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August 27, 2024

Decrypting the Matrix: How Darktrace Uncovered a KOK08 Ransomware Attack

In May 2024, a Darktrace customer was affected by KOK08, a ransomware strain commonly used by the Matrix ransomware family. Learn more about the tactics used by this ransomware case, including double extortion, and how Darktrace is able to detect and respond to such 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
Christina Kreza
Cyber Analyst
Decrypting the Matrix: How Darktrace Uncovered a KOK08 Ransomware AttackDefault blog imageDefault blog imageDefault blog imageDefault blog imageDefault blog imageDefault blog image
27
Aug 2024

What is Matrix Ransomware?

Matrix is a ransomware family that first emerged in December 2016, mainly targeting small to medium-sized organizations across the globe in countries including the US, Belgium, Germany, Canada and the UK [1]. Although the reported number of Matrix ransomware attacks has remained relatively low in recent years, it has demonstrated ongoing development and gradual improvements to its tactics, techniques, and procedures (TTPs).

How does Matrix Ransomware work?

In earlier versions, Matrix utilized spam email campaigns, exploited Windows shortcuts, and deployed RIG exploit kits to gain initial access to target networks. However, as the threat landscape changed so did Matrix’s approach. Since 2018, Matrix has primarily shifted to brute-force attacks, targeting weak credentials on Windows machines accessible through firewalls. Attackers often exploit common and default credentials, such as “admin”, “password123”, or other unchanged default settings, particularly on systems with Remote Desktop Protocol (RDP) enabled [2] [3].

Darktrace observation of Matrix Ransomware tactics

In May 2024, Darktrace observed an instance of KOK08 ransomware, a specific strain of the Matrix ransomware family, in which some of these ongoing developments and evolutions were observed. Darktrace detected activity indicative of internal reconnaissance, lateral movement, data encryption and exfiltration, with the affected customer later confirming that credentials used for Virtual Private Network (VPN) access had been compromised and used as the initial attack vector.

Another significant tactic observed by Darktrace in this case was the exfiltration of data following encryption, a hallmark of double extortion. This method is employed by attacks to increase pressure on the targeted organization, demanding ransom not only for the decryption of files but also threatening to release the stolen data if their demands are not met. These stakes are particularly high for public sector entities, like the customer in question, as the exposure of sensitive information could result in severe reputational damage and legal consequences, making the pressure to comply even more intense.

Darktrace’s Coverage of Matrix Ransomware

Internal Reconnaissance and Lateral Movement

On May 23, 2024, Darktrace / NETWORK identified a device on the customer’s network making an unusually large number of internal connections to multiple internal devices. Darktrace recognized that this unusual behavior was indicative of internal scanning activity. The connectivity observed around the time of the incident indicated that the Nmap attack and reconnaissance tool was used, as evidenced by the presence of the URI “/nice ports, /Trinity.txt.bak”.

Although Nmap is a crucial tool for legitimate network administration and troubleshooting, it can also be exploited by malicious actors during the reconnaissance phase of the attack. This is a prime example of a ‘living off the land’ (LOTL) technique, where attackers use legitimate, pre-installed tools to carry out their objectives covertly. Despite this, Darktrace’s Self-Learning AI had been continually monitoring devices across the customers network and was able to identify this activity as a deviation from the device’s typical behavior patterns.

The ‘Device / Attack and Recon Tools’ model alert identifying the active usage of the attack and recon tool, Nmap.
Figure 1: The ‘Device / Attack and Recon Tools’ model alert identifying the active usage of the attack and recon tool, Nmap.
Figure 2: Cyber AI Analyst Investigation into the ‘Scanning of Multiple Devices' incident.

Darktrace subsequently observed a significant number of connection attempts using the RDP protocol on port 3389. As RDP typically requires authentication, multiple connection attempts like this often suggest the use of incorrect username and password combinations.

Given the unusual nature of the observed activity, Darktrace’s Autonomous Response capability would typically have intervened, taking actions such as blocking affected devices from making internal connections on a specific port or restricting connections to a particular device. However, Darktrace was not configured to take autonomous action on the customer’s network, and thus their security team would have had to manually apply any mitigative measures.

