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May 28, 2024

Stemming the Citrix Bleed Vulnerability with Darktrace’s ActiveAI Security Platform

This blog delves into Darktrace’s investigation into the exploitation of the Citrix Bleed vulnerability on the network of a customer in late 2023. Darktrace’s Self-Learning AI ensured the customer was well equipped to track the post-compromise activity and identify affected devices.
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
Vivek Rajan
Cyber Analyst
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28
May 2024

What is Citrix Bleed?

Since August 2023, cyber threat actors have been actively exploiting one of the most significant critical vulnerabilities disclosed in recent years: Citrix Bleed. Citrix Bleed, also known as CVE-2023-4966, remained undiscovered and even unpatched for several months, resulting in a wide range of security incidents across business and government sectors [1].

How does Citrix Bleed vulnerability work?

The vulnerability, which impacts the Citrix Netscaler Gateway and Netscaler ADC products, allows for outside parties to hijack legitimate user sessions, thereby bypassing password and multifactor authentication (MFA) requirements.

When used as a means of initial network access, the vulnerability has resulted in the exfiltration of sensitive data, as in the case of Xfinity, and even the deployment of ransomware variants including Lockbit [2]. Although Citrix has released a patch to address the vulnerability, slow patching procedures and the widespread use of these products has resulted in the continuing exploitation of Citrix Bleed into 2024 [3].

How Does Darktrace Handle Citrix Bleed?

Darktrace has demonstrated its proficiency in handling the exploitation of Citrix Bleed since it was disclosed back in 2023; its anomaly-based approach allows it to efficiently identify and inhibit post-exploitation activity as soon as it surfaces.  Rather than relying upon traditional rules and signatures, Darktrace’s Self-Learning AI enables it to understand the subtle deviations in a device’s behavior that would indicate an emerging compromise, thus allowing it to detect anomalous activity related to the exploitation of Citrix Bleed.

In late 2023, Darktrace identified an instance of Citrix Bleed exploitation on a customer network. As this customer had subscribed to the Proactive Threat Notification (PTN) service, the suspicious network activity surrounding the compromise was escalated to Darktrace’s Security Operation Center (SOC) for triage and investigation by Darktrace Analysts, who then alerted the customer’s security team to the incident.

Darktrace’s Coverage

Initial Access and Beaconing of Citrix Bleed

Darktrace’s initial detection of indicators of compromise (IoCs) associated with the exploitation of Citrix Bleed actually came a few days prior to the SOC alert, with unusual external connectivity observed from a critical server. The suspicious connection in question, a SSH connection to the rare external IP 168.100.9[.]137, lasted several hours and utilized the Windows PuTTY client. Darktrace also identified an additional suspicious IP, namely 45.134.26[.]2, attempting to contact the server. Both rare endpoints had been linked with the exploitation of the Citrix Bleed vulnerability by multiple open-source intelligence (OSINT) vendors [4] [5].

Darktrace model alert highlighting an affected device making an unusual SSH connection to 168.100.9[.]137 via port 22.
Figure 1: Darktrace model alert highlighting an affected device making an unusual SSH connection to 168.100.9[.]137 via port 22.

As Darktrace is designed to identify network-level anomalies, rather than monitor edge infrastructure, the initial exploitation via the typical HTTP buffer overflow associated with this vulnerability fell outside the scope of Darktrace’s visibility. However, the aforementioned suspicious connectivity likely constituted initial access and beaconing activity following the successful exploitation of Citrix Bleed.

Command and Control (C2) and Payload Download

Around the same time, Darktrace also detected other devices on the customer’s network conducting external connectivity to various endpoints associated with remote management and IT services, including Action1, ScreenConnect and Fixme IT. Additionally, Darktrace observed devices downloading suspicious executable files, including “tniwinagent.exe”, which is associated with the tool Total Network Inventory. While this tool is typically used for auditing and inventory management purposes, it could also be leveraged by attackers for the purpose of lateral movement.

Defense Evasion

In the days surrounding this compromise, Darktrace observed multiple devices engaging in potential defense evasion tactics using the ScreenConnect and Fixme IT services. Although ScreenConnect is a legitimate remote management tool, it has also been used by threat actors to carry out C2 communication [6]. ScreenConnect itself was the subject of a separate critical vulnerability which Darktrace investigated in early 2024. Meanwhile, CISA observed that domains associated with Fixme It (“fixme[.]it”) have been used by threat actors attempting to exploit the Citrix Bleed vulnerability [7].

Reconnaissance and Lateral Movement

A few days after the detection of the initial beaconing communication, Darktrace identified several devices on the customer’s network carrying out reconnaissance and lateral movement activity. This included SMB writes of “PSEXESVC.exe”, network scanning, DCE-RPC binds of numerous internal devices to IPC$ shares and the transfer of compromise-related tools. It was at this point that Darktrace’s Self-Learning AI deemed the activity to be likely indicative of an ongoing compromise and several Enhanced Monitoring models alerted, triggering the aforementioned PTNs and investigation by Darktrace’s SOC.

