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July 6, 2023

How Darktrace Foiled QR Code Phishing

Explore Darktrace's successful detection of QR code phishing. Understand the methods used to thwart these sophisticated cyber threats.
Inside the SOC
Darktrace cyber analysts are world-class experts in threat intelligence, threat hunting and incident response, and provide 24/7 SOC support to thousands of Darktrace customers around the globe. Inside the SOC is exclusively authored by these experts, providing analysis of cyber incidents and threat trends, based on real-world experience in the field.
Written by
Alexandra Sentenac
Cyber Analyst
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06
Jul 2023

What is a QR Code?

Invented by a Japanese company in 1994 to label automobile parts, Quick Response codes, best known as QR codes, are rapidly becoming ubiquitous everywhere in the world. Their design, inspired by the board and black and white pieces of the game of Go, permits the storage of more information than regular barcodes and to access that information more quickly. The COVID-19 pandemic contributed to their increased popularity as it conveniently replaced physical media of all types for the purpose of content sharing. It is now common to see them in restaurant menus, plane tickets, advertisements and even in stickers containing minimal to no text pasted on lamp posts and other surfaces, enticing passers-by to scan its content. 

QR Code Phishing Attacks (Quishing)

Recently, threat actors have been identified using QR codes too to embed malicious URLs leading the unsuspecting user to compromised websites containing malware or designed to harvest credentials. In the past month, Darktrace has observed an increase in the number of phishing emails leveraging malicious QR codes for malware distribution and/or credential harvesting, a new form of social engineering attack labelled “Quishing” (i.e., QR code phishing).

Between June 13 and June 22, 2023, Darktrace protected a tech company against one such Quishing attack when five of its senior employees were sent malicious emails impersonating the company’s IT department. The emails contained a QR code that led to a login page designed to harvest the credentials of these senior staff members. Fortunately for the customer, Darktrace / EMAIL thwarted this phishing campaign in the first instance and the emails never reached the employee inboxes. 

Trends in Quishing Attacks

The Darktrace/Email team have noticed a recent and rapid increase in QR code abuse, suggesting that it is a growing tactic used by threat actors to deliver malicious payload links. This trend has also been observed by other security solutions [1] [2] [3] [4]. The Darktrace/Email team has identified malicious emails abusing QR codes in multiple ways. Examples include embedded image links which load a QR code and QR code images being delivered as attachments, such as those explored in this case study. Darktrace/Email is continually refining its detection of malicious QR codes and QR code extraction capabilities so that it can detect and block them regardless of their size and location within the email.   

Quishing Attack Overview

The attack consisted of five emails, each sent from different sender and envelope addresses, displayed common points between them. The emails all conveyed a sense of urgency, either via the use of words such as “urgent”, “now”, “required” or “important” in the subject field or by marking the email as high priority, thus making the recipient believe the message is pressing and requires immediate attention. 

Additionally, the subject of three of the emails directly referred to two factor authentication (2FA) enabling or QR code activation. Another particularity of these emails was that three of them attempted to impersonate the internal IT team of the company by inserting the company domain alongside strings, such as “it-desk” and “IT”, into the personal field of the emails. Email header fields like this are often abused by attackers to trick users by pretending to be an internal department or senior employee, thus avoiding more thorough validation checks. Both instilling a sense of urgency and including a known domain or name in the personal field are techniques that help draw attention to the email and maximize the chances that it is opened and engaged by the recipient. 

However, threat actors also need to make sure that the emails actually reach the intended inboxes, and this can be done in several ways. In this case, several tactics were employed. Two of the five emails were sent from legitimate sender addresses that successfully passed SPF validation, suggesting they were sent from compromised accounts. SPF is a standard email authentication method that tells the receiving email servers whether emails have been sent from authorized servers for a given domain. Without SPF validation, emails are more likely to be categorized as spam and be sent to the junk folder as they do not come from authorized sources.

