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June 5, 2025

Unpacking ClickFix: Darktrace’s detection of a prolific social engineering tactic

ClickFix is a social engineering technique that exploits human error through fake prompts, leading users to unknowingly run malicious commands. Learn how Darktrace detects and responds 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
Keanna Grelicha
Cyber Analyst
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05
Jun 2025

What is ClickFix and how does it work?

Amid heightened security awareness, threat actors continue to seek stealthy methods to infiltrate target networks, often finding the human end user to be the most vulnerable and easily exploited entry point.

ClickFix baiting is an exploitation of the end user, making use of social engineering techniques masquerading as error messages or routine verification processes, that can result in malicious code execution.

Since March 2024, the simplicity of this technique has drawn attention from a range of threat actors, from individual cybercriminals to Advanced Persistent Threat (APT) groups such as APT28 and MuddyWater, linked to Russia and Iran respectively, introducing security threats on a broader scale [1]. ClickFix campaigns have been observed affecting organizations in across multiple industries, including healthcare, hospitality, automotive and government [2][3].

Actors carrying out these targeted attacks typically utilize similar techniques, tools and procedures (TTPs) to gain initial access. These include spear phishing attacks, drive-by compromises, or exploiting trust in familiar online platforms, such as GitHub, to deliver malicious payloads [2][3]. Often, a hidden link within an email or malvertisements on compromised legitimate websites redirect the end user to a malicious URL [4]. These take the form of ‘Fix It’ or fake CAPTCHA prompts [4].

From there, users are misled into believing they are completing a human verification step, registering a device, or fixing a non-existent issue such as a webpage display error. As a result, they are guided through a three-step process that ultimately enables the execution of malicious PowerShell commands:

  1. Open a Windows Run dialog box [press Windows Key + R]
  2. Automatically or manually copy and paste a malicious PowerShell command into the terminal [press CTRL+V]
  3. And run the prompt [press ‘Enter’] [2]

Once the malicious PowerShell command is executed, threat actors then establish command and control (C2) communication within the targeted environment before moving laterally through the network with the intent of obtaining and stealing sensitive data [4]. Malicious payloads associated with various malware families, such as XWorm, Lumma, and AsyncRAT, are often deployed [2][3].

Attack timeline of ClickFix cyber attack

Based on investigations conducted by Darktrace’s Threat Research team in early 2025, this blog highlights Darktrace’s capability to detect ClickFix baiting activity following initial access.

Darktrace’s coverage of a ClickFix attack chain

Darktrace identified multiple ClickFix attacks across customer environments in both Europe, the Middle East, and Africa (EMEA) and the United States. The following incident details a specific attack on a customer network that occurred on April 9, 2025.

Although the initial access phase of this specific attack occurred outside Darktrace’s visibility, other affected networks showed compromise beginning with phishing emails or fake CAPTCHA prompts that led users to execute malicious PowerShell commands.

Darktrace’s visibility into the compromise began when the threat actor initiated external communication with their C2 infrastructure, with Darktrace / NETWORK detecting the use of a new PowerShell user agent, indicating an attempt at remote code execution.

Darktrace / NETWORK's detection of a device making an HTTP connection with new PowerShell user agent, indicating PowerShell abuse for C2 communications.
Figure 1: Darktrace / NETWORK's detection of a device making an HTTP connection with new PowerShell user agent, indicating PowerShell abuse for C2 communications.

Download of Malicious Files for Lateral Movement

A few minutes later, the compromised device was observed downloading a numerically named file. Numeric files like this are often intentionally nondescript and associated with malware. In this case, the file name adhered to a specific pattern, matching the regular expression: /174(\d){7}/. Further investigation into the file revealed that it contained additional malicious code designed to further exploit remote services and gather device information.

Figure 2: Darktrace / NETWORK's detection of a numeric file, one minute after the new PowerShell User Agent alert.

The file contained a script that sent system information to a specified IP address using an HTTP POST request, which also processed the response. This process was verified through packet capture (PCAP) analysis conducted by the Darktrace Threat Research team.

By analyzing the body content of the HTTP GET request, it was observed that the command converts the current time to Unix epoch time format (i.e., 9 April 2025 13:26:40 GMT), resulting in an additional numeric file observed in the URI: /1744205200.

PCAP highlighting the HTTP GET request that sends information to the specific IP, 193.36.38[.]237, which then generates another numeric file titled per the current time.
Figure 3: PCAP highlighting the HTTP GET request that sends information to the specific IP, 193.36.38[.]237, which then generates another numeric file titled per the current time.