Later that day, the same device was observed attempting to connect to another internal location via port 445. This included binding to the server service (srvsvc) endpoint via DCE/RPC with the “NetrShareEnum” operation, which was likely being used to list available SMB shares on a device.

Over the following two days, it became clear that the attackers had compromised additional devices and were actively engaging in lateral movement. Darktrace detected two more devices conducting network scans using Nmap, while other devices were observed making extensive WMI requests to internal systems over DCE/RPC. Darktrace recognized that this activity likely represented a coordinated effort to map the customer’s network and identity further internal devices for exploitation.

Beyond identifying the individual events of the reconnaissance and lateral movement phases of this attack’s kill chain, Darktrace’s Cyber AI Analyst was able to connect and consolidate these activities into one comprehensive incident. This not only provided the customer with an overview of the attack, but also enabled them to track the attack’s progression with clarity.

Furthermore, Cyber AI Analyst added additional incidents and affected devices to the investigation in real-time as the attack unfolded. This dynamic capability ensured that the customer was always informed of the full scope of the attack. The streamlined incident consolidation and real-time updates saved valuable time and resources, enabling quicker, more informed decision-making during a critical response window.

Cyber AI Analyst timeline showing an overview of the scanning related activity, while also connecting the suspicious lateral movement activity.
Figure 3: Cyber AI Analyst timeline showing an overview of the scanning related activity, while also connecting the suspicious lateral movement activity.

File Encryption

On May 28, 2024, another device was observed connecting to another internal location over the SMB filesharing protocol and accessing multiple files with a suspicious extension that had never previously been observed on the network. This activity was a clear sign of ransomware infection, with the ransomware altering the files by adding the “KOK08@QQ[.]COM” email address at the beginning of the filename, followed by a specific pattern of characters. The string consistently followed a pattern of 8 characters (a mix of uppercase and lowercase letters and numbers), followed by a dash, and then another 8 characters. After this, the “.KOK08” extension was appended to each file [1][4].

Cyber AI Analyst Investigation Process for the 'Possible Encryption of Files over SMB' incident.
Figure 4: Cyber AI Analyst Investigation Process for the 'Possible Encryption of Files over SMB' incident.
Cyber AI Analyst Encryption Information identifying the ransomware encryption activity,
Figure 5: Cyber AI Analyst Encryption Information identifying the ransomware encryption activity.

Data Exfiltration

Shortly after the encryption event, another internal device on the network was observed uploading an unusually large amount of data to the rare external endpoint 38.91.107[.]81 via SSH. The timing of this activity strongly suggests that this exfiltration was part of a double extortion strategy. In this scenario, the attacker not only encrypts the target’s files but also threatens to leak the stolen data unless a ransom is paid, leveraging both the need for decryption and the fear of data exposure to maximize pressure on the victim.

The full impact of this double extortion tactic became evident around two months later when a ransomware group claimed possession of the stolen data and threatened to release it publicly. This development suggested that the initial Matrix ransomware attackers may have sold the exfiltrated data to a different group, which was now attempting to monetize it further, highlighting the ongoing risk and potential for exploitation long after the initial attack.

External data being transferred from one of the involved internal devices during and after the encryption took place.
Figure 6: External data being transferred from one of the involved internal devices during and after the encryption took place.

Unfortunately, because Darktrace’s Autonomous Response capability was not enabled at the time, the ransomware attack was able to escalate to the point of data encryption and exfiltration. However, Darktrace’s Security Operations Center (SOC) was still able to support the customer through the Security Operations Support service. This allowed the customer to engage directly with Darktrace’s expert analysts, who provided essential guidance for triaging and investigating the incident. The support from Darktrace’s SOC team not only ensured the customer had the necessary information to remediate the attack but also expedited the entire process, allowing their security team to quickly address the issue without diverting significant resources to the investigation.

Conclusion

In this Matrix ransomware attack on a Darktrace customer in the public sector, malicious actors demonstrated an elevated level of sophistication by leveraging compromised VPN credentials to gain initial access to the target network. Once inside, they exploited trusted tools like Nmap for network scanning and lateral movement to infiltrate deeper into the customer’s environment. The culmination of their efforts was the encryption of files, followed by data exfiltration via SSH, suggesting that Matrix actors were employing double extortion tactics where the attackers not only demanded a ransom for decryption but also threatened to leak sensitive information.