Darktrace observed a server on the network initiating a wide range of connections to more than 600 internal IPs across several critical ports, suggesting port scanning, as well as conducting unexpected DCE-RPC service control (svcctl) activity on multiple internal devices, amongst them domain controllers. Additionally, several binds to server service (srvsvc) and security account manager (samr) endpoints via IPC$ shares on destination devices were detected, indicating further reconnaissance activity. The querying of these endpoints was also observed through RPC commands to enumerate services running on the device, as well as Security Account Manager (SAM) accounts.  

Darktrace also identified devices performing SMB writes of the WinRAR data compression tool, in what likely represented preparation for the compression of data prior to data exfiltration. Further SMB file writes were observed around this time including PSEXESVC.exe, which was ultimately used by attackers to conduct remote code execution, and one device was observed making widespread failed NTLM authentication attempts on the network, indicating NTLM brute-forcing. Darktrace observed several devices using administrative credentials to carry out the above activity.

In addition to the transfer of tools and executables via SMB, Darktrace also identified numerous devices deleting files through SMB around this time. In one example, an MSI file associated with the patch management and remediation service, Action1, was deleted by an attacker. This legitimate security tool, if leveraged by attackers, could be used to uncover additional vulnerabilities on target networks.

A server on the customer’s network was also observed writing the file “m.exe” to multiple internal devices. OSINT investigation into the executable indicated that it could be a malicious tool used to prevent antivirus programs from launching or running on a network [8].

Impact and Data Exfiltration

Following the initial steps of the breach chain, Darktrace observed numerous devices on the customer’s network engaging in data exfiltration and impact events, resulting in additional PTN alerts and a SOC investigation into data egress. Specifically, two servers on the network proceeded to read and download large volumes of data via SMB from multiple internal devices over the course of a few hours. These hosts sent large outbound volumes of data to MEGA file storage sites using TLS/SSL over port 443. Darktrace also identified the use of additional file storage services during this exfiltration event, including 4sync, file[.]io, and easyupload[.]io. In total the threat actor exfiltrated over 8.5 GB of data from the customer’s network.

Darktrace Cyber AI Analyst investigation highlighting the details of a data exfiltration attempt.
Figure 2: Darktrace Cyber AI Analyst investigation highlighting the details of a data exfiltration attempt.

Finally, Darktrace detected a user account within the customer’s Software-as-a-Service (SaaS) environment conducting several suspicious Office365 and AzureAD actions from a rare IP for the network, including uncommon file reads, creations and the deletion of a large number of files.

Unfortunately for the customer in this case, Darktrace RESPOND™ was not enabled on the network and the post-exploitation activity was able to progress until the customer was made aware of the attack by Darktrace’s SOC team. Had RESPOND been active and configured in autonomous response mode at the time of the attack, it would have been able to promptly contain the post-exploitation activity by blocking external connections, shutting down any C2 activity and preventing the download of suspicious files, blocking incoming traffic, and enforcing a learned ‘pattern of life’ on offending devices.

Conclusion

Given the widespread use of Netscaler Gateway and Netscaler ADC, Citrix Bleed remains an impactful and potentially disruptive vulnerability that will likely continue to affect organizations who fail to address affected assets. In this instance, Darktrace demonstrated its ability to track and inhibit malicious activity stemming from Citrix Bleed exploitation, enabling the customer to identify affected devices and enact their own remediation.

Darktrace’s anomaly-based approach to threat detection allows it to identify such post-exploitation activity resulting from the exploitation of a vulnerability, regardless of whether it is a known CVE or a zero-day threat. Unlike traditional security tools that rely on existing threat intelligence and rules and signatures, Darktrace’s ability to identify the subtle deviations in a compromised device’s behavior gives it a unique advantage when it comes to identifying emerging threats.

