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July 27, 2026

Hiding in Plain Sight: Uncovering a Multi-Stage Ransomware Attack Through Behavioral Detection

Darktrace detected a multi-stage ransomware intrusion from its earliest stages, identifying reconnaissance, privilege escalation, lateral movement, command-and-control communications, and data exfiltration before encryption occurred. This analysis highlights how behavioral detection exposed attacker activity using legitimate tools and infrastructure, providing multiple opportunities for early intervention and containment.
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 Evzona
Cyber Analyst
ransomware attackDefault blog image
27
Jul 2026

Why ransomware has changed

Ransomware attacks have continued to increase globally, with 698 incidents reported in May 2026, representing a 48% rise compared to 472 incidents in May 2025 [1]. At the same time, the ransomware landscape is evolving. Several major ransomware groups, including LockBit [2], have been disrupted by successful joint law enforcement operations, resulting in a shift away from a small number of dominant actors towards a more fragmented and distributed ecosystem. This is increasingly composed of smaller groups who play a specialized role in the attack, such as initial access brokers, affiliates or developers.

As a result, ransomware tactics, techniques, and procedures (TTPs) are becoming more diverse and less predictable. On top of this, adversaries are leveraging native tools and legitimate penetration testing frameworks to evade detection. Anomaly-based detection is therefore critical to identify pre-ransomware activity, rather than relying on signatures associated with a handful of well-known ransomware groups.

As these attacks often unfold over several days, there is a critical window for defenders to act. In this context, behavioral-based detection plays a vital role in identifying suspicious pre-ransomware activity, and enabling early intervention before encryption or exfiltration occurs.

Inside a modern ransomware intrusion

In early 2026, Darktrace detected activity within a customer’s environment related to a multi-stage ransomware intrusion from the initial compromise. This activity does not appear to be attributable to a specific ransomware group, and no known ransomware payload was observed until the final stage.

The attack aligns with a broader industry trend in which compromised virtual private network (VPN) credentials are used as an entry point, followed by rapid internal reconnaissance and lateral movement using legitimate administrative tools. This growing preference for native tools and legitimate frameworks in cyber-attacks illustrates that it is increasingly unreliable to depend solely on traditional indicators of compromise such as known malware signatures or exploit detection.

The intrusion also involved the use of Sliver, an open-source adversary emulation framework, which is increasingly observed in real-world attacks. Originally designed for penetration testing and red teaming, Sliver has gained traction among threat actors as a stealthier alternative to more heavily signatured frameworks such as Cobalt Strike. As a legitimate framework, its use further complicates detection for security tools that rely on known malicious signatures.

Darktrace’s detection of a ransomware event in a customer’s environment

The initial compromise appears to have occurred via compromised credentials used over the VPN shortly before, or at the onset of the first indicators of suspicious activity. While it remains unclear as to how or when the threat actors gained access to these credentials, the use of initial access brokers (IABs) is a common feature of modern ransomware operations. This suggests that access to the environment may have been established several days or weeks beforehand.

The intrusion unfolded over three days, presenting multiple opportunities for early detection and intervention before ransomware deployment. The attack progressed through a compressed but structured sequence: initial access and reconnaissance were completed within hours, followed by privilege escalation and lateral movement the next day, and culminating in data exfiltration and encryption shortly thereafter. Throughout each stage, distinct behavioral anomalies emerged across the network providing clear indicators of malicious activity well before the ransomware was deployed.

While Darktrace’s Autonomous Response capability was enabled within the customer’s environment, it was not fully configured across the impacted devices, allowing the attack to progress to ransomware deployment. Had Autonomous Response been fully deployed across the affected systems, it could have taken targeted action against the earliest stages of malicious activity, potentially disrupting the intrusion before it escalated.

Figure 1: Timeline of the attack progression.

Day 1: Reconnaissance and privilege escalation

The threat actor gained access via compromised VPN credentials and initiated internal reconnaissance. Darktrace detected anomalous scanning behavior, including unusual port scanning activity and widespread network enumeration.

Specifically, Darktrace detected a high volume of east-west scanning activity across a broad range of ports, with TCP connections targeting ports 21, 80, 445, 4899 and 8080. Associated URIs suggested the use of Nmap, a widely used penetration testing tool. This highlights how attackers often leverage legitimate penetration testing tools for malicious reconnaissance, enabling them to blend into normal network activity and evade traditional signature-based detection methods.