Despite the absence of Darktrace’s Autonomous Response at the time, its anomaly-based approach played a crucial role in detecting the subtle anomalies in device behavior across the network that signalled the compromise, even when malicious activity was disguised as legitimate.  By analyzing these deviations, Darktrace’s Cyber AI Analyst was able to identify and correlate the various stages of the Matrix ransomware attack, constructing a detailed timeline. This enabled the customer to fully understand the extent of the compromise and equipped them with the insights needed to effectively remediate the attack.

Credit to Christina Kreza (Cyber Analyst) and Ryan Traill (Threat Content Lead)

Appendices

Darktrace Model Detections

·       Device / Network Scan

·       Device / Attack and Recon Tools

·       Device / Possible SMB/NTLM Brute Force

·       Device / Suspicious SMB Scanning Activity

·       Device / New or Uncommon SMB Named Pipe

·       Device / Initial Breach Chain Compromise

·       Device / Multiple Lateral Movement Model Breaches

·       Device / Large Number of Model Breaches from Critical Network Device

·       Device / Multiple C2 Model Breaches

·       Device / Lateral Movement and C2 Activity

·       Anomalous Connection / SMB Enumeration

·       Anomalous Connection / New or Uncommon Service Control

·       Anomalous Connection / Multiple Connections to New External TCP Port

·       Anomalous Connection / Data Sent to Rare Domain

·       Anomalous Connection / Uncommon 1 GiB Outbound

·       Unusual Activity / Enhanced Unusual External Data Transfer

·       Unusual Activity / SMB Access Failures

·       Compromise / Ransomware / Suspicious SMB Activity

·       Compromise / Suspicious SSL Activity

List of Indicators of Compromise (IoCs)

·       .KOK08 -  File extension - Extension to encrypted files

·       [KOK08@QQ[.]COM] – Filename pattern – Prefix of the encrypted files

·       38.91.107[.]81 – IP address – Possible exfiltration endpoint

MITRE ATT&CK Mapping

·       Command and control – Application Layer Protocol – T1071

·       Command and control – Web Protocols – T1071.001

·       Credential Access – Password Guessing – T1110.001

·       Discovery – Network Service Scanning – T1046

·       Discovery – File and Directory Discovery – T1083

·       Discovery – Network Share Discovery – T1135

·       Discovery – Remote System Discovery – T1018

·       Exfiltration – Exfiltration Over C2 Channer – T1041

·       Initial Access – Drive-by Compromise – T1189

·       Initial Access – Hardware Additions – T1200

·       Lateral Movement – SMB/Windows Admin Shares – T1021.002

·       Reconnaissance – Scanning IP Blocks – T1595.001

References

[1] https://unit42.paloaltonetworks.com/matrix-ransomware/

[2] https://www.sophos.com/en-us/medialibrary/PDFs/technical-papers/sophoslabs-matrix-report.pdf

[3] https://cyberenso.jp/en/types-of-ransomware/matrix-ransomware/

[4] https://www.pcrisk.com/removal-guides/10728-matrix-ransomware

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
Christina Kreza
Cyber Analyst

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May 5, 2026

When Trust Becomes the Attack Surface: Supply-Chain Attacks in an Era of Automation and Implicit Trust

Software supply chain attacksDefault blog imageDefault blog image

Software supply-chain attacks in 2026

Software supply-chain attacks now represent the primary threat shaping the 2026 security landscape. Rather than relying on exploits at the perimeter, attackers are targeting the connective tissue of modern engineering environments: package managers, CI/CD automation, developer systems, and even the security tools organizations inherently trust.

These incidents are not isolated cases of poisoned code. They reflect a structural shift toward abusing trusted automation and identity at ecosystem scale, where compromise propagates through systems designed for speed, not scrutiny. Ephemeral build runners, regardless of provider, represent high‑trust, low‑visibility execution zones.

The Axios compromise and the cascading Trivy campaign illustrate how quickly this abuse can move once attacker activity enters build and delivery workflows. This blog provides an overview of the latest supply chain and security tool incidents with Darktrace telemetry and defensive actions to improve organizations defensive cyber posture.