Another of the malicious emails, which also passed SPF checks, used a health care facility company domain in the header-from address field but was actually sent from a different domain (i.e., envelope domain), which lowers the value of the SPF authentication. However, the envelope domain observed in this instance belonged to a company recently acquired by the tech company targeted by the campaign.

This shows a high level of targeting from the attackers, who likely hoped that this detail would make the email more familiar and less suspicious. In another case, the sender domain (i.e., banes-gn[.]com) had been created just 6 days prior, thus lowering the chances of there being open-source intelligence (OSINT) available on the domain. This reduces the chances of the email being detected by traditional email security solutions relying on signatures and known-bad lists.

Darktrace Detects Quishing Attack

Despite its novelty, the domain was detected and assessed as highly suspicious by Darktrace. Darktrace/Email was able to recognize all of the emails as spoofing and impersonation attempts and applied the relevant tags to them, namely “IT Impersonation” and “Fake Account Alert”, depending on the choice of personal field and subject. The senders of the five emails had no prior history or association with the recipient nor the company as no previous correspondence had been observed between the sender and recipient. The tags applied informed on the likely intent and nature of the suspicious indicators present in the email, as shown in Figure 1. 

Darktrace/Email UI
Figure 1: Email log overview page, displaying important information clearly and concisely. 

Quishing Attack Tactics

Minimal Plain Text

Another characteristic shared by these emails was that they had little to no text included in the body of the email and they did not contain a plain text portion, as shown in Figure 2. For most normal emails sent by email clients and most automated programs, an email will contain an HTML component and a text component, in addition to any potential attachments present. All the emails had one image attachment, suggesting the bulk of the message was displayed in the image rather than the email body. This hinders textual analysis and filtering of the email for suspicious keywords and language that could reveal its phishing intent. Additionally, the emails were well-formatted and used the logo of the well-known corporation Microsoft, suggesting some level of technical ability on the part of the attackers. 

Figure 2: Email body properties giving additional insights into the content of the email. 

Attachment and link payloads

The threat actors employed some particularly innovative and novel techniques with regards to the attachments and link payloads within these emails. As previously stated, all emails contained an image attachment and one or two links. Figure 3 shows that Darktrace/Email detected that the malicious links present in these emails were located in the attachments, rather than the body of the email. This is a technique often employed by threat actors to bypass link analysis by security gateways. Darktrace/Email was also able to detect this link as a QR code link, as shown in Figure 4.

Figure 3: Further properties and metrics regarding the location of the link within the email. 
Figure 4: Darktrace / EMAIL analyzes multiple metrics and properties related to links, some of which are detailed here. 

The majority of the text, as well as the malicious payload, was contained within the image attachment, which for one of the emails looked like this: 

example of quishing email
Figure 5: Redacted screenshot of the image payload contained in one of the emails. 

Convincing Appearance

As shown, the recipient is asked to setup 2FA authentication for their account within two days if they don’t want to be locked out. The visual formatting of the image, which includes a corporate logo and Privacy Statement and Acceptable Use Policy notices, is well balanced and convincing. The payload, in this case the QR code containing a malicious link, is positioned in the centre so as to draw attention and encourage the user to scan and click. This is a type of email employees are increasingly accustomed to receiving in order to log into corporate networks and applications. Therefore, recipients of such malicious emails might assume represents expected business activity and thus engage with the QR code without questioning it, especially if the email is claiming to be from the IT department.  