Across Darktrace’s investigations into other customers' affected by ClickFix campaigns, both internal information discovery events and further execution of malicious code were observed.

Data Exfiltration

By following the HTTP stream in the same PCAP, the Darktrace Threat Research Team assessed the activity as indicative of data exfiltration involving system and device information to the same command-and-control (C2) endpoint, , 193.36.38[.]237. This endpoint was flagged as malicious by multiple open-source intelligence (OSINT) vendors [5].

PCAP highlighting HTTP POST connection with the numeric file per the URI /1744205200 that indicates data exfiltration to 193.36.38[.]237.
Figure 4: PCAP highlighting HTTP POST connection with the numeric file per the URI /1744205200 that indicates data exfiltration to 193.36.38[.]237.

Further analysis of Darktrace’s Advanced Search logs showed that the attacker’s malicious code scanned for internal system information, which was then sent to a C2 server via an HTTP POST request, indicating data exfiltration

Advanced Search further highlights Darktrace's observation of the HTTP POST request, with the second numeric file representing data exfiltration.
Figure 5: Advanced Search further highlights Darktrace's observation of the HTTP POST request, with the second numeric file representing data exfiltration.

Actions on objectives

Around ten minutes after the initial C2 communications, the compromised device was observed connecting to an additional rare endpoint, 188.34.195[.]44. Further analysis of this endpoint confirmed its association with ClickFix campaigns, with several OSINT vendors linking it to previously reported attacks [6].

In the final HTTP POST request made by the device, Darktrace detected a file at the URI /init1234 in the connection logs to the malicious endpoint 188.34.195[.]44, likely depicting the successful completion of the attack’s objective, automated data egress to a ClickFix C2 server.

Darktrace / NETWORK grouped together the observed indicators of compromise (IoCs) on the compromised device and triggered an Enhanced Monitoring model alert, a high-priority detection model designed to identify activity indicative of the early stages of an attack. These models are monitored and triaged 24/7 by Darktrace’s Security Operations Center (SOC) as part of the Managed Threat Detection service, ensuring customers are promptly notified of malicious activity as soon as it emerges.

Darktrace correlated the separate malicious connections that pertained to a single campaign.
Figure 6: Darktrace correlated the separate malicious connections that pertained to a single campaign.

Darktrace Autonomous Response

In the incident outlined above, Darktrace was not configured in Autonomous Response mode. As a result, while actions to block specific connections were suggested, they had to be manually implemented by the customer’s security team. Due to the speed of the attack, this need for manual intervention allowed the threat to escalate without interruption.

However, in a different example, Autonomous Response was fully enabled, allowing Darktrace to immediately block connections to the malicious endpoint (138.199.156[.]22) just one second after the initial connection in which a numerically named file was downloaded [7].

Darktrace Autonomous Response blocked connections to a suspicious endpoint following the observation of the numeric file download.
Figure 7: Darktrace Autonomous Response blocked connections to a suspicious endpoint following the observation of the numeric file download.

This customer was also subscribed to our Managed Detection and Response service, Darktrace’s SOC extended a ‘Quarantine Device’ action that had already been autonomously applied in order to buy their security team additional time for remediation.

Autonomous Response blocked connections to malicious endpoints, including 138.199.156[.]22, 185.250.151[.]155, and rkuagqnmnypetvf[.]top, and also quarantined the affected device. These actions were later manually reinforced by the Darktrace SOC.
Figure 8: Autonomous Response blocked connections to malicious endpoints, including 138.199.156[.]22, 185.250.151[.]155, and rkuagqnmnypetvf[.]top, and also quarantined the affected device. These actions were later manually reinforced by the Darktrace SOC.

Conclusion

ClickFix baiting is a widely used tactic in which threat actors exploit human error to bypass security defenses. By tricking end point users into performing seemingly harmless, everyday actions, attackers gain initial access to systems where they can access and exfiltrate sensitive data.

Darktrace’s anomaly-based approach to threat detection identifies early indicators of targeted attacks without relying on prior knowledge or IoCs. By continuously learning each device’s unique pattern of life, Darktrace detects subtle deviations that may signal a compromise. In this case, Darktrace's Autonomous Response, when operating in a fully autonomous mode, was able to swiftly contain the threat before it could progress further along the attack lifecycle.

