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November 7, 2022

[Part 1] Analysis of a Raccoon Stealer v1 Infection

Darktrace’s SOC team observed a fast-paced compromise involving Raccoon Stealer v1. See which steps the Raccoon Stealer v1 took to extract company data!
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
Mark Turner
SOC Shift Supervisor
Written by
Sam Lister
Specialist Security Researcher
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07
Nov 2022

Introduction

Towards the end of March 2022, the operators of Raccoon Stealer announced the closure of the Raccoon Stealer project [1]. In May 2022, Raccoon Stealer v2 was unleashed onto the world, with huge numbers of cases being detected across Darktrace’s client base. In this series of blog posts, we will follow the development of Raccoon Stealer between March and September 2022. We will first shed light on how Raccoon Stealer functioned before its demise, by providing details of a Raccoon Stealer v1 infection which Darktrace’s SOC saw within a client network on the 18th March 2022. In the follow-up post, we will provide details about the surge in Raccoon Stealer v2 cases that Darktrace’s SOC has observed since May 2022.  

What is Raccoon Stealer?

The misuse of stolen account credentials is a primary method used by threat actors to gain initial access to target environments [2]. Threat actors have several means available to them for obtaining account credentials. They may, for example, distribute phishing emails which trick their recipients into divulging account credentials. Alternatively, however, they may install information-stealing malware (i.e, info-stealers) onto users’ devices. The results of credential theft can be devastating. Threat actors may use the credentials to gain access to an organization’s SaaS environment, or they may use them to drain users’ online bank accounts or cryptocurrency wallets. 

Raccoon Stealer is a Malware-as-a-Service (MaaS) info-stealer first publicized in April 2019 on Russian-speaking hacking forums. 

Figure 1: One of the first known mentions of Raccoon Stealer on a Russian-speaking hacking forum named ‘Hack Forums’ on the 13th April 2019

The team of individuals behind Raccoon Stealer provide a variety of services to their customers (known as ‘affiliates’), including access to the info-stealer, an easy-to-use automated backend panel, hosting infrastructure, and 24/7 customer support [3]. 

Once Raccoon Stealer affiliates gain access to the info-stealer, it is up to them to decide how to distribute it. Since 2019, affiliates have been observed distributing the info-stealer via a variety of methods, such as exploit kits, phishing emails, and fake cracked software websites [3]/[4]. Once affiliates succeed in installing Raccoon Stealer onto target systems, the info-stealer will typically seek to obtain sensitive information saved in browsers and cryptocurrency wallets. The info-stealer will then exfiltrate the stolen data to a Command and Control (C2) server. The affiliate can then use the stolen data to conduct harmful follow-up activities. 

Towards the end of March 2022, the team behind Raccoon Stealer publicly announced that they would be suspending their operations after one of their core developers was killed during the Russia-Ukraine conflict [5]. 

Figure 2: Raccoon Stealer resignation post on March 25th 2022

Recent details shared by the US Department of Justice [6]/[7] indicate that it was in fact the arrest, rather than the death, of a key Raccoon Stealer operator which led the Raccoon Stealer team to suspend their operations [8].  

The closure of the Raccoon Stealer project, which ultimately resulted from the FBI-backed dismantling of Raccoon Stealer’s infrastructure in March 2022, did not last long, with the completion of Raccoon Stealer v2 being announced on the Raccoon Stealer Telegram channel on the 17th May 2022 [9]. 

 

Figure 3: Telegram post about new version of Raccoon Stealer

In the second part of this blog series, we will provide details of the recent surge in Raccoon Stealer v2 activity. In this post, however, we will provide insight into how the old version of Raccoon Stealer functioned just before its demise, by providing details of a Raccoon Stealer v1 infection which occurred on the 18th March 2022. 

Attack Details

On the 18th March, at around 13:00 (UTC), a user’s device within a customer’s network was seen contacting several websites providing fake cracked software. 

