Blog
/
Email
/
May 20, 2024

Don’t Take the Bait: How Darktrace Keeps Microsoft Teams Phishing Attacks at Bay

In this blog we examine how Darktrace was able to detect and block malicious phishing emails sent via Microsoft Teams that were impersonating an international hotel chain.
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
Min Kim
Cyber Security Analyst
Default blog imageDefault blog imageDefault blog imageDefault blog imageDefault blog imageDefault blog image
20
May 2024

Social Engineering in Phishing Attacks

Faced with increasingly cyber-aware endpoint users and vigilant security teams, more and more threat actors are forced to think psychologically about the individuals they are targeting with their phishing attacks. Social engineering methods like taking advantage of the human emotions of their would-be victims, pressuring them to open emails or follow links or face financial or legal repercussions, and impersonating known and trusted brands or services, have become common place in phishing campaigns in recent years.

Phishing with Microsoft Teams

The malicious use of the popular communications platform Microsoft Teams has become widely observed and discussed across the threat landscape, with many organizations adopting it as their primary means of business communication, and many threat actors using it as an attack vector. As Teams allows users to communicate with people outside of their organization by default [1], it becomes an easy entry point for potential attackers to use as a social engineering vector.

In early 2024, Darktrace/Apps™ identified two separate instances of malicious actors using Microsoft Teams to launch a phishing attack against Darktrace customers in the Europe, the Middle East and Africa (EMEA) region. Interestingly, in this case the attackers not only used a well-known legitimate service to carry out their phishing campaign, but they were also attempting to impersonate an international hotel chain.

Despite these attempts to evade endpoint users and traditional security measures, Darktrace’s anomaly detection enabled it to identify the suspicious phishing messages and bring them to the customer’s attention. Additionally, Darktrace’s autonomous response capability, was able to follow-up these detections with targeted actions to contain the suspicious activity in the first instance.

Darktrace Coverage of Microsoft Teams Phishing

Chats Sent by External User and Following Actions by Darktrace

On February 29, 2024, Darktrace detected the presence of a new external user on the Software-as-a-Service (SaaS) environment of an EMEA customer for the first time. The user, “REDACTED@InternationalHotelChain[.]onmicrosoft[.]com” was only observed on this date and no further activities were detected from this user after February 29.

Later the same day, the unusual external user created its first chat on Microsoft Teams named “New Employee Loyalty Program”. Over the course of around 5 minutes, the user sent 63 messages across 21 different chats to unique internal users on the customer’s SaaS platform. All these chats included the ‘foreign tenant user’ and one of the customer’s internal users, likely in an attempt to remain undetected. Foreign tenant user, in this case, refers to users without access to typical internal software and privileges, indicating the presence of an external user.

Darktrace’s detection of unusual messages being sent by a suspicious external user via Microsoft Teams.
Figure 1: Darktrace’s detection of unusual messages being sent by a suspicious external user via Microsoft Teams.
Advanced Search results showing the presence of a foreign tenant user on the customer’s SaaS environment.
Figure 2: Advanced Search results showing the presence of a foreign tenant user on the customer’s SaaS environment.

Darktrace identified that the external user had connected from an unusual IP address located in Poland, 195.242.125[.]186. Darktrace understood that this was unexpected behavior for this user who had only previously been observed connecting from the United Kingdom; it further recognized that no other users within the customer’s environment had connected from this external source, thereby deeming it suspicious. Further investigation by Darktrace’s analyst team revealed that the endpoint had been flagged as malicious by several open-source intelligence (OSINT) vendors.

External Summary highlighting the rarity of the rare external source from which the Teams messages were sent.
Figure 3: External Summary highlighting the rarity of the rare external source from which the Teams messages were sent.

Following Darktrace’s initial detection of these suspicious Microsoft Teams messages, Darktrace's autonomous response was able to further support the customer by providing suggested mitigative actions that could be applied to stop the external user from sending any additional phishing messages.

Unfortunately, at the time of this attack Darktrace's autonomous response capability was configured in human confirmation mode, meaning any autonomous response actions had to be manually actioned by the customer. Had it been enabled in autonomous response mode, it would have been able promptly disrupt the attack, disabling the external user to prevent them from continuing their phishing attempts and securing precious time for the customer’s security team to begin their own remediation procedures.

Darktrace autonomous response actions that were suggested following the ’Large Volume of Messages Sent from New External User’ detection model alert.
Figure 4: Darktrace autonomous response actions that were suggested following the ’Large Volume of Messages Sent from New External User’ detection model alert.

External URL Sent within Teams Chats

Within the 21 Teams chats created by the threat actor, Darktrace identified 21 different external URLs being sent, all of which included the domain "cloud-sharcpoint[.]com”. Many of these URLs had been recently established and had been flagged as malicious by OSINT providers [3]. This was likely an attempt to impersonate “cloud-sharepoint[.]com”, the legitimate domain of Microsoft SharePoint, with the threat actor attempting to ‘typo-squat’ the URL to convince endpoint users to trust the legitimacy of the link. Typo-squatted domains are commonly misspelled URLs registered by opportunistic attackers in the hope of gaining the trust of unsuspecting targets. They are often used for nefarious purposes like dropping malicious files on devices or harvesting credentials.