Credit to Keanna Grelicha (Cyber Analyst) and Jennifer Beckett (Cyber Analyst)

Appendices

NETWORK Models

  • Device / New PowerShell User Agent
  • Anomalous Connection / New User Agent to IP Without Hostname
  • Anomalous Connection / Posting HTTP to IP Without Hostname
  • Anomalous Connection / Powershell to Rare External
  • Device / Suspicious Domain
  • Device / New User Agent and New IP
  • Anomalous File / New User Agent Followed By Numeric File Download (Enhanced Monitoring Model)
  • Device / Initial Attack Chain Activity (Enhanced Monitoring Model)

Autonomous Response Models

  • Antigena / Network::Significant Anomaly::Antigena Significant Anomaly from Client Block
  • Antigena / Network::Significant Anomaly::Antigena Enhanced Monitoring from Client Block
  • Antigena / Network::External Threat::Antigena File then New Outbound Block
  • Antigena / Network::External Threat::Antigena Suspicious File Block
  • Antigena / Network::Significant Anomaly::Antigena Alerts Over Time Block
  • Antigena / Network::External Threat::Antigena Suspicious File Block

IoC - Type - Description + Confidence

·       141.193.213[.]11 – IP address – Possible C2 Infrastructure

·       141.193.213[.]10 – IP address – Possible C2 Infrastructure

·       64.94.84[.]217 – IP address – Possible C2 Infrastructure

·       138.199.156[.]22 – IP address – C2 server

·       94.181.229[.]250 – IP address – Possible C2 Infrastructure

·       216.245.184[.]181 – IP address – Possible C2 Infrastructure

·       212.237.217[.]182 – IP address – Possible C2 Infrastructure

·       168.119.96[.]41 – IP address – Possible C2 Infrastructure

·       193.36.38[.]237 – IP address – C2 server

·       188.34.195[.]44 – IP address – C2 server

·       205.196.186[.]70 – IP address – Possible C2 Infrastructure

·       rkuagqnmnypetvf[.]top – Hostname – C2 server

·       shorturl[.]at/UB6E6 – Hostname – Possible C2 Infrastructure

·       tlgrm-redirect[.]icu – Hostname – Possible C2 Infrastructure

·       diagnostics.medgenome[.]com – Hostname – Compromised Website

·       /1741714208 – URI – Possible malicious file

·       /1741718928 – URI – Possible malicious file

·       /1743871488 – URI – Possible malicious file

·       /1741200416 – URI – Possible malicious file

·       /1741356624 – URI – Possible malicious file

·       /ttt – URI – Possible malicious file

·       /1741965536 – URI – Possible malicious file

·       /1.txt – URI – Possible malicious file

·       /1744205184 – URI – Possible malicious file

·       /1744139920 – URI – Possible malicious file

·       /1744134352 – URI – Possible malicious file

·       /1744125600 – URI – Possible malicious file

·       /1[.]php?s=527 – URI – Possible malicious file

·       34ff2f72c191434ce5f20ebc1a7e823794ac69bba9df70721829d66e7196b044 – SHA-256 Hash – Possible malicious file

·       10a5eab3eef36e75bd3139fe3a3c760f54be33e3 – SHA-1 Hash – Possible malicious file

MITRE ATT&CK Mapping

Tactic – Technique – Sub-Technique  

Spearphishing Link - INITIAL ACCESS - T1566.002 - T1566

Drive-by Compromise - INITIAL ACCESS - T1189

PowerShell - EXECUTION - T1059.001 - T1059

Exploitation of Remote Services - LATERAL MOVEMENT - T1210

Web Protocols - COMMAND AND CONTROL - T1071.001 - T1071

Automated Exfiltration - EXFILTRATION - T1020 - T1020.001

References

[1] https://www.logpoint.com/en/blog/emerging-threats/clickfix-another-deceptive-social-engineering-technique/

[2] https://www.proofpoint.com/us/blog/threat-insight/security-brief-clickfix-social-engineering-technique-floods-threat-landscape

[3] https://cyberresilience.com/threatonomics/understanding-the-clickfix-attack/

[4] https://www.group-ib.com/blog/clickfix-the-social-engineering-technique-hackers-use-to-manipulate-victims/

[5] https://www.virustotal.com/gui/ip-address/193.36.38.237/detection

[6] https://www.virustotal.com/gui/ip-address/188.34.195.44/community

[7] https://www.virustotal.com/gui/ip-address/138.199.156.22/detection

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
Keanna Grelicha
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

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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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