Credit to Vivek Rajan, Cyber Analyst, Adam Potter, Cyber Analyst

Appendices

Darktrace Model Coverage

Device / Suspicious SMB Scanning Activity

Device / ICMP Address Scan

Device / Possible SMB/NTLM Reconnaissance

Device / Network Scan

Device / SMB Lateral Movement

Device / Possible SMB/NTLM Brute Force

Device / Suspicious Network Scan Activity

User / New Admin Credentials on Server

Anomalous File / Internal::Unusual Internal EXE File Transfer

Compliance / SMB Drive Write

Device / New or Unusual Remote Command Execution

Anomalous Connection / New or Uncommon Service Control

Anomalous Connection / Rare WinRM Incoming

Anomalous Connection / Unusual Admin SMB Session

Device / Unauthorised Device

User / New Admin Credentials on Server

Anomalous Server Activity / Outgoing from Server

Device / Long Agent Connection to New Endpoint

Anomalous Connection / Multiple Connections to New External TCP Port

Device / New or Uncommon SMB Named Pipe

Device / Multiple Lateral Movement Model Breaches

Device / Large Number of Model Breaches

Compliance / Remote Management Tool On Server

Device / Anomalous RDP Followed By Multiple Model Breaches

Device / SMB Session Brute Force (Admin)

Device / New User Agent

Compromise / Large Number of Suspicious Failed Connections

Unusual Activity / Unusual External Data Transfer

Unusual Activity / Enhanced Unusual External Data Transfer

Device / Increased External Connectivity

Unusual Activity / Unusual External Data to New Endpoints

Anomalous Connection / Data Sent to Rare Domain

Anomalous Connection / Uncommon 1 GiB Outbound

Anomalous Connection / Active Remote Desktop Tunnel

Anomalous Server Activity / Anomalous External Activity from Critical Network Device

Compliance / Possible Unencrypted Password File On Server

Anomalous Connection / Suspicious Read Write Ratio and Rare External

Device / Reverse DNS Sweep]

Unusual Activity / Possible RPC Recon Activity

Anomalous File / Internal::Executable Uploaded to DC

Compliance / SMB Version 1 Usage

Darktrace AI Analyst Incidents

Scanning of Multiple Devices

Suspicious Remote Service Control Activity

SMB Writes of Suspicious Files to Multiple Devices

Possible SSL Command and Control to Multiple Devices

Extensive Suspicious DCE-RPC Activity

Suspicious DCE-RPC Activity

Internal Downloads and External Uploads

Unusual External Data Transfer

Unusual External Data Transfer to Multiple Related Endpoints

MITRE ATT&CK Mapping

Technique – Tactic – ID – Sub technique of

Network Scanning – Reconnaissance - T1595 - T1595.002

Valid Accounts – Defense Evasion, Persistence, Privilege Escalation, Initial Access – T1078 – N/A

Remote Access Software – Command and Control – T1219 – N/A

Lateral Tool Transfer – Lateral Movement – T1570 – N/A

Data Transfers – Exfiltration – T1567 – T1567.002

Compressed Data – Exfiltration – T1030 – N/A

NTLM Brute Force – Brute Force – T1110 - T1110.001

AntiVirus Deflection – T1553 - NA

Ingress Tool Transfer   - COMMAND AND CONTROL - T1105 - NA

Indicators of Compromise (IoCs)

204.155.149[.]37 – IP – Possible Malicious Endpoint

199.80.53[.]177 – IP – Possible Malicious Endpoint

168.100.9[.]137 – IP – Malicious Endpoint

45.134.26[.]2 – IP – Malicious Endpoint

13.35.147[.]18 – IP – Likely Malicious Endpoint

13.248.193[.]251 – IP – Possible Malicious Endpoint

76.223.1[.]166 – IP – Possible Malicious Endpoint

179.60.147[.]10 – IP – Likely Malicious Endpoint

185.220.101[.]25 – IP – Likely Malicious Endpoint

141.255.167[.]250 – IP – Malicious Endpoint

106.71.177[.]68 – IP – Possible Malicious Endpoint

cat2.hbwrapper[.]com – Hostname – Likely Malicious Endpoint

aj1090[.]online – Hostname – Likely Malicious Endpoint

dc535[.]4sync[.]com – Hostname – Likely Malicious Endpoint

204.155.149[.]140 – IP - Likely Malicious Endpoint

204.155.149[.]132 – IP - Likely Malicious Endpoint

204.155.145[.]52 – IP - Likely Malicious Endpoint

204.155.145[.]49 – IP - Likely Malicious Endpoint

References

  1. https://www.axios.com/2024/01/02/citrix-bleed-security-hacks-impact
  2. https://www.csoonline.com/article/1267774/hackers-steal-data-from-millions-of-xfinity-customers-via-citrix-bleed-vulnerability.html
  3. https://www.cybersecuritydive.com/news/citrixbleed-security-critical-vulnerability/702505/
  4. https://www.virustotal.com/gui/ip-address/168.100.9.137
  5. https://www.virustotal.com/gui/ip-address/45.134.26.2
  6. https://www.trendmicro.com/en_us/research/24/b/threat-actor-groups-including-black-basta-are-exploiting-recent-.html
  7. https://www.cisa.gov/news-events/cybersecurity-advisories/aa23-325a
  8. https://www.file.net/process/m.exe.html
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
Vivek Rajan
Cyber Analyst

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May 6, 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 6, 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
Your data. Our AI.
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