1. Why the Axios Compromise Scaled

On 31 March 2026, attackers hijacked the npm account of Axios’s lead maintainer, publishing malicious versions 1.14.1 and 0.30.4 that silently pulled in a malicious dependency, plain‑crypto‑[email protected]. Axios is a popular HTTP client for node.js and  processes 100 million weekly downloads and appears in around 80% of cloud and application environments, making this a high‑leverage breach [1].

The attack chain was simple yet effective:

  • A compromised maintainer account enabled legitimate‑looking malicious releases.
  • The poisoned dependency executed Remote Access Trojans (RATs) across Linux, macOS and Windows systems.
  • The malware beaconed to a remote command-and-control (C2) server every 60 seconds in a loop, awaiting further instructions.
  • The installer self‑cleaned by deleting malicious artifacts.

All of this matters because a single maintainer compromise was enough to project attacker access into thousands of trusted production environments without exploiting a single vulnerability.

A view from Darktrace

Multiple cases linked with the Axios compromise were identified across Darktrace’s customer base in March 2026, across both Darktrace / NETWORK and Darktrace / CLOUD deployments.

In one Darktrace / CLOUD deployment, an Azure Cloud Asset was observed establishing new external HTTP connectivity to the IP 142.11.206[.]73 on port 8000. Darktrace deemed this activity as highly anomalous for the device based on several factors, including the rarity of the endpoint across the network and the unusual combination of protocol and port for this asset. As a result, the triggering the "Anomalous Connection / Application Protocol on Uncommon Port" model was triggered in Darktrace / CLOUD. Detection was driven by environmental context rather than a known indicator at the time. Subsequent reporting later classified the destination as malicious in relation to the Axios supply‑chain compromise, reinforcing the gap that often exists between initial attacker activity and the availability of actionable intelligence. [5]

Additionally, shortly before this C2 connection, the device was observed communicating with various endpoints associated with the NPM package manager, further reinforcing the association with this attack.

Darktrace’s detection of the unusual external connection to 142.11[.]206[.]73 via port 8000.  
Figure 1: Darktrace’s detection of the unusual external connection to 142.11[.]206[.]73 via port 8000.  

Within Axios cases observed within Darktrace / NETWORK customer environments, activity generally focused on the use of newly observed cURL user agents in outbound connections to the C2 URL sfrclak[.]com/6202033, alongside the download of malicious files.

In other cases, Darktrace / NETWORK customers with Microsoft Defender for Endpoint integration received alerts flagging newly observed system executables and process launches associated with C2 communication.

A Security Integration Alert from Microsoft Defender for Endpoint associated with the Axios supply chain attack.
Figure 2: A Security Integration Alert from Microsoft Defender for Endpoint associated with the Axios supply chain attack.

2. Why Trivy bypassed security tooling trust

Between late February and March 22, 2026, the threat group TeamPCP leveraged credentials from a previous incident to insert malicious artifacts across Trivy’s distribution ecosystem, including its CI automation, release binaries, Visual Studio Code extensions, and Docker container images [2].

While public reporting has emphasized GitHub Actions, Darktrace telemetry highlights attacker execution within CI/CD runner environments, including ephemeral build runners. These execution contexts are typically granted broad trust and limited visibility, allowing malicious activity within build automation to blend into expected operational workflows, regardless of provider.

This was a coordinated multi‑phase attack:

  • 75 of 76  of trivy-action tags and all setup‑trivy tags were force‑pushed to deliver a malicious payload.
  • A malicious binary (v0.69.4) was distributed across all major distribution channels.
  • Developer machines were compromised, receiving a persistent backdoor and a self-propagating worm.
  • Secrets were exfiltrated at scale, including SSH keys, Kuberenetes tokens, database passwords, and cloud credentials across Amazon Web Service (AWS), Azure, and Google Cloud Platform (GCP).

Within Darktrace’s customer base, an AWS EC2 instance monitored by Darktrace / CLOUD  appeared to have been impacted by the Trivy attack. On March 19, the device was seen connecting to the attacker-controlled C2 server scan[.]aquasecurtiy[.]org (45.148.10[.]212), triggering the model 'Anomalous Server Activity / Outgoing from Server’ in Darktrace / CLOUD.