Malicious Redirection

Two of the Quishing emails contained links to legitimate file storage and sharing solutions Amazon Web Services (AWS) and and InterPlanetary File System (IPFS), whose domains are less likely to be blocked by traditional security solutions. Additionally, the AWS domain link contained a redirect to a different domain that has been flagged as malicious by multiple security vendors [5]. Malicious redirection was observed in four of the five emails, initially from well-known and benign services’ domains such as bing[.]com and login[.]microsoftonline[.]com. This technique allows attackers to hide the real destination of the link from the user and increase the likelihood that the link is clicked. In two of the emails, the redirect domain had only recently been registered, and in one case, the redirect domain observed was hosted on the new .zip top level domain (i.e., docusafe[.]zip). The domain name suggests it is attempting to masquerade as a compressed file containing important documentation. As seen in Figure 6, a new Darktrace/Email feature allows customers to safely view the final destination of the link, which in this case was a seemingly fake Microsoft login page which could be used to harvest corporate credentials.

Figure 6: Safe preview available from the Darktrace/Email Console showing the destination webpage of one of the redirect links observed.

Gathering Account Credentials

Given the nature of the landing page, it is highly likely that this phishing campaign had the objective of stealing the recipients’ credentials, as further indicated by the presence of the recipients’ email addresses in the links. Additionally, these emails were sent to senior employees, likely in an attempt to gather high value credentials to use in future attacks against the company. Had they succeeded, this would have represented a serious security incident, especially considering that 61% of attacks in 2023 involved stolen or hacked credentials according to Verizon’s 2023 data breach investigations report [6]. However, these emails received the highest possible anomaly score (100%) and were held by Darktrace/Email, thus ensuring that their intended recipients were never exposed to them. 

Looking at the indicators of compromise (IoCs) identified in this campaign, it appears that several of the IPs associated with the link payloads have been involved in previous phishing campaigns. Exploring the relations tab for these IPs in Virus Total, some of the communicating files appear to be .eml files and others have generic filenames including strings such as “invoice” “remittance details” “statement” “voice memo”, suggesting they have been involved in other phishing campaigns seemingly related to payment solicitation and other fraud attempts.

Figure 7: Virus Total’s relations tab for the IP 209.94.90[.]1 showing files communicating with the IP. 

Conclusion

Even though the authors of this Quishing campaign used all the tricks in the book to ensure that their emails would arrive unactioned by security tools to the targeted high value recipients’ inboxes, Darktrace/Email was able to immediately recognize the phishing attempts for what they were and block the emails from reaching their destination. 

This campaign used both classic and novel tactics, techniques, and procedures, but ultimately were detected and thwarted by Darktrace/Email. It is yet another example of the increasing attack sophistication mentioned in a previous Darktrace blog [7], wherein the attack landscape is moving from low-sophistication, low-impact, and generic phishing tactics to more targeted, sophisticated and higher impact attacks. Darktrace/Email does not rely on historical data nor known-bad lists and is best positioned to protect organizations from these highly targeted and sophisticated attacks.

References

[1] https://www.infosecurity-magazine.com/opinions/qr-codes-vulnerability-cybercrimes/ 

[2] https://www.helpnetsecurity.com/2023/03/21/qr-scan-scams/ 

[3] https://www.techtarget.com/searchsecurity/feature/Quishing-on-the-rise-How-to-prevent-QR-code-phishing 

[4] https://businessplus.ie/tech/qr-code-phishing-hp/ 

[5] https://www.virustotal.com/gui/domain/fistulacure.com

[6] https://www.verizon.com/business/en-gb/resources/reports/dbir/ ; https://www.verizon.com/business/en-gb/resources/reports/dbir/

