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August 14, 2025

From Exploit to Escalation: Tracking and Containing a Real-World Fortinet SSL-VPN Attack

This blog outlines a real-world attack where threat actors exploited Fortinet SSL-VPN vulnerabilities to infiltrate a network. It highlights how Darktrace identified threat and took immediate actions to contain it, demonstrating the importance of proactive detection and rapid intervention in minimizing risk and disruption.
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
Priya Thapa
Cyber Analyst
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14
Aug 2025

Threat actors exploiting Fortinet CVEs

Over the years, Fortinet has issued multiple alerts about a wave of sophisticated attacks targeting vulnerabilities in its SSL-VPN infrastructure. Despite the release of patches to address these vulnerabilities, threat actors have continued to exploit a trio of Common Vulnerabilities and Exposures (CVEs) disclosed between 2022 and 2024 to gain unauthorized access to FortiGate devices.

Which vulnerabilities are exploited?

The vulnerabilities—CVE-2022-42475, CVE-2023-27997, and CVE-2024-21762—affect Fortinet’s SSL-VPN services and have been actively exploited by threat actors to establish initial access into target networks.

The vulnerabilities affect core components of FortiOS, allowing attackers to execute remote code on affected systems.

CVE-2022-42475

Type: Heap-Based Buffer Overflow in FortiOS SSL-VPN

Impact: Remote Code Execution (Actively Exploited)

This earlier vulnerability also targets the SSL-VPN interface and has been actively exploited in the wild. It allows attackers to execute arbitrary code remotely by overflowing a buffer in memory, often used to deploy malware or establish persistent backdoors [6].

CVE-2023-27997

Type: Heap-Based Buffer Overflow in FortiOS and FortiProxy

Impact: Remote Code Execution

This flaw exists in the SSL-VPN component of both FortiOS and FortiProxy. By exploiting a buffer overflow in the heap memory, attackers can execute malicious code remotely. This vulnerability is particularly dangerous because it can be triggered without authentication, making it ideal for an initial compromise [5].

CVE-2024-21762

Type: Out-of-Bounds Write in sslvpnd

Impact: Remote Code Execution

This vulnerability affects the SSL-VPN daemon (sslvpnd) in FortiOS. It allows unauthenticated remote attackers to send specially crafted HTTP requests that write data outside of allocated memory bounds. This can lead to arbitrary code execution, giving attackers full control over a device [4].

In short, these flaws enable remote attackers to execute arbitrary code without authentication by exploiting memory corruption issues such as buffer overflows and out-of-bounds writes. Once inside, threat actors use symbolic link (symlink) in order to maintain persistence on target devices across patches and firmware updates. This persistence then enables them to bypass security controls and manipulate firewall configurations, effectively turning patched systems into long-term footholds for deeper network compromise [1][2][3].

Darktrace’s Coverage

Darktrace detected a series of suspicious activities originating from a compromised Fortinet VPN device, including anomalous HTTP traffic, internal network scanning, and SMB reconnaissance, all indicative of post-exploitation behavior. Following initial detection by Darktrace’s real-time models, its Autonomous Response capability swiftly acted on the malicious activity, blocking suspicious connections and containing the threat before further compromise could occur.

Further investigation by Darktrace’s Threat Research team uncovered a stealthy and persistent attack that leveraged known Fortinet SSL-VPN vulnerabilities to facilitate lateral movement and privilege escalation within the network.

Phase 1: Initial Compromise – Fortinet VPN Exploitation

The attack on a Darktrace customer likely began on April 11 with the exploitation of a Fortinet VPN device running an outdated version of FortiOS. Darktrace observed a high volume of HTTP traffic originating from this device, specifically targeting internal systems. Notably, many of these requests were directed at the /cgi-bin/ directory,  a common target for attackers attempting to exploit web interfaces to run unauthorized scripts or commands. This pattern strongly indicated remote code execution attempts via the SSL-VPN interface [7].

Once access was gained, the threat actor likely modified existing firewall rules, a tactic often used to disable security controls or create hidden backdoors for future access. While Darktrace does not have direct visibility into firewall configuration changes, the surrounding activity and post-exploitation behavior indicated that such modifications were made to support long-term persistence within the network.

