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July 9, 2024

How Darktrace Detects NTLM Hash Theft

Explore Darktrace's innovative methods for detecting NTLM hash theft and safeguarding your organization from 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
Charlotte Thompson
Cyber Analyst
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09
Jul 2024

What is credential theft and how does it work?

What began as a method to achieve unauthorized access to an account, often driven by the curiosity of individual attackers, credentials theft become a key tactic for malicious actors and groups, as stolen login credentials can be abused to gain unauthorized access to accounts and systems. This access can be leveraged to carry out malicious activities such as data exfiltration, fraud, espionage and malware deployment.

It is therefore no surprise that the number of dark web marketplaces selling privileged credentials has increased in recent years, making it easier for malicious actors to monetize stolen credentials [1]. This, in turn, has created new opportunities for threat actors to use increasingly sophisticated tactics such as phishing, social engineering and credential stuffing in their attacks, targeting individuals, organizations and government entities alike [1].

Credential theft example

TA577 Threat Actor

TA577 is a threat actor known to leverage stolen credentials, also known as Hive0118 [2], an initial access broker (IAB) group that was previously known for delivering malicious payloads [2]. On March 4, 2024, Proofpoint reported evidence of TA577 using a new attack chain with a different aim in mind: stealing NT LAN Manager (NTLM) hashes that can be used to authenticate to systems without needing to know plaintext passwords [3].

How does TA577 steal credentials?

Proofpoint reported that this new attack chain, which was first observed on February 26 and 27, was made up of two distinct campaigns. The first campaign consisted of a phishing attack featuring tens of thousands of emails targeting hundreds of organizations globally [3]. These phishing emails often appeared as replies to previous messages (thread hijacking) and contained zipped HTML attachments that each contained a unique file hash, customized for each recipient [3]. These attached files also contained a HTTP Meta refresh function, which triggered an automatic connection to a text file hosted on external IP addresses running as SMB servers [3].

When attempting to access the text file, the server requires an SMB session authentication via NTLM. This session is initiated when a client sends an ‘SMB_COM_NEGOTIATE’ request to the server, which answers with a ‘SMB_COM_NEGOTIATE’ response.

The client then proceeds to send a ‘SMB_COM_SESSION_SETUP_ANDX’ request to start the SMB session setup process, which includes initiating the NTLM authentication process. The server responds with an ‘SMB_COM_SESSION_SETUP_ANDX’ response, which includes an NTLM challenge message [6].

The client can then use the challenge message and its own credentials to generate a response by hashing its password using an NTLM hash algorithm. The response is sent to the server in an ‘SMB_COM_SESSION_SETUP_ANDX’ request. The server validates the response and, if the authentication is successful, the server answers with a final ‘SMB_COM_SESSION_SETUP_ANDX’ response, which completes the session setup process and allows the client to access the file listed on the server [6].

What is the goal of threat actor TA577?

As no malware delivery was detected during these sessions, researchers have suggested that the aim of TA577 was not to deliver malware, but rather to take advantage of the NTLMV2 challenge/response to steal NTLM authentication hashes [3] [4]. Hashes stolen by attackers can be exploited in pass-the-hash attacks to authenticate to a remote server or service [4]. They can also be used for offline password cracking which, if successful, could be utilized to escalate privileges or perform lateral movement through a target network [4]. Under certain circumstances, these hashes could also permit malicious actors to hijack accounts, access sensitive information and evade security products [4].

The open-source toolkit Impacket, which includes modules for password cracking [5] and which can be identified by the default NTLM server challenge “aaaaaaaaaaaaaaaa”[3], was observed during the SMB sessions. This indicates that TA577 actor aim to use stolen credentials for password cracking and pass-the-hash attacks.

TA577 has previously been associated with Black Basta ransomware infections and Qbot, and has been observed delivering various payloads including IcedID, SystemBC, SmokeLoader, Ursnif, and Cobalt Strike [2].This change in tactic to follow the current trend of credential theft may indicate that not only are TA577 actors aware of which methods are most effective in the current threat landscape, but they also have monetary and time resources needed to create new methods to bypass existing detection tools [3].  