[7] https://darktrace.com/blog/shifting-email-conversation 

Darktrace Model Detections 

Association models

No Sender or Content Association

New Sender

Unknown Sender

Low Sender Association

Link models

Focused Link to File Storage

Focused Rare Classified Links

New Unknown Hidden Redirect

High Risk Link + Low Sender Association

Watched Link Type

High Classified Link

File Storage From New

Hidden Link To File Storage

New Correspondent Classified Link

New Unknown Redirect

Rare Hidden Classified Link

Rare Hidden Link

Link To File Storage

Link To File Storage and Unknown Sender

Open Redirect

Unknown Sender Isolated Rare Link

Visually Prominent Link

Visually Prominent Link Unexpected For Sender

Low Link Association

Low Link Association and Unknown Sender

Spoof models

Fake Support Style

External Domain Similarities

Basic Known Entity Similarities

Unusual models

Urgent Request Banner

Urgent Request Banner + Basic Suspicious Sender

Very Young Header Domain

Young Header Domain

Unknown User Tracking

Unrelated Personal Name Address

Unrelated Personal Name Address + Freemail

Unusual Header TLD

Unusual Connection From Unknown

Unbroken Personal

Proximity models

Spam + Unknown Sender

Spam

Spam models

Unlikely Freemail Correspondence

Unlikely Freemail Personalization

General Indicators models

Incoming Mail Security Warning Message

Darktrace Model Tags

Credential Harvesting

Internal IT Impersonation

Multistage payload

Lookalike Domain

Phishing Link

Email Account Takeover

Fake Account Alert

Low Mailing History

No Association

Spoofing Indicators

Unknown Correspondent

VIP

Freemail

IoC - Type - Description & Confidence

fistulacure[.]com

domain

C2 Infrastructure

docusafe[.]zip

domain

Possible C2 Infrastructure

mwmailtec[.]com

domain

Possible C2 Infrastructure

czeromedia[.]com

domain

Possible C2 Infrastructure

192.40.165[.]109

IP address

Probable C2 Infrastructure

209.94.90[.]1

IP address

C2 Infrastructure

52.61.107[.]58

IP address

Possible C2 Infrastructure

40.126.32[.]133

IP address

Possible C2 Infrastructure

211.63.158[.]157

IP address

Possible C2 Infrastructure

119.9.27[.]129

IP address

Possible C2 Infrastructure

184.25.204[.]33

IP address

Possible C2 Infrastructure

40.107.8[.]107

IP address

Probable C2 Infrastructure

40.107.212[.]111

IP address

Possible Infrastructure

27.86.113[.]2

IP address

Possible C2 Infrastructure

192.40.191[.]19

IP address

Possible C2 Infrastructure

157.205.202[.]217

IP address

Possible C2 Infrastructure

a31f1f6063409ecebe8893e36d0048557142cbf13dbaf81af42bf14c43b12a48

SHA256 hash

Possible Malicious File

4c4fb35ab6445bf3749b9d0ab1b04f492f2bc651acb1bbf7af5f0a47502674c9

SHA256 hash

Possible Malicious File

f9c51d270091c34792b17391017a09724d9a7890737e00700dc36babeb97e252

SHA256 hash

Possible Malicious File

9f8ccfd616a8f73c69d25fd348b874d11a036b4d2b3fc7dbb99c1d6fa7413d9a

SHA256 hash

Possible Malicious File

b748894348c32d1dc5702085d70d846c6dd573296e79754df4857921e707c439

SHA256 hash

Possible Malicious File

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
Alexandra Sentenac
Cyber Analyst

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May 6, 2026

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

Software supply chain attacksDefault blog imageDefault blog image

Software supply-chain attacks in 2026

Software supply-chain attacks now represent the primary threat shaping the 2026 security landscape. Rather than relying on exploits at the perimeter, attackers are targeting the connective tissue of modern engineering environments: package managers, CI/CD automation, developer systems, and even the security tools organizations inherently trust.

These incidents are not isolated cases of poisoned code. They reflect a structural shift toward abusing trusted automation and identity at ecosystem scale, where compromise propagates through systems designed for speed, not scrutiny. Ephemeral build runners, regardless of provider, represent high‑trust, low‑visibility execution zones.

The Axios compromise and the cascading Trivy campaign illustrate how quickly this abuse can move once attacker activity enters build and delivery workflows. This blog provides an overview of the latest supply chain and security tool incidents with Darktrace telemetry and defensive actions to improve organizations defensive cyber posture.