Figure 4: The above figure — obtained from the Darktrace Event Log for the infected device — highlights its connections to cracked software websites such as ‘licensekeysfree[.]com’ and ‘hdlicense[.]com’ before contacting ‘lion-files[.]xyz’ and ‘www.mediafire[.]com’

The user’s attempt to download cracked software from one of these websites resulted in their device making an HTTP GET request with a URI string containing ‘autodesk-revit-crack-v2022-serial-number-2022’ to an external host named ‘lion-filez[.]xyz’

Figure 5: Screenshot from hdlicense[.]com around the time of the infection shows a “Download” button linking to the ‘lion-filez[.]xyz’ endpoint

The device’s HTTP GET request to lion-filez[.]xyz was immediately followed by an HTTPS connection to the file hosting service, www.mediafire[.]com. Given that threat actors are known to abuse platforms such as MediaFire and Discord CDN to host their malicious payloads, it is likely that the user’s device downloaded the Raccoon Stealer v1 sample over its HTTPS connection to www.mediafire[.]com.  

After installing the info-stealer sample, the user’s device was seen making an HTTP GET request with the URI string ‘/g_shock_casio_easy’ to 194.180.191[.]185. The endpoint responded to the request with data related to a Telegram channel named ‘G-Shock’.

Figure 6: Telegram channel ‘@g_shock_casio_easy’

The returned data included the Telegram channel’s description, which in this case, was a base64 encoded and RC4 encrypted string of characters [10]/[11]. The Raccoon Stealer sample decoded and decrypted this string of characters to obtain its C2 IP address, 188.166.49[.]196. This technique used by Raccoon Stealer v1 closely mirrors the espionage method known as ‘dead drop’ — a method in which an individual leaves a physical object such as papers, cash, or weapons in an agreed hiding spot so that the intended recipient can retrieve the object later on without having to come in to contact with the source. In this case, the operators of Raccoon Stealer ‘left’ the malware’s C2 IP address within the description of a Telegram channel. Usage of this method allowed the operators of Raccoon Stealer to easily change the malware’s C2 infrastructure.  

After obtaining the C2 IP address from the ‘G-Shock’ Telegram channel, the Raccoon Stealer sample made an HTTP POST request with the URI string ‘/’ to the C2 IP address, 188.166.49[.]196. This POST request contained a Windows GUID,  a username, and a configuration ID. These details were RC4 encrypted and base64 encoded [12]. The C2 server responded to this HTTP POST request with JSON-formatted configuration information [13], including an identifier string, URL paths for additional files, along with several other fields. This configuration information was also concealed using RC4 encryption and base64 encoding.  

Figure 7- Fields within the JSON-formatted configuration data [13]

In this case, the server’s response included the identifier string ‘hv4inX8BFBZhxYvKFq3x’, along with the following URL paths:

  • /l/f/hv4inX8BFBZhxYvKFq3x/77d765d8831b4a7d8b5e56950ceb96b7c7b0ed70
  • /l/f/hv4inX8BFBZhxYvKFq3x/0cb4ab70083cf5985b2bac837ca4eacb22e9b711
  • /l/f/hv4inX8BFBZhxYvKFq3x/5e2a950c07979c670b1553b59b3a25c9c2bb899b
  • /l/f/hv4inX8BFBZhxYvKFq3x/2524214eeea6452eaad6ea1135ed69e98bf72979

After retrieving configuration data, the user’s device was seen making HTTP GET requests with the above URI strings to the C2 server. The C2 server responded to these requests with legitimate library files such as sqlite3.dll. Raccoon Stealer uses these libraries to extract data from targeted applications. 

Once the Raccoon Stealer sample had collected relevant data, it made an HTTP POST request with the URI string ‘/’ to the C2 server. This posted data likely included a ZIP file (named with the identifier string) containing stolen credentials [13]. 