HTTP activity from the compromised Fortinet device, including repeated requests to /cgi-bin/ over port 8080.
Figure 1: HTTP activity from the compromised Fortinet device, including repeated requests to /cgi-bin/ over port 8080

Phase 2: Establishing Persistence & Lateral Movement

Shortly after the initial compromise of the Fortinet VPN device, the threat actor began to expand their foothold within the internal network. Darktrace detected initial signs of network scanning from this device, including the use of Nmap to probe the internal environment, likely in an attempt to identify accessible services and vulnerable systems.

Darktrace’s detection of unusual network scanning activities on the affected device.
Figure 2: Darktrace’s detection of unusual network scanning activities on the affected device.

Around the same time, Darktrace began detecting anomalous activity on a second device, specifically an internal firewall interface device. This suggested that the attacker had established a secondary foothold and was leveraging it to conduct deeper reconnaissance and move laterally through the network.

In an effort to maintain persistence within the network, the attackers likely deployed symbolic links in the SSL-VPN language file directory on the Fortinet device. While Darktrace did not directly observe symbolic link abuse, Fortinet has identified this as a known persistence technique in similar attacks [2][3]. Based on the observed post-exploitation behavior and likely firewall modifications, it is plausible that such methods were used here.

Phase 3: Internal Reconnaissance & Credential Abuse

With lateral movement initiated from the internal firewall interface device, the threat actor proceeded to escalate their efforts to map the internal network and identify opportunities for privilege escalation.

Darktrace observed a successful NTLM authentication from the internal firewall interface to the domain controller over the outdated protocol SMBv1, using the account ‘anonymous’. This was immediately followed by a failed NTLM session connection using the hostname ‘nmap’, further indicating the use of Nmap for enumeration and brute-force attempts. Additional credential probes were also identified around the same time, including attempts using the credential ‘guest’.

Darktrace detection of a series of login attempts using various credentials, with a mix of successful and unsuccessful attempts.
Figure 3: Darktrace detection of a series of login attempts using various credentials, with a mix of successful and unsuccessful attempts.

The attacker then initiated DCE_RPC service enumeration, with over 300 requests to the Endpoint Mapper endpoint on the domain controller. This technique is commonly used to discover available services and their bindings, often as a precursor to privilege escalation or remote service manipulation.

Over the next few minutes, Darktrace detected more than 1,700 outbound connections from the internal firewall interface device to one of the customer’s subnets. These targeted common services such as FTP (port 21), SSH (22), Telnet (23), HTTP (80), and HTTPS (443). The threat actor also probed administrative and directory services, including ports 135, 137, 389, and 445, as well as remote access via RDP on port 3389.

Further signs of privilege escalation attempts were observed with the detection of over 300 Netlogon requests to the domain controller. Just over half of these connections were successful, indicating possible brute-force authentication attempts, credential testing, or the use of default or harvested credentials.

Netlogon and DCE-RPC activity from the affected device, showing repeated service bindings to epmapper and Netlogon, followed by successful and failed NetrServerAuthenticate3 attempts.
Figure 4: Netlogon and DCE-RPC activity from the affected device, showing repeated service bindings to epmapper and Netlogon, followed by successful and failed NetrServerAuthenticate3 attempts.

Phase 4: Privilege Escalation & Remote Access

A few minutes later, the attacker initiated an RDP session from the internal firewall interface device to an internal server. The session lasted over three hours, during which more than 1.5MB of data was uploaded and over 5MB was downloaded.

Notably, no RDP cookie was observed during this session, suggesting manual access, tool-less exploitation, or a deliberate attempt to evade detection. While RDP cookie entries were present on other occasions, none were linked to this specific session—reinforcing the likelihood of stealthy remote access.

Additionally, multiple entries during and after this session show SSL certificate validation failures on port 3389, indicating that the RDP connection may have been established using self-signed or invalid certificates, a common tactic in unauthorized or suspicious remote access scenarios.

Darktrace’s detection of an RDP session from the firewall interface device to the server, lasting over 3 hours.
Figure 5: Darktrace’s detection of an RDP session from the firewall interface device to the server, lasting over 3 hours.

Darktrace Autonomous Response

Throughout the course of this attack, Darktrace’s Autonomous Response capability was active on the customer’s network. This enabled Darktrace to autonomously intervene by blocking specific connections and ports associated with the suspicious activity, while also enforcing a pre-established “pattern of life” on affected devices to ensure they were able to continue their expected business activities while preventing any deviations from it. These actions were crucial in containing the threat and prevent further lateral movement from the compromised device.

