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October 13, 2023

Protecting Brazilian Organizations from Malware

Discover how Darktrace DETECT thwarted a banking trojan targeting Brazilian organizations, preventing data theft and informing the customer.
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
Roberto Romeu
Senior SOC Analyst
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13
Oct 2023

Nationally Targeted Cyber Attacks

As the digital world becomes more and more interconnected, the threat of cyber-attacks transcends borders and presents a significant concern to security teams worldwide. Yet despite this, some malicious actors have shown a tendency to focus their attacks on specific countries. By employing highly tailored tactics, techniques, and procedures (TTPs) to target users and organizations from one nation, rather than launching more widespread campaigns, threat actors are able to maximize the efficiency and efficacy of their attacks.

What is Guildma and how does it work?

One example can be seen in the remote access trojan (RAT) and information stealer, Guildma. Guildma, also known by the demonic moniker, Astaroth, first appeared in the wild in 2017 and is a Latin America-based banking trojan known to primarily target organizations in Brazil, although has more recently been observed in North America and Europe too [1].

By concentrating their efforts on Brazil, Guildma is able to launch attacks with a high degree of specificity, focussing their language on Brazilian norms, referencing Brazilian institutions, and tailoring their social engineering accordingly. Moreover, considering that Brazilian customers likely represent a relatively small portion of security vendors’ clientele, there may be a limited pool of available indicators of compromise (IoCs). This limitation could significantly impact the efficacy of traditional security measures that rely on signature-based detection methods in identifying emerging threats.

Darktrace vs. Guildma

In June 2023, Darktrace observed a Guildma compromise on the network of a Brazilian customer in the manufacturing sector. The anomaly-based detection capabilities of Darktrace DETECT™ allowed it to identify suspicious activity surrounding the compromise, agnostic of any IoCs or specific signatures of a threat actor. Following the successful detection of the malware, the Darktrace Security Operations Center (SOC) carried out a thorough investigation into the compromise and brought it to the attention of the customer’s security team, allowing them to quickly react and prevent any further escalation.

This early detection by Darktrace effectively shut down Guildma operations on the network before any sensitive data could be gathered and stolen by malicious actors.

Attack Overview

In the case of the Guildma RAT detected by Darktrace, the affected system was a desktop device, ostensibly used by one employee. The desktop was first observed on the customer’s network in April 2023; however, it is possible that the initial compromise took place before Darktrace had visibility over the network. Guildma compromises typically start with phishing campaigns, indicating that the initial intrusion in this case likely occurred beyond the scope of Darktrace’s monitoring [2].

Early indicators

On June 23, 2023, Darktrace DETECT observed the first instance of unusual activity being performed by the affected desktop device, namely regular HTTP POST requests to a suspicious domain, indicative of command-and-control (C2) beaconing activity. The domain used an unusual Top-Level Domain (TLD), with a plausibly meaningful (in Portuguese) second-level domain and a seemingly random 11-character third-level domain, “dn00x1o0f0h.puxaofolesanfoneiro[.]quest”.

Throughout the course of this attack, Darktrace observed additional connections like this, representing something of a signature of the attack. The suspicious domains were typically registered within six months of observation, featured an uncommon TLD, and included a seemingly randomized third-level domain of 6-11 characters, followed by a plausibly legitimate second-level domain with a minimum of 15 characters. The connections to these unusual endpoints all followed a similar two-hour beaconing period, suggesting that Guildma may rotate its C2 infrastructure, using the Multi-Stage Channels TTP (MITRE ID T1104) to evade restrictions by firewalls or other signature-based security tools that rely on static lists of IoCs and “known bads”.

Figure 1: Model Breach Event Log for the “Compromise / Agent Beacon (Long Period)”. The connections at two-hour intervals, including at unreasonably late hours, is consistent with beaconing for C2.

Living-off-the-land with BITS abuse

A week later, on June 30, 2023, the affected device was observed making an unusual Microsoft BITS connection. BitsAdmin is a deprecated administrative tool available on most Windows devices and can be leveraged by attackers to transfer malicious obfuscated payloads into and around an organization’s network. The domain observed during this connection, "cwiufv.pratkabelhaemelentmarta[.]shop”, follows the previously outlined domain naming convention. Multiple open-source intelligence (OSINT) sources indicated that the endpoint had links to malware and, when visited, redirected users to the Brazilian versions of WhatsApp and Zoom. This is likely a tactic employed by threat actors to ensure users are unaware of suspicious domains, and subsequent malware downloads, by redirected them to a trusted source.