1. Why the Axios Compromise Scaled

On 31 March 2026, attackers hijacked the npm account of Axios’s lead maintainer, publishing malicious versions 1.14.1 and 0.30.4 that silently pulled in a malicious dependency, plain‑crypto‑[email protected]. Axios is a popular HTTP client for node.js and  processes 100 million weekly downloads and appears in around 80% of cloud and application environments, making this a high‑leverage breach [1].

The attack chain was simple yet effective:

  • A compromised maintainer account enabled legitimate‑looking malicious releases.
  • The poisoned dependency executed Remote Access Trojans (RATs) across Linux, macOS and Windows systems.
  • The malware beaconed to a remote command-and-control (C2) server every 60 seconds in a loop, awaiting further instructions.
  • The installer self‑cleaned by deleting malicious artifacts.

All of this matters because a single maintainer compromise was enough to project attacker access into thousands of trusted production environments without exploiting a single vulnerability.

A view from Darktrace

Multiple cases linked with the Axios compromise were identified across Darktrace’s customer base in March 2026, across both Darktrace / NETWORK and Darktrace / CLOUD deployments.

In one Darktrace / CLOUD deployment, an Azure Cloud Asset was observed establishing new external HTTP connectivity to the IP 142.11.206[.]73 on port 8000. Darktrace deemed this activity as highly anomalous for the device based on several factors, including the rarity of the endpoint across the network and the unusual combination of protocol and port for this asset. As a result, the triggering the "Anomalous Connection / Application Protocol on Uncommon Port" model was triggered in Darktrace / CLOUD. Detection was driven by environmental context rather than a known indicator at the time. Subsequent reporting later classified the destination as malicious in relation to the Axios supply‑chain compromise, reinforcing the gap that often exists between initial attacker activity and the availability of actionable intelligence. [5]

Additionally, shortly before this C2 connection, the device was observed communicating with various endpoints associated with the NPM package manager, further reinforcing the association with this attack.

Darktrace’s detection of the unusual external connection to 142.11[.]206[.]73 via port 8000.  
Figure 1: Darktrace’s detection of the unusual external connection to 142.11[.]206[.]73 via port 8000.  

Within Axios cases observed within Darktrace / NETWORK customer environments, activity generally focused on the use of newly observed cURL user agents in outbound connections to the C2 URL sfrclak[.]com/6202033, alongside the download of malicious files.

In other cases, Darktrace / NETWORK customers with Microsoft Defender for Endpoint integration received alerts flagging newly observed system executables and process launches associated with C2 communication.

A Security Integration Alert from Microsoft Defender for Endpoint associated with the Axios supply chain attack.
Figure 2: A Security Integration Alert from Microsoft Defender for Endpoint associated with the Axios supply chain attack.

2. Why Trivy bypassed security tooling trust

Between late February and March 22, 2026, the threat group TeamPCP leveraged credentials from a previous incident to insert malicious artifacts across Trivy’s distribution ecosystem, including its CI automation, release binaries, Visual Studio Code extensions, and Docker container images [2].

While public reporting has emphasized GitHub Actions, Darktrace telemetry highlights attacker execution within CI/CD runner environments, including ephemeral build runners. These execution contexts are typically granted broad trust and limited visibility, allowing malicious activity within build automation to blend into expected operational workflows, regardless of provider.

This was a coordinated multi‑phase attack:

  • 75 of 76  of trivy-action tags and all setup‑trivy tags were force‑pushed to deliver a malicious payload.
  • A malicious binary (v0.69.4) was distributed across all major distribution channels.
  • Developer machines were compromised, receiving a persistent backdoor and a self-propagating worm.
  • Secrets were exfiltrated at scale, including SSH keys, Kuberenetes tokens, database passwords, and cloud credentials across Amazon Web Service (AWS), Azure, and Google Cloud Platform (GCP).