Despite this limited historical context, Darktrace assessed this activity as suspicious due to the rarity of the destination endpoint across the wider deployment. This resulted in the triggering of a model alert and the generation of a Cyber AI Analyst incident to further analyze and correlate the attack activity.

TeamPCP’s continued abused of GitHub Actions against security and IT tooling has also been observed more recently in Darktrace’s customer base. On April 22, an AWS asset was seen connecting to the C2 endpoint audit.checkmarx[.]cx (94.154.172[.]43). The timing of this activity suggests a potential link to a malicious Bitwarden package distributed by the threat actor, which was only available for a short timeframe on April 22. [4][3]

Figure 3: A model alert flagging unusual external connectivity from the AWS asset, as seen in Darktrace / CLOUD .

While the Trivy activity originated within build automation, the underlying failure mode mirrors later intrusions observed via management tooling. In both cases, attackers leveraged platforms designed for scale and trust to execute actions that blended into normal operational noise until downstream effects became visible.

Quest KACE: Legacy Risk, Real Impact

The Quest KACE System Management Appliance (SMA) incident reinforces that software risk is not confined to development pipelines alone. High‑trust infrastructure and management platforms are increasingly leveraged by adversaries when left unpatched or exposed to the internet.

Throughout March 2026, attackers exploited CVE 2025-32975 to authentication on outdated, internet-facing KACE appliances, gaining administrative control and pushing remote payloads into enterprise environments. Organizations still running pre-patch versions effectively handed adversaries a turnkey foothold, reaffirming a simple strategic truth: legacy management systems are now part of the supply-chain threat surface, and treating them as “low-risk utilities” is no longer defensible [3].

Within the Darktrace customer base, a potential case was identified in mid-March involving an internet-facing server that exhibited the use of a new user agent alongside unusual file downloads and unexpected external connectivity. Darktrace identified the device downloading file downloads from "216.126.225[.]156/x", "216.126.225[.]156/ct.py" and "216.126.225[.]156/n", using the user agents, "curl/8.5.0" & "Python-urllib/3.9".

The timeframe and IoCs observed point towards likely exploitation of CVE‑2025‑32975. As with earlier incidents, the activity became visible through deviations in expected system behavior rather than through advance knowledge of exploitation or attacker infrastructure. The delay between observed exploitation and its addition to the Known Exploited Vulnerabilities (KEV) catalogue underscores a recurring failure: retrospective validation cannot keep pace with adversaries operating at automation speed.

The strategic pattern: Ecosystem‑scale adversaries

The Axios and Trivy compromises are not anomalies; they are signals of a structural shift in the threat landscape. In this post-trust era, the compromise of a single maintainer, repository token, or CI/CD tag can produce large-scale blast radiuses with downstream victims numbering in the thousands. Attackers are no longer just exploiting vulnerabilities; they are exploiting infrastructure privileges, developer trust relationships, and automated build systems that the industry has generally under secured.

Supply‑chain compromise should now be treated as an assumed breach scenario, not a specialized threat class, particularly across build, integration, and management infrastructure. Organizations must operate under the assumption that compromise will occur within trusted software and automation layers, not solely at the network edge or user endpoint. Defenders should therefore expect compromise to emerge from trusted automation layers before it is labelled, validated, or widely understood.

The future of supply‑chain defense lies in continuous behavioral visibility, autonomous detection across developer and build environments, and real‑time anomaly identification.

As AI increasingly shapes software development and security operations, defenders must assume adversaries will also operate with AI in the loop. The defensive edge will come not from predicting specific compromises, but from continuously interrogating behavior across environments humans can no longer feasibly monitor at scale.