Figure 2: A screenshot of the Model Breach log summary of the “Unusual BITS Activity” model breach. The breach log contains key details such as the ASN, hostname, and user agent used in the breaching connection.

Obfuscated Tooling Downloads

Within one minute of the suspicious BITS activity, Darktrace detected the device downloading a suspicious file from the aforementioned endpoint, (cwiufv.pratkabelhaemelentmarta[.]shop). The file in question appeared to be a ZIP file with the 17-digit numeric name query, namely “?37627343830628786”, with the filename “zodzXLWwaV.zip”.

However, Darktrace DETECT recognized that the file extension did not match its true file type and identified that it was, in fact, an executable (.exe) file masquerading as a ZIP file. By masquerading files downloads, threat actors are able to make their malicious files seem legitimate and benign to security teams and traditional security tools, thereby evading detection. In this case, the suspicious file in question was indeed identified as malicious by multiple OSINT sources.

Following the initial download of this masqueraded file, Darktrace also detected subsequent downloads of additional executable files from the same endpoint.  It is possible that these downloads represented Guildma actors attempting to download additional tooling, including the information-stealer widely known as Astaroth, in order to begin its data collection and exfiltration operations.

Figure 3: A screenshot of a graph produced by the Threat Visualizer of the affected device's external connections. The visual aid marks breaches with red and orange dots, creating a more intuitive explanation of observed behavior.

Darktrace SOC

The successful detection of the masqueraded file transfer triggered an Enhanced Monitoring model breach, a high-fidelity model designed to detect activity that is more likely indicative of an ongoing compromise.  

This breach was immediately escalated to the Darktrace SOC for analysis by Darktrace’s team of expert analysts who were able to complete a thorough investigation and notify the customer’s security team of the compromise in just over half an hour. The investigation carried out by Darktrace’s analysts confirmed that the activity was, indeed, malicious, and provided the customer’s security team with details around the extent of the compromise, the specific IoCs, and risks this compromise posed to their digital environment. This information empowered the customer’s security team to promptly address the issue, having a significant portion of the investigative burden reduced and resolved by the round-the-clock Darktrace analyst team.

In addition to this, Cyber AI Analyst™ launched an investigation into the ongoing compromise and was able to connect the anomalous HTTP connections to the subsequent suspicious file downloads, viewing them as one incident rather than two isolated events. AI Analyst completed its investigation in just three minutes, upon which it provided a detailed summary of events of the activity, further aiding the customer’s remediation process.

Figure 4: CyberAI Analyst summary of the suspicious activity. A prose summary of the breach activity and the meaning of the technical details is included to maintain an easily digestible stream of information.

Conclusion

While the combination of TTPs observed in this Guildma RAT compromise is not uncommon globally, the specificity to targeting organizations in Brazil allows it to be incredibly effective. By focussing on just one country, malicious actors are able to launch highly specialized attacks, adapting the language used and tailoring the social engineering effectively to achieve maximum success. Moreover, as Brazil likely represents a smaller segment of security vendors’ customers, therefore leading to a limited pool of IoCs, attackers are often able to evade traditional signature-based detections.

Darktrace DETECT’s anomaly-based approach to threat detection allows for effective detection, mitigation, and response to emerging threats, regardless of the specifics of the attack and without relying on threat intelligence or previous IoCs. Ultimately in this case, Darktrace was able to identify the suspicious activity surrounding the Guildma compromise and swiftly bring it to the attention of the customer’s security team, before any data gathering, or exfiltration activity took place.

Darktrace’s threat detection capabilities coupled with its expert analyst team and round-the-clock SOC response is a highly effective addition to an organization’s defense-in-depth, whether in Brazil or anywhere else around the world.

