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March 22, 2023

Amadey Info Stealer and N-Day Vulnerabilities

Understand the implications of the Amadey info stealer on cybersecurity and how it exploits N-day vulnerabilities for data theft.
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
Zoe Tilsiter
Cyber Analyst
Written by
The Darktrace Threat Research Team
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22
Mar 2023

The continued prevalence of Malware as a Service (MaaS) across the cyber threat landscape means that even the most inexperienced of would-be malicious actors are able to carry out damaging and wide-spread cyber-attacks with relative ease. Among these commonly employed MaaS are information stealers, or info-stealers, a type of malware that infects a device and attempts to gather sensitive information before exfiltrating it to the attacker. Info-stealers typically target confidential information, such as login credentials and bank details, and attempt to lie low on a compromised device, allowing access to sensitive data for longer periods of time. 

It is essential for organizations to have efficient security measures in place to defend their networks from attackers in an increasing versatile and accessible threat landscape, however incident response alone is not enough. Having an autonomous decision maker able to not only detect suspicious activity, but also take action against it in real time, is of the upmost importance to defend against significant network compromise. 

Between August and December 2022, Darktrace detected the Amadey info-stealer on more than 30 customer environments, spanning various regions and industry verticals across the customer base. This shows a continual presence and overlap of info-stealer indicators of compromise (IOCs) across the cyber threat landscape, such as RacoonStealer, which we discussed last November (Part 1 and Part 2).

Background on Amadey

Amadey Bot, a malware that was first discovered in 2018, is capable of stealing sensitive information and installing additional malware by receiving commands from the attacker. Like other malware strains, it is being sold in illegal forums as MaaS starting from $500 USD [1]. 

Researchers at AhnLab found that Amadey is typically distributed via existing SmokeLoader loader malware campaigns. Downloading cracked versions of legitimate software causes SmokeLoader to inject malicious payload into Windows Explorer processes and proceeds to download Amadey.  

The botnet has also been used for distributed denial of service (DDoS) attacks, and as a vector to install malware spam campaigns, such as LockBit 3.0 [2]. Regardless of the delivery techniques, similar patterns of activity were observed across multiple customer environments. 

Amadey’s primary function is to steal information and further distribute malware. It aims to extract a variety of information from infected devices and attempts to evade the detection of security measures by reducing the volume of data exfiltration compared to that seen in other malicious instances.

Darktrace DETECT/Network™ and its built-in features, such as Wireshark Packet Captures (PCAP), identified Amadey activity on customer networks, whilst Darktrace RESPOND/Network™ autonomously intervened to halt its progress.

Attack Details

Figure 1: Timeline of Amadey info-stealer kill chain.

Initial Access  

User engagement with malicious email attachments or cracked software results in direct execution of the SmokeLoader loader malware on a device. Once the loader has executed its payload, it is then able to download additional malware, including the Amadey info-stealer.

Unusual Outbound Connections 

After initial access by the loader and download of additional malware, the Amadey info-stealer captures screenshots of network information and sends them to Amadey command and control (C2) servers via HTTP POST requests with no GET to a .php URI. An example of this can be seen in Figure 2.  

Figure 2: PCAP from an affected customer showing screenshots being sent out to the Amadey C2 server via a .jpg file. 

C2 Communications  

The infected device continues to make repeated connections out to this Amadey endpoint. Amadey's C2 server will respond with instructions to download additional plugins in the form of dynamic-link libraries (DLLs), such as "/Mb1sDv3/Plugins/cred64.dll", or attempt to download secondary info-stealers such as RedLine or RaccoonStealer. 

Internal Reconnaissance 

The device downloads executable and DLL files, or stealer configuration files to steal additional network information from software including RealVNC and Outlook. Most compromised accounts were observed downloading additional malware following commands received from the attacker.

Data Exfiltration 

The stolen information is then sent out via high volumes of HTTP connection. It makes HTTP POSTs to malicious .php URIs again, this time exfiltrating more data such as the Amadey version, device names, and any anti-malware software installed on the system.

How did the attackers bypass the rest of the security stack?

Existing N-Day vulnerabilities are leveraged to launch new attacks on customer networks and potentially bypass other tools in the security stack. Additionally, exfiltrating data via low and slow HTTP connections, rather than large file transfers to cloud storage platforms, is an effective means of evading the detection of traditional security tools which often look for large data transfers, sometimes to a specific list of identified “bad” endpoints.

Darktrace Coverage 

Amadey activity was autonomously identified by DETECT and the Cyber AI Analyst. A list of DETECT models that were triggered on deployments during this kill chain can be found in the Appendices. 

Various Amadey activities were detected and highlighted in DETECT model breaches and their model breach event logs. Figure 3 shows a compromised device making suspicious HTTP POST requests, causing the ‘Anomalous Connection / Posting HTTP to IP Without Hostname’ model to breach. It also downloaded an executable file (.exe) from the same IP.