Darktrace’s Coverage of TA577 Activity

On February 26 and 27, coinciding with the campaign activity reported by Proofpoint, Darktrace/Email™ observed a surge of inbound emails from numerous suspicious domains targeting multiple customer environments. These emails consistently included zip files with seemingly randomly generated names, containing HTLM content and links to an unusual external IP address [3].

A summary of anomaly indicators seen for a campaign email sent by TA577, as detected by Darktrace/Email.
Figure 1: A summary of anomaly indicators seen for a campaign email sent by TA577, as detected by Darktrace/Email.
Details of the name and size of the .zip file attached to a campaign email, along with the Darktrace/Email model alerts triggered by the email.
Figure 2: Details of the name and size of the .zip file attached to a campaign email, along with the Darktrace/Email model alerts triggered by the email.

The URL of these links contained an unusually named .txt file, which corresponds with Proofpoint reports of the automatic connection to a text file hosted on an external SMB server made when the attachment is opened [3].

A link to a rare external IP address seen within a campaign email, containing an unusually named .txt file.
Figure 3: A link to a rare external IP address seen within a campaign email, containing an unusually named .txt file.

Darktrace identified devices on multiple customer networks connecting to external SMB servers via the SMB protocol. It understood this activity was suspicious as the SMB protocol is typically reserved for internal connections and the endpoint in question had never previously been observed on the network.

The Event Log of a ‘Compliance / External Windows Communication’ model alert showing a connection to an external SMB server on destination port 445.
Figure 4: The Event Log of a ‘Compliance / External Windows Communication’ model alert showing a connection to an external SMB server on destination port 445.
External Sites Summary highlighting the rarity of the external SMB server.
Figure 5: External Sites Summary highlighting the rarity of the external SMB server.
External Sites Summary highlightin that the SMB server is geolocated in Moldova.
Figure 6: External Sites Summary highlightin that the SMB server is geolocated in Moldova.

During these connections, Darktrace observed multiple devices establishing an SMB session to this server via a NTLM challenge/response, representing the potential theft of the credentials used in this session. During this session, some devices also attempted to access an unusually named .txt file, further indicating that the affected devices were trying to access the .txt file hosted on external SMB servers [3].

Packet captures (PCAPs) of these sessions show the default NTLM server challenge, indicating the use of Impacket, suggesting that the captured NTLM hashes were to be used for password cracking or pass-the-hash-attacks [3]

PCAP analysis showing usage of the default NTLM server challenge associated with Impacket.
Figure 7: PCAP analysis showing usage of the default NTLM server challenge associated with Impacket.

Conclusions

Ultimately, Darktrace’s suite of products effectively detected and alerted for multiple aspects of the TA577 attack chain and NTLM hash data theft activity across its customer base. Darktrace/Email was able to uncover the inbound phishing emails that served as the initial access vector for TA577 actors, while Darktrace DETECT identified the subsequent external connections to unusual external locations and suspicious SMB sessions.

Furthermore, Darktrace’s anomaly-based approach enabled it to detect suspicious TA577 activity across the customer base on February 26 and 27, prior to Proofpoint’s report on their new attack chain. This showcases Darktrace’s ability to identify emerging threats based on the subtle deviations in a compromised device’s behavior, rather than relying on a static list of indicators of compromise (IoCs) or ‘known bads’.

This approach allows Darktrace to remain one step ahead of increasingly adaptive threat actors, providing organizations and their security teams with a robust AI-driven solution able to safeguard their networks in an ever-evolving threat landscape.

Credit to Charlotte Thompson, Cyber Analyst, Anna Gilbertson, Cyber Analyst.