The observed infection chain, which lasted around 20 minutes, consisted of the following steps:

1. User’s device installs Raccoon Stealer v1 samples from the user attempting to download cracked software

2. User’s device obtains the info-stealer’s C2 IP address from the description text of a Telegram channel

3. User’s device makes an HTTP POST request with the URI string ‘/’ to the C2 server. The request contains a Windows GUID,  a username, and a configuration ID. The response to the request contains configuration details, including an identifier string and URL paths for additional files

4. User’s device downloads library files from the C2 server

5. User’s device makes an HTTP POST request with the URI string ‘/’ to the C2 server. The request contains stolen data

Darktrace Coverage 

Although RESPOND/Network was not enabled on the customer’s deployment, DETECT picked up on several of the info-stealer’s activities. In particular, the device’s downloads of library files from the C2 server caused the following DETECT/Network models to breach:

  • Anomalous File / Masqueraded File Transfer
  • Anomalous File / EXE from Rare External Location
  • Anomalous File / Zip or Gzip from Rare External Location
  • Anomalous File / EXE from Rare External Location
  • Anomalous File / Multiple EXE from Rare External Locations
Figure 8: Event Log for the infected device shows 'Anomalous File / Masqueraded File Transfer' model breach after the device's download of a library file from the C2 server

Since the customer was subscribed to the Darktrace Proactive Threat Notification (PTN) service, they were proactively notified of the info-stealer’s activities. The quick response by Darktrace’s 24/7 SOC team helped the customer to contain the infection and to prevent further damage from being caused. Having been alerted to the info-stealer activity by the SOC team, the customer would also have been able to change the passwords for the accounts whose credentials were exfiltrated.

If RESPOND/Network had been enabled on the customer’s deployment, then it would have blocked the device’s connections to the C2 server, which would have likely prevented any stolen data from being exfiltrated.

Conclusion

Towards the end of March 2022, the team behind Raccoon Stealer announced that they would be suspending their operations. Recent developments suggest that the arrest of a core Raccoon Stealer developer was responsible for this suspension. Just before the Raccoon Stealer team were forced to shut down, Darktrace’s SOC team observed a Raccoon Stealer infection within a client’s network. In this post, we have provided details of the network-based behaviors displayed by the observed Raccoon Stealer sample. Since these v1 samples are no longer active, the details provided here are only intended to provide historical insight into the development of Raccoon Stealer’s operations and the activities carried out by Raccoon Stealer v1 just before its demise. In the next post of this series, we will discuss and provide details of Raccoon Stealer v2 — the new and highly prolific version of Raccoon Stealer. 

Thanks to Stefan Rowe and the Threat Research Team for their contributions to this blog.

References

[1] https://twitter.com/3xp0rtblog/status/1507312171914461188

[2] https://www.gartner.com/doc/reprints?id=1-29OTFFPI&ct=220411&st=sb

[3] https://www.cybereason.com/blog/research/hunting-raccoon-stealer-the-new-masked-bandit-on-the-block

[4] https://www.cyberark.com/resources/threat-research-blog/raccoon-the-story-of-a-typical-infostealer

[5] https://www.bleepingcomputer.com/news/security/raccoon-stealer-malware-suspends-operations-due-to-war-in-ukraine/

[6] https://www.justice.gov/usao-wdtx/pr/newly-unsealed-indictment-charges-ukrainian-national-international-cybercrime-operation

[7] https://www.youtube.com/watch?v=Fsz6acw-ZJY

[8] https://riskybiznews.substack.com/p/raccoon-stealer-dev-didnt-die-in

[9] https://medium.com/s2wblog/raccoon-stealer-is-back-with-a-new-version-5f436e04b20d

[10] https://blog.cyble.com/2021/10/21/raccoon-stealer-under-the-lens-a-deep-dive-analysis/

[11] https://decoded.avast.io/vladimirmartyanov/raccoon-stealer-trash-panda-abuses-telegram/

[12] https://blogs.blackberry.com/en/2021/09/threat-thursday-raccoon-infostealer

[13] https://cyberint.com/blog/research/raccoon-stealer/

Appendices

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
Mark Turner
SOC Shift Supervisor
Written by
Sam Lister
Specialist Security Researcher

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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
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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