Credit to Nathaniel Jones (VP, Security & AI Strategy, FCISCO), Emma Foulger (Global Threat Research Operations Lead), Justin Torres (Senior Cyber Analyst), Tara Gould (Malware Research Lead)

Edited by Ryan Traill (Content Manager)

Appendices

References:

1)         https://www.infosecurity-magazine.com/news/hackers-hijack-axios-npm-package/

2)         https://thehackernews.com/2026/03/trivy-hack-spreads-infostealer-via.html

3)         https://thehackernews.com/2026/03/hackers-exploit-cve-2025-32975-cvss-100.html

4)         https://www.endorlabs.com/learn/shai-hulud-the-third-coming----inside-the-bitwarden-cli-2026-4-0-supply-chain-attack

5)         https://socket.dev/blog/axios-npm-package-compromised?trk=public_post_comment-text

IoCs

- 142.11.206[.]73 – IP Address – Axios supply chain C2

- sfrclak[.]com – Hostname – Axios supply chain C2

- hxxp://sfrclak[.]com:8000/6202033 - URI – Axios supply chain payload

- 45.148.10[.]212 – IP Address – Trivy supply chain C2

- scan.aquasecurtiy[.]org – Hostname - Trivy supply chain C2

- 94.154.172[.]43 – IP Address - Checkmarx/Bitwarden supply chain C2

- audit.checkmarx[.]cx – Hostname - Checkmarx/Bitwarder supply chain C2

- 216.126.225[.]156 – IP Address – Quest KACE exploitation C2

- 216.126.225[.]156/32 - URI – Possible Quest KACE exploitation payload

- 216.126.225[.]156/ct.py - URI - Possible Quest KACE exploitation payload

- 216.126.225[.]156/n - URI - Possible Quest KACE exploitation payload

- 216.126.225[.]156/x - URI - Possible Quest KACE exploitation payload

- e1ec76a0e1f48901566d53828c34b5dc – MD5 - Possible Quest KACE exploitation payload

- d3beab2e2252a13d5689e9911c2b2b2fc3a41086 – SHA1 - Possible Quest KACE exploitation payload

- ab6677fcbbb1ff4a22cc3e7355e1c36768ba30bbf5cce36f4ec7ae99f850e6c5 – SHA256 - Possible Quest KACE exploitation payload

- 83b7a106a5e810a1781e62b278909396 – MD5 - Possible Quest KACE exploitation payload

- deb4b5841eea43cb8c5777ee33ee09bf294a670d – SHA1 - Possible Quest KACE exploitation payload

- b1b2f1e36dcaa36bc587fda1ddc3cbb8e04c3df5f1e3f1341c9d2ec0b0b0ffaf – SHA256 - Possible Quest KACE exploitation payload

Darktrace Model Detections

Anomalous Connection / Application Protocol on Uncommon Port

Anomalous Server Activity / Outgoing from Server

Anomalous Connection / New User Agent to IP Without Hostname

Anomalous File / EXE from Rare External Location

Anomalous File / Script from Rare External Location

Anomalous Server Activity / New User Agent from Internet Facing System

Anomalous Server Activity / Rare External from Server

Antigena / Network / External Threat / Antigena Suspicious File Block

Antigena / Network / External Threat / Antigena Suspicious File Pattern of Life Block

Device / New User Agent

Device / Internet Facing Device with High Priority Alert

Anomalous File / New User Agent Followed By Numeric File Download

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About the author
Nathaniel Jones
VP, Security & AI Strategy, Field CISO

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May 5, 2026

How email-delivered prompt injection attacks can target enterprise AI – and why it matters

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What are email-delivered prompt injection attacks?

As organizations rapidly adopt AI assistants to improve productivity, a new class of cyber risk is emerging alongside them: email-delivered AI prompt injection. Unlike traditional attacks that target software vulnerabilities or rely on social engineering, this is the act of embedding malicious or manipulative instructions into content that an AI system will process as part of its normal workflow. Because modern AI tools are designed to ingest and reason over large volumes of data, including emails, documents, and chat histories, they can unintentionally treat hidden attacker-controlled text as legitimate input.  

At Darktrace, our analysis has shown an increase of 90% in the number of customer deployments showing signals associated with potential prompt injection attempts since we began monitoring for this type of activity in late 2025. While it is not always possible to definitively attribute each instance, internal scoring systems designed to identify characteristics consistent with prompt injection have recorded a growing number of high-confidence matches. The upward trend suggests that attackers are actively experimenting with these techniques.

Recent examples of prompt injection attacks

Two early examples of this evolving threat are HashJack and ShadowLeak, which illustrate prompt injection in practice.