References

1)    https://www.sentinelone.com/cybersecurity-101/what-is-credential-theft/

2)    https://malpedia.caad.fkie.fraunhofer.de/actor/ta577

3)    https://www.proofpoint.com/us/blog/threat-insight/ta577s-unusual-attack-chain-leads-ntlm-data-theft

4)    https://www.bleepingcomputer.com/news/security/hackers-steal-windows-ntlm-authentication-hashes-in-phishing-attacks/

5)    https://pawanjswal.medium.com/the-power-of-impacket-a-comprehensive-guide-with-examples-1288f3a4c674

6)    https://learn.microsoft.com/en-us/openspecs/windows_protocols/ms-nlmp/c083583f-1a8f-4afe-a742-6ee08ffeb8cf

7)    https://www.hivepro.com/threat-advisory/ta577-targeting-windows-ntlm-hashes-in-global-campaigns/

Darktrace Model Detections

Darktrace/Email

·       Attachment / Unsolicited Archive File

·       Attachment / Unsolicited Attachment

·       Link / New Correspondent Classified Link

·       Link / New Correspondent Rare Link

·       Spoof / Internal User Similarities

Darktrace DETECT

·       Compliance / External Windows Communications

Darktrace RESPOND

·       Antigena / Network / Significant Anomaly / Antigena Breaches Over Time Block

IoCs

IoC - Type - Description

176.123.2[.]146 - IP address -Likely malicious SMB Server

89.117.2[.]33 - IP address - Likely malicious SMB Server

89.117.1[.]161 - IP address - Likely malicious SMB Server

104.129.20[.]167 - IP address - Likely malicious SMB Server

89.117.1[.]160 - IP address - Likely malicious SMB Server

85.239.33[.]149 - IP address - Likely malicious SMB Server

89.117.2[.]34 - IP address - Likely malicious SMB Server

146.19.213[.]36 - IP address - Likely malicious SMB Server

66.63.188[.]19 - IP address - Likely malicious SMB Server

103.124.104[.]76 - IP address - Likely malicious SMB Server

103.124.106[.]224 - IP address - Likely malicious SMB Server

\5aohv\9mn.txt - SMB Path and File - SMB Path and File

\hvwsuw\udrh.txt - SMB Path and File - SMB Path and File

\zkf2rj4\VmD.txt = SMB Path and File - SMB Path and File

\naams\p3aV.txt - SMB Path and File - SMB Path and File

\epxq\A.txt - SMB Path and File - SMB Path and File

\dbna\H.txt - SMB Path and File - SMB Path and File

MAGNAMSB.zip – Filename - Phishing Attachment

e751f9dddd24f7656459e1e3a13307bd03ae4e67 - SHA1 Hash - Phishing Attachment

OMNIS2C.zip  - Filename - Phishing Attachment

db982783b97555232e28d5a333525118f10942e1 - SHA1 Hash - Phishing Attachment

aaaaaaaaaaaaaaaa - NTLM Server Challenge -Impacket Default NTLM Challenge

MITRE ATT&CK Tactics, Techniques and Procedures (TTPs)

Tactic - Technique

TA0001            Initial Access

TA0002            Execution

TA0008            Lateral Movement

TA0003            Persistence

TA0005            Defense Evasion

TA0006            Credential Access

T1021.002       SMB/Windows Admin Shares

T1021  Remote Services

T1566.001       Spearfishing Attachment

T1566  Phishing

T1204.002       Malicious File

T1204  User Execution

T1021.002       SMB/Windows Admin Shares

T1574  Hijack Execution Flow

T1021  Remote Services

T1555.004       Windows Credential Manager

T1555  Credentials from Password Stores

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
Charlotte Thompson
Cyber Analyst

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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

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

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May 5, 2026

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

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What are email-delivered prompt injection attacks?

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

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

Recent examples of prompt injection attacks

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

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

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

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

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

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

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

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

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

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

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

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

How does Darktrace catch these types of attacks?

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

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

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

Ask your email provider about email-delivered AI prompt injection

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

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

Questions to ask your email security provider

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

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

Learn more about securing AI in your enterprise.

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About the author
Kiri Addison
Senior Director of Product
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