ブログ
/
Network
/
June 19, 2023

Darktrace Detection of 3CX Supply Chain Attack

Explore how the 3CX supply chain compromise was uncovered, revealing key insights into the detection of sophisticated cyber 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
Nahisha Nobregas
SOC Analyst
Default blog imageDefault blog imageDefault blog imageDefault blog imageDefault blog imageDefault blog image
19
Jun 2023

Ever since the discovery of the SolarWinds hack that affected tens of thousands of organizations around the world in 2020, supply chain compromises have remained at the forefront of the minds of security teams and continue to pose a significant threat to their business operations. 

Supply chain compromises can have far-reaching implications, from disrupting an organization’s daily operations, incurring huge financial and reputational damage, to affecting the critical infrastructure of entire countries. As such, it is essential for organizations to have effective security measures in place able to identify and halt these attacks at the earliest possible stage.

In March 2023 the 3CX Desktop application became the latest victim of a supply chain compromise dubbed as the “SmoothOperator” by SentinelOne. This application is used by over 600,000 companies worldwide and the customer list contains high-profile customers across a variety of industries [2]. The 3CX Desktop application is a Voice over Internet Protocol (VoIP) communication software for enterprises that allows for chats, video calls, and voice calls. [3] The 3CX installers for both Windows and macOS systems were affected by information stealing malware. Researchers were able to discern that threat actors also known as UNC 4736 related to financially motivated North Korean operators also known as AppleJeus were responsible for the supply chain compromise.  Researchers have also linked it to another supply chain compromise that occurred prior on the Trading Technologies X_TRADER platform, making this the first known cascading software supply chain compromise used to distribute malware on a wide scale and still be able to align operator interests. [3] Customer reports following the compromise began to surface about the 3CX software being picked up as malicious by several cybersecurity vendors such as CrowdStrike, SentinelOne, and Palo Alto Networks. [6] 

By leveraging integrations with other security vendors like CrowdStrike and SentinelOne, Darktrace DETECT™ was able to identify activity from the “SmoothOperator” across the customer base at multiple stages of the kill chain in March 2023. Darktrace RESPOND™ was then able to autonomously intervene against these emerging threats, preventing significant disruption to customer networks. 

Background on the first known cascading supply chain attack 

Initial Access

In April 2023, security researchers identified the initial target in this story was not the 3CX desktop application, rather, it was another software application called X_TRADER by Trading Technologies. [3] Trading Technologies is a provider that offers high-performance financial trading packages, allowing financial professionals to analyze and trade assets within the stock market more efficiently. Unfortunately, a compromise already existed in the supply chain for this organization. The X_TRADER installer, which had been retired in 2020, still had its code signing certificate set to expire in October 2022. This code signing certificate was exploited by attackers to digitally sign the malicious software. [3] It also inopportunely led to 3CX when an employee unknowingly downloaded a trojanized installer for the X_TRADER software from Trading Technologies prior to the certificate’s expiration. [4]. This compromise of 3CX via X_TRADER was the first case of a cascading supply chain attack reported on within the wider threat landscape. 

Persistence and Privilege Escalation 

Following these findings, researchers were able to identify the likely kill chain that occurred on Windows systems, beginning with the download of the 3CX DesktopApp installer that executed an executable (.exe) file before dropping two trojanized Data Link Libraries (DLLs) alongside a benign executable that was used to sideload malicious DLLs. These DLLs contained and used SIGFLIP and DAVESHELL; both publicly available projects. [3] In this case, the DLLs were used to decrypt using an RC4 key and load a payload into the memory of a compromised system. [3] SIGFLIP and DAVESHELL also extract and decrypt the modular backdoor named VEILEDSIGNAL, which also contains a command and control (C2) configuration. This malware allowed the North Korean threat operators to gain administrative control to the 3CX employee’s device. [3] This was followed by access to the employee’s corporate credentials, ultimately leading to access to 3CX systems. [4] 

Lateral Movement and C2 activity

Security researchers were also able to identify other malware families that were mainly utilized in the supply chain attack to move laterally within the 3CX environment, and allow for C2 communication [3], these malware families are detailed below:

  • TaxHaul: when executed it decrypts shellcode payload, observed by Mandiant to persist via DLL search-order hijacking.
  • Coldcat: complex downloader, which also beacons to a C2 infrastructure.
  • PoolRat: collects system information and executes commands. This is the malware that was found to affect macOS systems.
  • IconicStealer: served as a third stage payload on 3CX systems to steal data or information.

Furthermore, it was also reported early on by Kaspersky that a backdoor named Gopuram, routinely used by the North Korean threat actors Lazarus and typically used against cryptocurrency companies, was also used as a second stage payload on a limited number of 3CX’s customers compromised systems. [5]

3CX detections observed by Darktrace

CrowdStrike and SentinelOne, two of the major detection platforms with which Darktrace partners through security integrations, initially revealed that their platforms had identified the campaign appeared to be targeting 3CXDesktopApp customers in March 2023. 