Figure 2: Darktrace's detection of a sharp increase in anomalous internal connections, triggering multiple high-severity model alerts associated with reconnaissance activity.

Several devices were observed using administrative credentials to carry out privileged actions in a manner that was highly anomalous for the environment. This activity was accompanied by behavior consistent with SMB authentication scanning, suggesting efforts to identify and access additional systems. As the activity intensified, an increasing number of devices became involved, signalling lateral movement and further spread across the network.

Darktrace also identified privilege escalation through active directory (AD) replication abuse, specifically via the drsuapi::DRSGetNCChanges function. This technique allows an attacker with sufficient privileges to request directory replication data from a domain controller (DC), enabling them to extract credentials, including password hashes, without directly interacting with user accounts. Commonly associated with ‘DCSync’ attacks, this technique is frequently used to obtain highly privileged credentials and enable further escalation within an environment.

Figure 3: Darktrace’s detection of anomalous AD replication activity indicative of privilege escalation.

This activity was seen alongside the use of the now obsolete SMBv1, repeated NTLM authentication attempts using multiple variations of ‘Administrator’ credentials, reverse DNS scanning, and large-scale network scanning. Darktrace observed widespread use of SMBv1 across the customer’s environment, exposing a significant security weakness. As a legacy protocol with well-documented weaknesses, SMBv1 can be exploited to facilitate lateral movement, allowing the attackers to expand their access following initial compromise.

Day 3: Lateral Movement, Command & Control, and Exfiltration

Two days later, the attacker escalated privileges and expanded their foothold using living-off-the-land (LOTL) techniques such as PSExec, WMI, and RDP. Concurrently, Darktrace identified command-and-control (C2)-style communications consistent with the Sliver framework, alongside rare outbound connections to cloud infrastructure indicating potential data exfiltration. The volume and severity of observed activity increased as attack behavior intensified.

The device was observed conducting extensive lateral movement, leveraging LOTL techniques to evade detection. Activity included WMI execution (e.g. ExecQuery), DCE-RPC activity, SMB sessions and file writes, most of which were successful, as well as the deployment of PSEXESVC.exe via ADMIN$ shares and prolonged RDP sessions. Darktrace identified this behavior as highly anomalous for the environment. Such activity is commonly associated with the transfer of attacker tooling, remote command execution, and the establishment of persistent access across compromised systems.  

Figure 4: Darktrace’s detection of a spike in RPC binding events indicative of potential lateral movement.

On the same day, Darktrace detected C2-style SSL communications originating from multiple internal devices to rare external endpoints. These connections exhibited anomalous characteristics, including invalid SSL certificates and repeated connection patterns resembling beaconing. Analysis of the observed JA3 fingerprint further linked the activity to Sliver, the adversary simulation framework referenced earlier, as the hash has previously been associated with Sliver-related infrastructure [3]. The use of this framework reflects a broader trend of attackers repurposing legitimate offensive security tools for stealthy C2 communications. Connections to 137[.]220[.]59[.]55 (ASN AS20473 AS-VULTR) indicated that the communications were likely routed via a virtual private server (VPS) hosted by Vultr. Attackers often utilize VPS infrastructure from legitimate cloud providers like Vultr to obscure their true origin, blend into benign traffic, and evade IP-based detection mechanisms [4].

Figure 5: Darktrace’s Cyber AI Analyst detection of two linked unusual connections to Vultr infrastructure.

Darktrace also observed a device initiating SSL connections to safedata.s3[.]wasabisys[.]com, an endpoint associated with Wasabi cloud storage. Darktrace recognized that neither the destination nor the associated IP address had previously been observed within the environment.  More than 200 MB of data was subsequently uploaded externally to endpoints sharing the same JA3 client hash, indicating a sustained transfer session and potential data exfiltration to third-party storage. The apparent exfiltration prior to encryption is consistent with a double-extortion ransomware strategy.

Figure 6: Darktrace’s Cyber AI Analyst detection of more than 30 rare outbound connections to a Wasabi cloud storage endpoint, indicative of potential data exfiltration

Day 4: Encryption

The attack culminated in ransomware deployment, marking the transition from suspicious network activity to a business-impacting incident. Using SMB-based propagation, the threat actor encrypted thousands of files across the network, affecting multiple systems and disrupting normal operations. Throughout the encryption event, the legacy SMBv1 protocol was used extensively across multiple internal systems, resulting in a significant increase in newly encrypted files.