Within Darktrace’s customer base, an AWS EC2 instance monitored by Darktrace / CLOUD  appeared to have been impacted by the Trivy attack. On March 19, the device was seen connecting to the attacker-controlled C2 server scan[.]aquasecurtiy[.]org (45.148.10[.]212), triggering the model 'Anomalous Server Activity / Outgoing from Server’ in Darktrace / CLOUD.

Despite this limited historical context, Darktrace assessed this activity as suspicious due to the rarity of the destination endpoint across the wider deployment. This resulted in the triggering of a model alert and the generation of a Cyber AI Analyst incident to further analyze and correlate the attack activity.

TeamPCP’s continued abused of GitHub Actions against security and IT tooling has also been observed more recently in Darktrace’s customer base. On April 22, an AWS asset was seen connecting to the C2 endpoint audit.checkmarx[.]cx (94.154.172[.]43). The timing of this activity suggests a potential link to a malicious Bitwarden package distributed by the threat actor, which was only available for a short timeframe on April 22. [4][3]

Figure 3: A model alert flagging unusual external connectivity from the AWS asset, as seen in Darktrace / CLOUD .

While the Trivy activity originated within build automation, the underlying failure mode mirrors later intrusions observed via management tooling. In both cases, attackers leveraged platforms designed for scale and trust to execute actions that blended into normal operational noise until downstream effects became visible.

Quest KACE: Legacy Risk, Real Impact

The Quest KACE System Management Appliance (SMA) incident reinforces that software risk is not confined to development pipelines alone. High‑trust infrastructure and management platforms are increasingly leveraged by adversaries when left unpatched or exposed to the internet.

Throughout March 2026, attackers exploited CVE 2025-32975 to authentication on outdated, internet-facing KACE appliances, gaining administrative control and pushing remote payloads into enterprise environments. Organizations still running pre-patch versions effectively handed adversaries a turnkey foothold, reaffirming a simple strategic truth: legacy management systems are now part of the supply-chain threat surface, and treating them as “low-risk utilities” is no longer defensible [3].

Within the Darktrace customer base, a potential case was identified in mid-March involving an internet-facing server that exhibited the use of a new user agent alongside unusual file downloads and unexpected external connectivity. Darktrace identified the device downloading file downloads from "216.126.225[.]156/x", "216.126.225[.]156/ct.py" and "216.126.225[.]156/n", using the user agents, "curl/8.5.0" & "Python-urllib/3.9".

The timeframe and IoCs observed point towards likely exploitation of CVE‑2025‑32975. As with earlier incidents, the activity became visible through deviations in expected system behavior rather than through advance knowledge of exploitation or attacker infrastructure. The delay between observed exploitation and its addition to the Known Exploited Vulnerabilities (KEV) catalogue underscores a recurring failure: retrospective validation cannot keep pace with adversaries operating at automation speed.

The strategic pattern: Ecosystem‑scale adversaries

The Axios and Trivy compromises are not anomalies; they are signals of a structural shift in the threat landscape. In this post-trust era, the compromise of a single maintainer, repository token, or CI/CD tag can produce large-scale blast radiuses with downstream victims numbering in the thousands. Attackers are no longer just exploiting vulnerabilities; they are exploiting infrastructure privileges, developer trust relationships, and automated build systems that the industry has generally under secured.

Supply‑chain compromise should now be treated as an assumed breach scenario, not a specialized threat class, particularly across build, integration, and management infrastructure. Organizations must operate under the assumption that compromise will occur within trusted software and automation layers, not solely at the network edge or user endpoint. Defenders should therefore expect compromise to emerge from trusted automation layers before it is labelled, validated, or widely understood.

The future of supply‑chain defense lies in continuous behavioral visibility, autonomous detection across developer and build environments, and real‑time anomaly identification.

As AI increasingly shapes software development and security operations, defenders must assume adversaries will also operate with AI in the loop. The defensive edge will come not from predicting specific compromises, but from continuously interrogating behavior across environments humans can no longer feasibly monitor at scale.