Figure 3: Amadey activity on a customer deployment captured by model breaches and event logs. 

DETECT’s built-in features also assisted with detecting the data exfiltration. Using the PCAP integration, the exfiltrated data was captured for analysis. Figure 4 shows a connection made to the Amadey endpoint, in which information about the infected device, such as system ID and computer name, were sent. 

Figure 4: PCAP downloaded from Darktrace event logs highlighting data egress to the Amadey endpoint. 

Further information about the infected system can be seen in the above PCAP. As outlined by researchers at Ahnlab and shown in Figure 5, additional system information sent includes the Amadey version (vs=), the device’s admin privilege status (ar=), and any installed anti-malware or anti-virus software installed on the infected environment (av=) [3]. 

Figure 5: AhnLab’s glossary table explaining the information sent to the Amadey C2 server. 

Darktrace’s AI Analyst was also able to connect commonalities between model breaches on a device and present them as a connected incident made up of separate events. Figure 6 shows the AI Analyst incident log for a device having breached multiple models indicative of the Amadey kill chain. It displays the timeline of these events, the specific IOCs, and the associated attack tactic, in this case ‘Command and Control’. 

Figure 6: A screenshot of multiple IOCs and activity correlated together by AI Analyst. 

When enabled on customer’s deployments, RESPOND was able to take immediate action against Amadey to mitigate its impact on customer networks. RESPOND models that breached include: 

  • Antigena / Network / Significant Anomaly / Antigena Significant Anomaly from Client Block
  • Antigena / Network / External Threat / Antigena Suspicious File Block 
  • Antigena / Network / Significant Anomaly / Antigena Controlled and Model Breach

On one customer’s environment, a device made a POST request with no GET to URI ‘/p84Nls2/index.php’ and unepeureyore[.]xyz. RESPOND autonomously enforced a previously established pattern of life on the device twice for 30 minutes each and blocked all outgoing traffic from the device for 10 minutes. Enforcing a device’s pattern of life restricts it to conduct activity within the device and/or user’s expected pattern of behavior and blocks anything anomalous or unexpected, enabling normal business operations to continue. This response is intended to reduce the potential scale of attacks by disrupting the kill chain, whilst ensuring business disruption is kept to a minimum. 

Figure 7: RESPOND actions taken on a customer deployment to disrupt the Amadey kill chain. 

The Darktrace Threat Research team conducted thorough investigations into Amadey activity observed across the customer base. They were able to identify and contextualize this threat across the fleet, enriching AI insights with collaborative human analysis. Pivoting from AI insights as their primary source of information, the Threat Research team were able to provide layered analysis to confirm this campaign-like activity and assess the threat across multiple unique environments, providing a holistic assessment to customers with contextualized insights.

Conclusion

The presence of the Amadey info-stealer in multiple customer environments highlights the continuing prevalence of MaaS and info-stealers across the threat landscape. The Amadey info-stealer in particular demonstrates that by evading N-day vulnerability patches, threat actors routinely launch new attacks. These malicious actors are then able to evade detection by traditional security tools by employing low and slow data exfiltration techniques, as opposed to large file transfers.

Crucially, Darktrace’s AI insights were coupled with expert human analysis to detect, respond, and provide contextualized insights to notify customers of Amadey activity effectively. DETECT captured Amadey activity taking place on customer deployments, and where enabled, RESPOND’s autonomous technology was able to take immediate action to reduce the scale of such attacks. Finally, the Threat Research team were in place to provide enhanced analysis for affected customers to help security teams future-proof against similar attacks.