Figure 7: Darktrace’s detection of abnormal spikes in SMB activity and associated model alerts, indicative of ransomware encryption and propagation.

Darktrace’s Cyber AI Analyst automatically investigated and correlated the encryption activity and related events into a single incident narrative, providing the customer with real-time visibility into the attack while significantly reducing investigation time.

Figure 8: Darktrace’s Cyber AI Analyst’s investigation into the encryption activity. AI Analyst incident detailing example encryption activity in real time. Related events are automatically correlated and summarized into a clear narrative, reducing investigation time.

Defender action recommendations

What Could Have Stopped the Attack Earlier?

Although the attack ultimately resulted in ransomware deployment, there were multiple opportunities to detect, contain, and disrupt the intrusion before encryption occurred. The following actions could have significantly reduced the overall impact:

Detect and investigate indicators of reconnaissance and lateral movement

  • Unusual scanning
  • Active Directory replication anomalies consistent with DCSync activity
  • Anomalous use of native tools and processes indicative of LOTL attacks
  • Unusual use of common reconnaissance tools such as Nmap and NetScan

Contain compromised credentials and affected devices

  • Disable and reset compromised VPN credentials
  • Isolate devices performing anomalous scanning and lateral movement activity

Block suspicious external communications and data exfiltration

  • Use anomaly-based detection to detect and block repeated outbound connections to rare external infrastructure
  • Prevent data exfiltration to unauthorized cloud storage services such as Wasabi

Conclusion

The incident highlights the importance of anomaly-based detection, particularly against attacks that primarily use native or legitimate tools to evade traditional security measures. Darktrace identified suspicious activity from the first day of the compromise, providing multiple opportunities to disrupt the intrusion before it progressed to lateral movement and data exfiltration.

In this instance, detection was not the limiting factor; response time was. Prompt investigation and containment of devices exhibiting anomalous behavior could have prevented lateral movement, data exfiltration, and ultimately ransomware deployment.

As adversaries increasingly prioritize stealth over custom malware, relying instead on legitimate tools, valid credentials, and trusted infrastructure, traditional signature-based detection becomes less effective. Identifying subtle behavioral deviations early remains critical to disrupting attacks before they escalate into full-scale ransomware incidents.

Credit to Alexandra Evzona (Cyber Analyst), Priya Thapa (Senior Cyber Analyst)
Edited by Ryan Traill (Content Manager)

Appendices

References

[1] https://industrialcyber.co/ransomware/check-point-reports-ransomware-attacks-jump-48-year-over-year-despite-decline-in-overall-cyberattack-activity/

[2] https://www.europol.europa.eu/media-press/newsroom/news/law-enforcement-disrupt-worlds-biggest-ransomware-operation

[3] https://fieldeffect.com/blog/field-effect-mitigates-not-so-simplehelp-exploits-enabling-deployment-of-backdoors

[4] https://www.darktrace.com/blog/from-vps-to-phishing-how-darktrace-uncovered-saas-hijacks-through-virtual-infrastructure-abuse

Indicators of Compromise (IoCs)

IP Addresses

  • 137[.]220[.]59[.]55 – Potential C2 infrastructure (Vultr AS20473)
  • 38[.]27[.]106[.]123 – Wasabi cloud storage endpoint associated with potential data exfiltration
  • 38[.]27[.]106[.]128 – Wasabi cloud storage endpoint associated with potential data exfiltration
  • 38[.]27[.]106[.]117 – Wasabi cloud storage endpoint associated with potential data exfiltration

Domains

  • safedata[.]s3[.]wasabisys[.]com – Potential data exfiltration endpoint
  • *.wasabisys[.]com – Associated Wasabi cloud storage infrastructure

JA3 Fingerprint

  • d6828e30ab66774a91a96ae93be4ae4c – Associated with the Sliver adversary emulation framework

Files

  • Delete[.]me – File observed during reconnaissance activity, commonly associated with NetScan