Credit to Nathaniel Jones (VP, Security & AI Strategy, FCISCO), Emma Foulger (Global Threat Research Operations Lead), Justin Torres (Senior Cyber Analyst), Tara Gould (Malware Research Lead)

Edited by Ryan Traill (Content Manager)

Appendices

References:

1)         https://www.infosecurity-magazine.com/news/hackers-hijack-axios-npm-package/

2)         https://thehackernews.com/2026/03/trivy-hack-spreads-infostealer-via.html

3)         https://thehackernews.com/2026/03/hackers-exploit-cve-2025-32975-cvss-100.html

4)         https://www.endorlabs.com/learn/shai-hulud-the-third-coming----inside-the-bitwarden-cli-2026-4-0-supply-chain-attack

5)         https://socket.dev/blog/axios-npm-package-compromised?trk=public_post_comment-text

IoCs

- 142.11.206[.]73 – IP Address – Axios supply chain C2

- sfrclak[.]com – Hostname – Axios supply chain C2

- hxxp://sfrclak[.]com:8000/6202033 - URI – Axios supply chain payload

- 45.148.10[.]212 – IP Address – Trivy supply chain C2

- scan.aquasecurtiy[.]org – Hostname - Trivy supply chain C2

- 94.154.172[.]43 – IP Address - Checkmarx/Bitwarden supply chain C2

- audit.checkmarx[.]cx – Hostname - Checkmarx/Bitwarder supply chain C2

- 216.126.225[.]156 – IP Address – Quest KACE exploitation C2

- 216.126.225[.]156/32 - URI – Possible Quest KACE exploitation payload

- 216.126.225[.]156/ct.py - URI - Possible Quest KACE exploitation payload

- 216.126.225[.]156/n - URI - Possible Quest KACE exploitation payload

- 216.126.225[.]156/x - URI - Possible Quest KACE exploitation payload

- e1ec76a0e1f48901566d53828c34b5dc – MD5 - Possible Quest KACE exploitation payload

- d3beab2e2252a13d5689e9911c2b2b2fc3a41086 – SHA1 - Possible Quest KACE exploitation payload

- ab6677fcbbb1ff4a22cc3e7355e1c36768ba30bbf5cce36f4ec7ae99f850e6c5 – SHA256 - Possible Quest KACE exploitation payload

- 83b7a106a5e810a1781e62b278909396 – MD5 - Possible Quest KACE exploitation payload

- deb4b5841eea43cb8c5777ee33ee09bf294a670d – SHA1 - Possible Quest KACE exploitation payload

- b1b2f1e36dcaa36bc587fda1ddc3cbb8e04c3df5f1e3f1341c9d2ec0b0b0ffaf – SHA256 - Possible Quest KACE exploitation payload

Darktrace Model Detections

Anomalous Connection / Application Protocol on Uncommon Port

Anomalous Server Activity / Outgoing from Server

Anomalous Connection / New User Agent to IP Without Hostname

Anomalous File / EXE from Rare External Location

Anomalous File / Script from Rare External Location

Anomalous Server Activity / New User Agent from Internet Facing System

Anomalous Server Activity / Rare External from Server

Antigena / Network / External Threat / Antigena Suspicious File Block

Antigena / Network / External Threat / Antigena Suspicious File Pattern of Life Block

Device / New User Agent

Device / Internet Facing Device with High Priority Alert

Anomalous File / New User Agent Followed By Numeric File Download

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

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May 6, 2026

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

Default blog imageDefault blog image

What are email-delivered prompt injection attacks?

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

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

Recent examples of prompt injection attacks

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

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

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

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

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

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

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

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

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

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

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

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

How does Darktrace catch these types of attacks?

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

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

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

Ask your email provider about email-delivered AI prompt injection

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

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

Questions to ask your email security provider

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

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

Learn more about securing AI in your enterprise.

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