HashJack is a novel prompt injection technique discovered in November 2025 that exploits AI-powered web browsers and agentic AI browser assistants. By hiding malicious instructions within the URL fragment (after the # symbol) of a legitimate, trusted website, attackers can trick AI web assistants into performing malicious actions – potentially inserting phishing links, fake contact details, or misleading guidance directly into what appears to be a trusted AI-generated output.

ShadowLeak is a prompt injection method to exfiltrate PII identified in September 2025. This was a flaw in ChatGPT (now patched by OpenAI) which worked via an agent connected to email. If attackers sent the target an email containing a hidden prompt, the agent was tricked into leaking sensitive information to the attacker with no user action or visible UI.

What’s the risk of email-delivered prompt injection attacks?

Enterprise AI assistants often have complete visibility across emails, documents, and internal platforms. This means an attacker does not need to compromise credentials or move laterally through an environment. If successful, they can influence the AI to retrieve relevant information seamlessly, without the labor of compromise and privilege escalation.

The first risk is data exfiltration. In a prompt injection scenario, malicious instructions may be embedded within an ordinary email. As in the ShadowLeak attack, when AI processes that content as part of a legitimate task, it may interpret the hidden text as an instruction. This could result in the AI disclosing sensitive data, summarizing confidential communications, or exposing internal context that would otherwise require significant effort to obtain.

The second risk is agentic workflow poisoning. As AI systems take on more active roles, prompt injection can influence how they behave over time. An attacker could embed instructions that persist across interactions, such as causing the AI to include malicious links in responses or redirect users to untrusted resources. In this way, the attacker inserts themselves into the workflow, effectively acting as a man-in-the-middle within the AI system.

Why can’t other solutions catch email-delivered prompt injection attacks?

AI prompt injection challenges many of the assumptions that traditional email security is built on. It does not fit the usual patterns of phishing, where the goal is to trick a user into clicking a link or opening an attachment.  

Most security solutions are designed to detect signals associated with user engagement: suspicious links, unusual attachments, or social engineering cues. Prompt injection avoids these indicators entirely, meaning there are fewer obvious red flags.

In this case, the intention is actually the opposite of user solicitation. The objective is simply for the email to be delivered and remain in the inbox, appearing benign and unremarkable. The malicious element is not something the recipient is expected to engage with, or even notice.

Detection is further complicated by the nature of the prompts themselves. Unlike known malware signatures or consistent phishing patterns, injected prompts can vary widely in structure and wording. This makes simple pattern-matching approaches, such as regex, unreliable. A broad rule set risks generating large numbers of false positives, while a narrow one is unlikely to capture the diversity of possible injections.

How does Darktrace catch these types of attacks?

The Darktrace approach to email security more generally is to look beyond individual indicators and assess context, which also applies here.  

For example, our prompt density score identifies clusters of prompt-like language within an email rather than just single occurrences. Instead of treating the presence of a phrase as a blocking signal, the focus is on whether there is an unusual concentration of these patterns in a way that suggests injection. Additional weighting can be applied where there are signs of obfuscation. For example, text that is hidden from the user – such as white font or font size zero – but still readable by AI systems can indicate an attempt to conceal malicious prompts.

This is combined with broader behavioral signals. The same communication context used to detect other threats remains relevant, such as whether the content is unusual for the recipient or deviates from normal patterns.

Ask your email provider about email-delivered AI prompt injection

Prompt injection targets not just employees, but the AI systems they rely on, so security approaches need to account for both.

Though there are clear indications of emerging activity, it remains to be seen how popular prompt injection will be with attackers going forward. Still, considering the potential impact of this attack type, it’s worth checking if this risk has been considered by your email security provider.

Questions to ask your email security provider

  • What safeguards are in place to prevent emails from influencing AI‑driven workflows over time?
  • How do you assess email content that’s benign for a human reader, but may carry hidden instructions intended for AI systems?
  • If an email contains no links, no attachments, and no social engineering cues, what signals would your platform use to identify malicious intent?

Visit the Darktrace / EMAIL product hub to discover how we detect and respond to advanced communication threats.  

Learn more about securing AI in your enterprise.

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About the author
Kiri Addison
Senior Director of Product
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