Darktrace’s Autonomous Response targeted specific connections and restricted affected devices to their expected patterns of life.
Figure 6: Darktrace’s Autonomous Response targeted specific connections and restricted affected devices to their expected patterns of life.

Conclusion

This incident highlights the importance of important staying on top of patching and closely monitoring VPN infrastructure, especially for internet-facing systems like Fortinet devices. Despite available patches, attackers were still able to exploit known vulnerabilities to gain access, move laterally and maintain persistence within the customer’s network.

Attackers here demonstrated a high level of stealth and persistence. Not only did they gain access to the network and carry out network scans and lateral movement, but they also used techniques such as symbolic link abuse, credential probing, and RDP sessions without cookies to avoid detection.  Darktrace’s detection of the post-exploitation activity, combined with the swift action of its Autonomous Response technology, successfully blocked malicious connections and contained the attack before it could escalate

Credit to Priya Thapa (Cyber Analyst), Vivek Rajan (Cyber Analyst), and Ryan Traill (Analyst Content Lead)

Appendices

Real-time Detection Model Alerts

·      Device / Suspicious SMB Scanning Activity

·      Device / Anomalous Nmap Activity

·      Device / Network Scan

·      Device / RDP Scan

·      Device / ICMP Address Scan

Autonomous Response Model Alerts:  

·      Antigena / Network / Insider Threat / Antigena Network Scan Block

·       Antigena / Network / Significant Anomaly / Antigena Significant Anomaly from Client Block

MITRE ATT&CK Mapping

Initial Access – External Remote Services – T1133

Initial Access – Valid Accounts – T1078

Execution – Exploitation for Client Execution – T1203

Persistence – Account Manipulation – T1098

Persistence – Application Layer Protocol – T1071.001

Privilege Escalation – Exploitation for Privilege Escalation – T1068

Privilege Escalation – Valid Accounts – T1078

Defense Evasion – Masquerading – T1036

Credential Access – Brute Force – T1110

Discovery – Network Service Scanning – T1046

Discovery – Remote System Discovery – T1018

Lateral Movement – Remote Services – T1021

Lateral Movement – Software Deployment Tools – T1072

Collection – Data from Local System – T1005

Collection – Data Staging – T1074

Exfiltration – Exfiltration Over Alternative Protocol – T1048

References

[1]  https://www.tenable.com/blog/cve-2024-21762-critical-fortinet-fortios-out-of-bound-write-ssl-vpn-vulnerability

[2] https://thehackernews.com/2025/04/fortinet-warns-attackers-retain.html

[3] https://www.cisa.gov/news-events/alerts/2025/04/11/fortinet-releases-advisory-new-post-exploitation-technique-known-vulnerabilities

[4] https://www.fortiguard.com/psirt/FG-IR-24-015

[5] https://www.tenable.com/blog/cve-2023-27997-heap-based-buffer-overflow-in-fortinet-fortios-and-fortiproxy-ssl-vpn-xortigate

[6]  https://www.tenable.com/blog/cve-2022-42475-fortinet-patches-zero-day-in-fortios-ssl-vpns

[7] https://www.fortiguard.com/encyclopedia/ips/12475

The content provided in this blog is published by Darktrace for general informational purposes only and reflects our understanding of cybersecurity topics, trends, incidents, and developments at the time of publication. While we strive to ensure accuracy and relevance, the information is provided “as is” without any representations or warranties, express or implied. Darktrace makes no guarantees regarding the completeness, accuracy, reliability, or timeliness of any information presented and expressly disclaims all warranties.

Nothing in this blog constitutes legal, technical, or professional advice, and readers should consult qualified professionals before acting on any information contained herein. Any references to third-party organizations, technologies, threat actors, or incidents are for informational purposes only and do not imply affiliation, endorsement, or recommendation.

Darktrace, its affiliates, employees, or agents shall not be held liable for any loss, damage, or harm arising from the use of or reliance on the information in this blog.

The cybersecurity landscape evolves rapidly, and blog content may become outdated or superseded. We reserve the right to update, modify, or remove any content without notice.

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
Priya Thapa
Cyber Analyst

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May 6, 2026

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

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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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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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