Upon clicking this malicious link, users were directed to a similarly typo-squatted domain, “InternatlonalHotelChain[.]sharcpoInte-docs[.]com”. This domain was likely made to appear like the SharePoint URL used by the international hotel chain being impersonated.

Redirected link to a fake SharePoint page attempting to impersonate an international hotel chain.
Figure 5: Redirected link to a fake SharePoint page attempting to impersonate an international hotel chain.

This fake SharePoint page used the branding of the international hotel chain and contained a document named “New Employee Loyalty Program”; the same name given to the phishing messages sent by the attacker on Microsoft Teams. Upon accessing this file, users would be directed to a credential harvester, masquerading as a Microsoft login page, and prompted to enter their credentials. If successful, this would allow the attacker to gain unauthorized access to a user’s SaaS account, thereby compromising the account and enabling further escalation in the customer’s environment.

Figure 6: A fake Microsoft login page that popped-up when attempting to open the ’New Employee Loyalty Program’ document.

This is a clear example of an attacker attempting to leverage social engineering tactics to gain the trust of their targets and convince them to inadvertently compromise their account. Many corporate organizations partner with other companies and well-known brands to offer their employees loyalty programs as part of their employment benefits and perks. As such, it would not necessarily be unexpected for employees to receive such an offer from an international hotel chain. By impersonating an international hotel chain, threat actors would increase the probability of convincing their targets to trust and click their malicious messages and links, and unintentionally compromising their accounts.

In spite of the attacker’s attempts to impersonate reputable brands, platforms, Darktrace/Apps was able to successfully recognize the malicious intent behind this phishing campaign and suggest steps to contain the attack. Darktrace recognized that the user in question had deviated from its ‘learned’ pattern of behavior by connecting to the customer’s SaaS environment from an unusual external location, before proceeding to send an unusually large volume of messages via Teams, indicating that the SaaS account had been compromised.

A Wider Campaign?

Around a month later, in March 2024, Darktrace observed a similar incident of a malicious actor impersonating the same international hotel chain in a phishing attacking using Microsoft Teams, suggesting that this was part of a wider phishing campaign. Like the previous example, this customer was also based in the EMEA region.  

The attack tactics identified in this instance were very similar to the previously example, with a new external user identified within the network proceeding to create a series of Teams messages named “New Employee Loyalty Program” containing a typo-squatted external links.

There were a few differences with this second incident, however, with the attacker using the domain “@InternationalHotelChainExpeditions[.]onmicrosoft[.]com” to send their malicious Teams messages and using differently typo-squatted URLs to imitate Microsoft SharePoint.

As both customers targeted by this phishing campaign were subscribed to Darktrace’s Proactive Threat Notification (PTN) service, this suspicious SaaS activity was promptly escalated to the Darktrace Security Operations Center (SOC) for immediate triage and investigation. Following their investigation, the SOC team sent an alert to the customers informing them of the compromise and advising urgent follow-up.

Conclusion

While there are clear similarities between these Microsoft Teams-based phishing attacks, the attackers here have seemingly sought ways to refine their tactics, techniques, and procedures (TTPs), leveraging new connection locations and creating new malicious URLs in an effort to outmaneuver human security teams and conventional security tools.

As cyber threats grow increasingly sophisticated and evasive, it is crucial for organizations to employ intelligent security solutions that can see through social engineering techniques and pinpoint suspicious activity early.

Darktrace’s Self-Learning AI understands customer environments and is able to recognize the subtle deviations in a device’s behavioral pattern, enabling it to effectively identify suspicious activity even when attackers adapt their strategies. In this instance, this allowed Darktrace to detect the phishing messages, and the malicious links contained within them, despite the seemingly trustworthy source and use of a reputable platform like Microsoft Teams.

Credit to Min Kim, Cyber Security Analyst, Raymond Norbert, Cyber Security Analyst and Ryan Traill, Threat Content Lead

Appendix

Darktrace Model Detections

SaaS Model

Large Volume of Messages Sent from New External User

SaaS / Unusual Activity / Large Volume of Messages Sent from New External User

Indicators of Compromise (IoCs)

IoC – Type - Description

https://cloud-sharcpoint[.]com/[a-zA-Z0-9]{15} - Example hostname - Malicious phishing redirection link

InternatlonalHotelChain[.]sharcpolnte-docs[.]com – Hostname – Redirected Link

195.242.125[.]186 - External Source IP Address – Malicious Endpoint

MITRE Tactics

Tactic – Technique

Phishing – Initial Access (T1566)

References

[1] https://learn.microsoft.com/en-us/microsoftteams/trusted-organizations-external-meetings-chat?tabs=organization-settings

[2] https://www.virustotal.com/gui/ip-address/195.242.125.186/detection

[3] https://www.virustotal.com/gui/domain/cloud-sharcpoint.com

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
Min Kim
Cyber Security Analyst

More in this series

No items found.

Blog

/

Network

/

May 5, 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

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

Blog

/

Email

/

May 5, 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.

Continue reading
About the author
Kiri Addison
Senior Director of Product
Your data. Our AI.
Elevate your network security with Darktrace AI