Appendices

Darktrace Model Detections 

Anomalous File / EXE from Rare External Location

Device / Initial Breach Chain Compromise

Anomalous Connection / Posting HTTP to IP Without Hostname 

Anomalous Connection / POST to PHP on New External Host

Anomalous Connection / Multiple HTTP POSTs to Rare Hostname 

Compromise / Beaconing Activity To External Rare

Compromise / Slow Beaconing Activity To External Rare

Anomalous Connection / Multiple Failed Connections to Rare Endpoint

List of IOCs

f0ce8614cc2c3ae1fcba93bc4a8b82196e7139f7 - SHA1 - Amadey DLL File Hash

e487edceeef3a41e2a8eea1e684bcbc3b39adb97 - SHA1 - Amadey DLL File Hash

0f9006d8f09e91bbd459b8254dd945e4fbae25d9 - SHA1 - Amadey DLL File Hash

4069fdad04f5e41b36945cc871eb87a309fd3442 - SHA1 - Amadey DLL File Hash

193.106.191[.]201 - IP - Amadey C2 Endpoint

77.73.134[.]66 - IP - Amadey C2 Endpoint

78.153.144[.]60 - IP - Amadey C2 Endpoint

62.204.41[.]252 - IP - Amadey C2 Endpoint

45.153.240[.]94 - IP - Amadey C2 Endpoint

185.215.113[.]204 - IP - Amadey C2 Endpoint

85.209.135[.]11 - IP - Amadey C2 Endpoint

185.215.113[.]205 - IP - Amadey C2 Endpoint

31.41.244[.]146 - IP - Amadey C2 Endpoint

5.154.181[.]119 - IP - Amadey C2 Endpoint

45.130.151[.]191 - IP - Amadey C2 Endpoint

193.106.191[.]184 - IP - Amadey C2 Endpoint

31.41.244[.]15 - IP - Amadey C2 Endpoint

77.73.133[.]72 - IP - Amadey C2 Endpoint

89.163.249[.]231 - IP - Amadey C2 Endpoint

193.56.146[.]243 - IP - Amadey C2 Endpoint

31.41.244[.]158 - IP - Amadey C2 Endpoint

85.209.135[.]109 - IP - Amadey C2 Endpoint

77.73.134[.]45 - IP - Amadey C2 Endpoint

moscow12[.]at - Hostname - Amadey C2 Endpoint

moscow13[.]at - Hostname - Amadey C2 Endpoint

unepeureyore[.]xyz - Hostname - Amadey C2 Endpoint

/fb73jc3/index.php - URI - Amadey C2 Endpoint

/panelis/index.php - URI - Amadey C2 Endpoint

/panelis/index.php?scr=1 - URI - Amadey C2 Endpoint

/panel/index.php - URI - Amadey C2 Endpoint

/panel/index.php?scr=1 - URI - Amadey C2 Endpoint

/panel/Plugins/cred.dll - URI - Amadey C2 Endpoint

/jg94cVd30f/index.php - URI - Amadey C2 Endpoint

/jg94cVd30f/index.php?scr=1 - URI - Amadey C2 Endpoint

/o7Vsjd3a2f/index.php - URI - Amadey C2 Endpoint

/o7Vsjd3a2f/index.php?scr=1 - URI - Amadey C2 Endpoint

/o7Vsjd3a2f/Plugins/cred64.dll - URI - Amadey C2 Endpoint

/gjend7w/index.php - URI - Amadey C2 Endpoint

/hfk3vK9/index.php - URI - Amadey C2 Endpoint

/v3S1dl2/index.php - URI - Amadey C2 Endpoint

/f9v33dkSXm/index.php - URI - Amadey C2 Endpoint

/p84Nls2/index.php - URI - Amadey C2 Endpoint

/p84Nls2/Plugins/cred.dll - URI - Amadey C2 Endpoint

/nB8cWack3/index.php - URI - Amadey C2 Endpoint

/rest/index.php - URI - Amadey C2 Endpoint

/Mb1sDv3/index.php - URI - Amadey C2 Endpoint

/Mb1sDv3/index.php?scr=1 - URI - Amadey C2 Endpoint

/Mb1sDv3/Plugins/cred64.dll  - URI - Amadey C2 Endpoint

/h8V2cQlbd3/index.php - URI - Amadey C2 Endpoint

/f5OknW/index.php - URI - Amadey C2 Endpoint

/rSbFldr23/index.php - URI - Amadey C2 Endpoint

/rSbFldr23/index.php?scr=1 - URI - Amadey C2 Endpoint

/jg94cVd30f/Plugins/cred64.dll - URI - Amadey C2 Endpoint

/mBsjv2swweP/Plugins/cred64.dll - URI - Amadey C2 Endpoint

/rSbFldr23/Plugins/cred64.dll - URI - Amadey C2 Endpoint

/Plugins/cred64.dll - URI - Amadey C2 Endpoint

Mitre Attack and Mapping 

Collection:

T1185 - Man the Browser

Initial Access and Resource Development:

T1189 - Drive-by Compromise

T1588.001 - Malware

Persistence:

T1176 - Browser Extensions

Command and Control:

T1071 - Application Layer Protocol

T1071.001 - Web Protocols

T1090.002 - External Proxy

T1095 - Non-Application Layer Protocol

T1571 - Non-Standard Port

T1105 - Ingress Tool Transfer

References 

[1] https://malpedia.caad.fkie.fraunhofer.de/details/win.amadey

[2] https://asec.ahnlab.com/en/41450/

[3] https://asec.ahnlab.com/en/36634/

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
Zoe Tilsiter
Cyber Analyst
Written by
The Darktrace Threat Research Team

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May 5, 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 5, 2026

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

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What are email-delivered prompt injection attacks?

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

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

Recent examples of prompt injection attacks

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

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

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

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

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

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

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

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

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

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

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

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

How does Darktrace catch these types of attacks?

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

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

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

Ask your email provider about email-delivered AI prompt injection

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

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

Questions to ask your email security provider

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

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

Learn more about securing AI in your enterprise.

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About the author
Kiri Addison
Senior Director of Product
Your data. Our AI.
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