB Enumeration
  • Anomalous Connection / Sustained MIME Type Conversion
  • Anomalous Connection / Unusual Admin SMB Session
  • Anomalous File / Internal / Additional Extension Appended to SMB File
  • Compliance / SMB Drive Write
  • Compromise / Ransomware / Suspicious SMB Activity
  • Compromise / Ransomware / Ransom or Offensive Words Written to SMB
  • Compromise / Ransomware / Possible Ransom Note Write
  • Compromise / High Priority Tor2Web
  • Compromise / Tor2Web
  • Device / EXE Files Distributed to Multiple Devices

Conclusion

As Hive ransomware attacks are carried out by different affiliates using varying deployment kits, the tactics employed tend to vary and new IoCs are regularly identified. Furthermore, in 2022 a new variant of Hive was written using the Rust programming language. This represented a major upgrade to Hive, improving its defense evasion techniques and making it even harder to detect [8]. 

Hive is just one of many RaaS offerings currently on the market, and this market is only expected to grow in usage and diversity of presentations.  As ransomware becomes more accessible and easier to deploy it is essential for organizations to adopt efficient security measures to identify ransomware at the earliest possible stage. 

Darktrace DETECT’s Self-Learning AI understands customer networks and learns the expected patterns of behavior across an organization’s digital estate. Using its anomaly-based detection Darktrace is able to identify emerging threats through the detection of unusual or unexpected behavior, without relying on rules and signatures, or known IoCs. 

Credit to: Emily Megan Lim, Cyber Analyst, Hyeongyung Yeom, Senior Cyber Analyst & Analyst Team Lead.

Appendices

MITRE AT&CK Mapping

Reconnaissance

T1595.001 – Scanning IP Blocks

T1595.002 – Vulnerability Scanning

Resource Development

T1583.006 – Web Services

Initial Access

T1078 – Valid Accounts

T1190 – Exploit Public-Facing Application

T1200 – Hardware Additions

Execution

T1053.005 – Scheduled Task

T1059.001 – PowerShell

Persistence/Privilege Escalation

T1053.005 – Scheduled Task

T1078 – Valid Accounts

Defense Evasion

T1078 – Valid Accounts

T1207 – Rogue Domain Controller

T1550.002 – Pass the Hash

Discovery

T1018 – Remote System Discovery

T1046 – Network Service Discovery

T1083 – File and Directory Discovery

T1135 – Network Share Discovery

Lateral Movement

T1021.001 – Remote Desktop Protocol

T1021.002 – SMB/Windows Admin Shares

T1021.003 – Distributed Component Object Model

T1080 – Taint Shared Content

T1210 – Exploitation of Remote Services

T1550.002 – Pass the Hash

T1570 – Lateral Tool Transfer

Collection

T1185 – Man in the Browser

Command and Control

T1001 – Data Obfuscation

T1071 – Application Layer Protocol

T1071.001 – Web Protocols

T1090.003 – Multi-hop proxy

T1095 – Non-Application Layer Protocol

T1102.003 – One-Way Communication

T1571 – Non-Standard Port

Exfiltration

T1041 – Exfiltration Over C2 Channel

T1567.002 – Exfiltration to Cloud Storage

Impact

T1486 – Data Encrypted for Impact

T1489 – Service Stop

List of IoCs 

23.81.246[.]84 - IP Address - Likely Malicious File Download Endpoint

146.70.87[.]132 - IP Address - Possible Ransomware Endpoint

5.199.162[.]220 - IP Address - C2 Endpoint

23.227.178[.]65 - IP Address - C2 Endpoint

46.166.161[.]68 - IP Address - C2 Endpoint

46.166.161[.]93 - IP Address - C2 Endpoint

93.115.25[.]139 - IP Address - C2 Endpoint

185.150.1117[.]189 - IP Address - C2 Endpoint

192.53.123[.]202 - IP Address - C2 Endpoint

209.133.223[.]164 - IP Address - Likely C2 Endpoint

cltrixworkspace1[.]com - Domain - C2 Endpoint

vpnupdaters[.]com - Domain - C2 Endpoint

93.115.27[.]71 - IP Address - Possible Exfiltration Endpoint

158.51.85[.]157 - IP Address - Possible Exfiltration Endpoint

w.api.mega.co[.]nz - Domain - Possible Exfiltration Endpoint

*.userstorage.mega.co[.]nz - Domain - Possible Exfiltration Endpoint

741cc67d2e75b6048e96db9d9e2e78bb9a327e87 - SHA1 Hash - Hive Ransomware File

2f9da37641b204ef2645661df9f075005e2295a5 - SHA1 Hash - Likely Hive Ransomware File

hiveleakdbtnp76ulyhi52eag6c6tyc3xw7ez7iqy6wc34gd2nekazyd[.]onion - TOR Domain - Likely Hive Endpoint

References

[1] https://www.justice.gov/opa/pr/us-department-justice-disrupts-hive-ransomware-variant

[2] https://www.varonis.com/blog/hive-ransomware-analysis

[3] https://www.trendmicro.com/vinfo/us/security/news/ransomware-spotlight/ransomware-spotlight-hive 

[4]https://www.cisa.gov/news-events/cybersecurity-advisories/aa22-321a

[5] https://www.trendmicro.com/en_us/research/22/c/nokoyawa-ransomware-possibly-related-to-hive-.html

[6] https://www.virustotal.com/gui/file/60f6a63e366e6729e97949622abd9de6d7988bba66f85a4ac8a52f99d3cb4764/detection

[7] https://heimdalsecurity.com/blog/what-is-hive-ransomware/

[8] https://www.microsoft.com/en-us/security/blog/2022/07/05/hive-ransomware-gets-upgrades-in-rust/ 

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
Emily Megan Lim
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

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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
Your data. Our AI.
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