Credit to Roberto Romeu, Senior SOC Analyst, Taylor Breland, Analyst Team Lead, San Francisco

References

https://malpedia.caad.fkie.fraunhofer.de/details/win.astaroth

https://www.welivesecurity.com/2020/03/05/guildma-devil-drives-electric/  

Appendices

Darktrace DETECT Model Breaches

  • Compromise / Agent Beacon (Long Period)
  • Device / Unusual BITS Activity
  • Anomalous File / Anomalous Octet Stream (No User Agent)
  • Anomalous File / Masqueraded File Transfer (Enhanced Monitoring Model)
  • Anomalous File / EXE from Rare External Location
  • Anomalous File / Multiple EXE from Rare External Locations

List of IoCs

IoC Type - Description + Confidence

5q710e1srxk.broilhasoruikaliventiladorrta[.]shop - Domain - Likely C2 server

m2pkdlse8md.roilhasohlcortinartai[.]hair - Domain - Likely C2 server

cwiufv.pratkabelhaemelentmarta[.]shop - Domain - C2 server

482w5pct234.jaroilcasacorkalilc[.]ru[.]com - Domain - C2 server

dn00x1o0f0h.puxaofolesanfoneiro[.]quest - Domain - Likely C2 server

10v7mybga55.futurefrontier[.]cyou - Domain - Likely C2 server

f788gbgdclp.growthgenerator[.]cyou - Domain - Likely C2 server

6nieek.satqabelhaeiloumelsmarta[.]shop - Domain - Likely C2 server

zodzXLWwaV.zip (SHA1 Hash: 2a4062e10a5de813f5688221dbeb3f3ff33eb417 ) - File hash - Malware

IZJQCAOXQb.zip (SHA1 Hash: eaec1754a69c50eac99e774b07ef156a1ca6de06 ) - File hash - Likely malware

MITRE ATT&CK Mapping

ATT&CK Technique - Technique ID

Multi-Stage Channels - T1104

BITS Jobs - T1197

Application Layer Protocol: Web Protocols - T1071.001

Acquire Infrastructure: Web Services - T1583.006

Obtain Capabilities: Malware - T1588.001

Masquerading - T1036

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
Roberto Romeu
Senior SOC Analyst

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May 6, 2026

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

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Software supply-chain attacks in 2026

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

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

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

1. Why the Axios Compromise Scaled

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

The attack chain was simple yet effective:

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

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

A view from Darktrace

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

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

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

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

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

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

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

2. Why Trivy bypassed security tooling trust

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

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

This was a coordinated multi‑phase attack:

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

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

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

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

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

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

Quest KACE: Legacy Risk, Real Impact

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

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

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

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

The strategic pattern: Ecosystem‑scale adversaries

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

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

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

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

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

Edited by Ryan Traill (Content Manager)

Appendices

References:

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

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

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

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

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

IoCs

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

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

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

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

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

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

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

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

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

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

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

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

- e1ec76a0e1f48901566d53828c34b5dc – MD5 - Possible Quest KACE exploitation payload

- d3beab2e2252a13d5689e9911c2b2b2fc3a41086 – SHA1 - Possible Quest KACE exploitation payload

- ab6677fcbbb1ff4a22cc3e7355e1c36768ba30bbf5cce36f4ec7ae99f850e6c5 – SHA256 - Possible Quest KACE exploitation payload

- 83b7a106a5e810a1781e62b278909396 – MD5 - Possible Quest KACE exploitation payload

- deb4b5841eea43cb8c5777ee33ee09bf294a670d – SHA1 - Possible Quest KACE exploitation payload

- b1b2f1e36dcaa36bc587fda1ddc3cbb8e04c3df5f1e3f1341c9d2ec0b0b0ffaf – SHA256 - Possible Quest KACE exploitation payload

Darktrace Model Detections

Anomalous Connection / Application Protocol on Uncommon Port

Anomalous Server Activity / Outgoing from Server

Anomalous Connection / New User Agent to IP Without Hostname

Anomalous File / EXE from Rare External Location

Anomalous File / Script from Rare External Location

Anomalous Server Activity / New User Agent from Internet Facing System

Anomalous Server Activity / Rare External from Server

Antigena / Network / External Threat / Antigena Suspicious File Block

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

Device / New User Agent

Device / Internet Facing Device with High Priority Alert

Anomalous File / New User Agent Followed By Numeric File Download

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

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May 6, 2026

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

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What are email-delivered prompt injection attacks?

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

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

Recent examples of prompt injection attacks

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

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

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

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

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

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

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

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

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

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

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

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

How does Darktrace catch these types of attacks?

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

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

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

Ask your email provider about email-delivered AI prompt injection

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

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

Questions to ask your email security provider

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

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

Learn more about securing AI in your enterprise.

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About the author
Kiri Addison
Senior Director of Product
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