Darktrace Model Coverage

·       Anomalous Connection / Active Remote Desktop Tunnel

·       Anomalous Connection / Anomalous Remote Registry Service Control

·       Anomalous Connection / Multiple Failed Windows UDP

·       Anomalous Connection / New or Uncommon Service Control

·       Anomalous Connection / New or Uncommon Service Enumeration

·       Anomalous Connection / New User Agent to IP Without Hostname

·       Anomalous Connection / SMB Enumeration

·       Anomalous Connection / Suspicious Activity On High Risk Device

·       Anomalous Connection / Suspicious Read Write Ratio

·       Anomalous Connection / Sustained MIME Type Conversion

·       Anomalous Connection / Uncommon 1 GiB Outbound

·       Anomalous Connection / Unusual Admin RDP Session

·       Anomalous Connection / Unusual Admin SMB Session

·       Anomalous Connection / Unusual SMB Version 1 Connectivity

·       Anomalous File / EXE from Rare External Location

·       Anomalous File / Internal / Additional Extension Appended to SMB File

·       Anomalous Server Activity / Outgoing from Server

·       Compromise / Beaconing Activity To External Rare

·       Compromise / Ransomware / Possible Ransom Note Read

·       Compromise / Ransomware / Ransom or Offensive Words Written to SMB

·       Compromise / Ransomware / Suspicious SMB Activity

·       Device / Anonymous NTLM Logins

·       Device / Attack and Recon Tools

·       Device / Initial Attack Chain Activity

·       Device / Large Number of Model Alerts

·       Device / Long Agent Connection to New Endpoint

·       Device / Multiple Lateral Movement Model Alerts

·       Device / Network Scan

·       Device / New or Uncommon SMB Named Pipe

·       Device / New or Unusual Remote Command Execution

·       Device / New User Agent

·       Device / Possible RPC Lateral Movement

·       Device / Possible SMB/NTLM Brute Force

·       Device / RDP Scan

·       Device / SMB Lateral Movement

·       Device / SMB Session Brute Force (Non-Admin)

·       Device / SMB Version 1 Access Failures

·       Device / Suspicious File Delete Activity

·       Device / Suspicious Network Scan Activity

·       Device / Unusual SMB Error Detected

·       Device / Unusual SMB To Critical Resource

·       Device / Unusual Winreg Operation

·       Unusual Activity / Multiple Failed Internal Connections

·       Unusual Activity / Possible RPC Recon Activity

·       Unusual Activity / Sustained Anomalous SMB Activity

·       Unusual Activity / Unusual External Data to New Endpoint

·       Unusual Activity / Unusual External Data Transfer

·       Unusual Activity / Unusual File Storage Data Transfer

·       Unusual Activity / Unusual Large Internal Transfer

·       User / New Admin Credentials on Client

·       User / NTLM Login from Unauthenticated Device

Autonomous Response Model Alerts

·       Antigena / Network / External Threat / Antigena Ransomware Block

·       Antigena / Network / External Threat / Antigena Suspicious File Block

·       Antigena / Network / Insider Threat / Antigena Active Threat SMB Write Block

·       Antigena / Network / Insider Threat / Antigena Internal Anomalous File Activity

·       Antigena / Network / Insider Threat / Antigena Large Data Volume Outbound Block

·       Antigena / Network / Insider Threat / Antigena Network Scan Block

·       Antigena / Network / Insider Threat / Antigena Unusual Privileged User Activities Block

·       Antigena / Network / Manual / Quarantine Device

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

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

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

·       Antigena / Network / Significant Anomaly / Antigena Enhanced Monitoring from Server Block 100

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

MITRE ATT&CK MAPPING

Command and control - Protocol Tunneling - T1572

Command and control – Web Protocols – T1071.001

Credential Access- Exploitation for Credential Access- T1212

Credential Access- Password Guessing- T1110

Discovery- File and Directory Discovery- T1083

Discovery- Network Service Discovery- T1046

Discovery- Network Share Discovery- T1135

Discovery- Remote System Discovery- T1018

Exfiltration- Exfiltration Over C2 Channel- T1041

Exfiltration- Exfiltration to Cloud Storage- T1567

Impact- Data Encrypted for Impact- T1486

Impact- Data Encrypted for Impact- T1486

Impact- Service Stop - T1489

Initial Access- Public-Facing Application- T1190

Lateral Movement- Exploitation of Remote Services- T1210

Lateral Movement- Remote Desktop Protocol- T1021

Lateral Movement- SMB/Windows Admin Shares- T1021

Lateral Movement- Taint Shared Content- T1080

Persistence- Modify Registry- T1112

Privilege Escalation- Exploitation for Privilege Escalation- T0890

Privilege Escalation- Valid Accounts- T1078

Reconnaissance- Scanning IP Blocks- T1595

Reconnaissance- Vulnerability Scanning- T1595

Resource Development- Malware- T1588

Stealth- File Deletion- T1070

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 Evzona
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

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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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