At this time, Darktrace was also observing this activity and alerting customers to unusual behavior on their networks. [1][7] Darktrace DETECT identified activity related to the supply chain compromise primarily through host-level alerts associated with CrowdStrike and SentinelOne integrations, as well as model breaches related to lateral movement and C2 activity. 

Some of the activity related to the 3CX supply chain compromise that Darktrace detected was observed solely via integration models picking up executable and Microsoft Software Installer (msi) file downloads for the 3CXDesktopApp, suggesting the compromise likely was stopped at the endpoint device. 

CrowdStrike integration model breach identifying 3CXDesktopApp[.]exe as possible malware
Figure 1: CrowdStrike integration model breach identifying 3CXDesktopApp[.]exe as possible malware on March 30, 2023.
showcases the Model Breach Event Log for the CrowdStrike integration model breach
Figure 2: The above figure, showcases the Model Breach Event Log for the CrowdStrike integration model breach shown in Figure 1.

In another case highlighted in Figure 3 and 4, security platforms were associating 3CX as malicious. The device in these figures was observed downloading a 3CXDesktopApp executable followed by an msi file about an hour later. This pattern of activity correlates with the compromise process that had been on reported, where the “SmoothOperator” malware that affected 3CX systems was able to persist through DLL side-loading of malicious DLL files delivered with benign executable files, making it difficult for traditional security tools to detect. [2][3][7]

The activity in this case was detected by the DETECT integration model, ‘High Severity Integration Malware Detection’ and was later blocked by the Darktrace RESPOND/Network model, ‘Antigena Significant Anomaly from Client Block’ which applied the “Enforce Pattern of Life” action to intercept the malicious download that was taking place. Darktrace RESPOND uses AI to learn every devices normal pattern of life and act autonomously to enforce its normal activity. In this event, RESPOND would not only intercept the malicious download that was taking place on the device, but also not allow the device to significantly deviate from its normal pattern of activity.

The Model Breach Event log for the device displays the moment in which the SentinelOne integration model breached for the 3CXDesktopApp.exe file
Figure 3: The Model Breach Event log for the device displays the moment in which the SentinelOne integration model breached for the 3CXDesktopApp.exe file followed subsequently by the RESPOND model, ‘Antigena Significant Anomaly from Client Block’, on March 29, 2023.
Another ‘High Severity Integration Malware Detection’ breached
Figure 4: Another ‘High Severity Integration Malware Detection’ breached for the same device in Figure 3 approximately one hour later because of the msi file, 3CXDesktopApp-18.12.416.msi, which also led to the Darktrace RESPOND model, ‘Antigena Significant Anomaly from Client Block’, on March 29, 2023.

In a separate case, Darktrace also detected a device performing unusual SMB drive writes for the file ‘3CXDesktopApp-18.10.461.msi’. This breached the DETECT model ‘SMB Drive Write’. This model detects when a device starts writing files to another internal device it does not usually communicate with via the SMB protocol using the admin$ or drive shares.

This Model Breach Event log highlights the moment Darktrace captured the msi application file for the 3CXDesktopApp being transferred internally on this customer’s network
Figure 5: This Model Breach Event log highlights the moment Darktrace captured the msi application file for the 3CXDesktopApp being transferred internally on this customer’s network, this was picked up as new activity for the device on March 28, 2023. 

In a couple of other cases observed by Darktrace, connections detected were made from affected devices to 3CX compromise related endpoints. In Figure 6, the device in question was detected connecting to the endpoint, journalide[.]org. This breached the model, ‘Suspicious Self-Signed SSL’, which looks for connections being made to an endpoint with a self-signed SSL certificate which is designed to look legitimate, as self-signed certificates are often used in malware communication.

Model Breach Event log for connections to the 3CX C2 related endpoint
Figure 6: Model Breach Event log for connections to the 3CX C2 related endpoint, journalide[.]org, these connections breached the model Suspicious Self-Signed SSL on April 24, 2023.

On another Darktrace customer environment, a 3CX C2 endpoint, pbxphonenetwork[.]com, had already been added to the Watched Domains list around the time reports of the 3CX application software being malicious had been reported. The Watched Domains list allows Darktrace to detect if any device on the network makes connections to these domains with more scrutiny and breach a model for further visibility of threats on the network. Activity in this case was detected and subsequently blocked by a Darktrace RESPOND action, “Block connections to 89.45.67[.]160 port 443 and pbxphonenetwork[.]com on port 443”, blocking the device from connecting to this 3CX C2 endpoints on the spot (see Figure 7). This activity subsequently breached the RESPOND model, ‘Antigena Watched Domain Block’. 

Figure 7: History log of the Darktrace RESPOND action applied to the device breaching the Darktrace RESPOND model, Antigena Watched Domain Block and applying the action, “Block connections to 89.45.67[.]160 port 443 and pbxphonenetwork[.]com on port 443” on March 31, 2023.

Darktrace Coverage 

Utilizing integrations with Darktrace such as those with CrowdStrike and SentinelOne, Darktrace was able to detect and respond to activity identified as malicious 3CX activity by CrowdStrike and SentinelOne as seen in Figures 1, 2, 3, and 4. This activity breached the following Darktrace DETECT models: 

  • Integration / CrowdStrike Alert
  • Security Integration / High Severity Integration Malware Detection

Darktrace was also able to identify lateral movement activity such as in the case illustrated in Figure 5.

  • Compliance / SMB Drive Write

Lastly, C2 beaconing activity from malicious endpoints associated with the 3CX compromise was also detected as seen in Figure 6, this activity breached the following Darktrace DETECT model:

  • Anomalous Connection / Suspicious Self-Signed SSL

For customers with Darktrace RESPOND configured in autonomous response mode, Darktrace RESPOND models also breached to activity related to the 3CX supply chain compromise as seen in Figures 3, 4, and 7. Below are the models that breached and the following autonomous actions that were applied:

  • Antigena / Network / Significant Anomaly / Antigena Significant Anomaly from Client Block, “Enforce pattern of life”
  • Antigena / Network / External Threat / Antigena Watched Domain Block, “Block connections to 89.45.67[.]160 port 443 and pbxphonenetwork[.]com on port 443”

Conclusion 

The first known cascading supply chain compromise occurred inopportunely for 3CX but conveniently for UNC 4736 North Korean threat actors. This “SmoothOperator” compromise was detected by endpoint security platforms such as CrowdStrike who was at the cusp of this discovery when it became one of the first platforms to report on malicious activity related to the 3CX DesktopApp supply chain compromise.  

Although still novel at the time and largely without reported indicators of compromise, Darktrace was able to capture and identify activity related to the 3CX compromise across its customer base, as well as respond autonomously to contain it. Darktrace was able to amplify security integrations with CrowdStrike and SentinelOne, and via anomaly-based model breaches, contribute unique insights by highlighting activity in varied parts of the 3CX supply chain compromise kill chain. The “SmoothOperator” supply chain attack proves that the Darktrace suite of products, including DETECT and RESPOND, can not only act autonomously to identify and respond to novel threats, but also work with security integrations to further amplify intervention and prevent cyber disruption on customer networks. 

Credit to Nahisha Nobregas, SOC Analyst and Trent Kessler, SOC Analyst.

Appendices

MITRE ATT&CK Framework

Resource Development

  • T1588 Obtain Capabilities  
  • T1588.004 Digital Certificates
  • T1608 Stage Capabilities  
  • T1608.003 Install Digital Certificate

Initial Access

  • T1190 Exploit Public-Facing Application
  • T1195 Supply Chain Compromise  
  • T1195.002 Compromise Software Supply Chain

Persistence

  • T1574 Hijack Execution Flow
  • T1574.002 DLL Side-Loading

Privilege Escalation

  • T1055 Process Injection
  • T1574 Hijack Execution Flow  
  • T1574.002 DLL Side-Loading

Command and Control

  • T1071 Application Layer Protocol
  • T1071.001 Web Protocols
  • T1071.004 DNS  
  • T1105 Ingress Tool Transfer
  • T1573 Encrypted Channel

List of IOCs

C2 Hostnames

  • journalide[.]org
  • pbxphonenetwork[.]com

Likely C2 IP address

  • 89.45.67[.]160

References

  1. https://www.crowdstrike.com/blog/crowdstrike-detects-and-prevents-active-intrusion-campaign-targeting-3cxdesktopapp-customers/
  2. https://www.bleepingcomputer.com/news/security/3cx-confirms-north-korean-hackers-behind-supply-chain-attack/
  3. https://www.mandiant.com/resources/blog/3cx-software-supply-chain-compromise
  4. https://www.securityweek.com/cascading-supply-chain-attack-3cx-hacked-after-employee-downloaded-trojanized-app/
  5. https://securelist.com/gopuram-backdoor-deployed-through-3cx-supply-chain-attack/109344/
  6. https://www.bleepingcomputer.com/news/security/3cx-hack-caused-by-trading-software-supply-chain-attack/
  7. https://www.sentinelone.com/blog/smoothoperator-ongoing-campaign-trojanizes-3cx-software-in-software-supply-chain-attack/
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
Nahisha Nobregas
SOC Analyst

More in this series

No items found.

Blog

/

Network

/

May 5, 2026

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

Default 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

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

Blog

/

Email

/

May 5, 2026

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

Default blog imageDefault blog image

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.

Continue reading
About the author
Kiri Addison
Senior Director of Product
あなたのデータ × DarktraceのAI
唯一無二のDarktrace AIで、ネットワークセキュリティを次の次元へ