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February 20, 2020

Lessons Learned from a Sodinokibi Ransomware Attack

Gain insights into a targeted Sodinokibi ransomware attack and learn how to better prepare your organization for potential 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
Max Heinemeyer
Global Field CISO
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20
Feb 2020

Introduction

Last week, Darktrace detected a targeted Sodinokibi ransomware attack during a 4-week trial with a mid-sized company.

This blog post will go through every stage of the attack lifecycle and detail the attacker’s techniques, tools and procedures used, and how Darktrace detected the attack.

The Sodinokibi group is an innovative threat-actor that is sometimes referred to as a ‘double-threat’, due to their ability to run targeted attacks using ransomware while simultaneously exfiltrating their victim’s data. This enables them to threaten to make the victim’s data publicly available if the ransom is not paid.

While Darktrace’s AI was able to identify the attack in real time as it was emerging, unfortunately the security team didn’t have eyes on the technology and was unable to action the alerts — nor was Antigena set in active mode, which would have slowed down and contained the threat instantaneously.

Timeline

The timeline below provides a rough overview of the major attack phases. Most of the attack took place over the course of a week, with the majority of activity distributed over the last three days.

Technical analysis

Darktrace detected two main devices being hit by the attack: an internet-facing RDP server (‘RDP server’) and a Domain Controller (‘DC’), that also acts as a SMB file server.

In previous attacks, Sodinokibi has used host-level encryption for ransomware activity where the encryption takes place on the compromised host itself — in contrast to network-level encryption where the bulk of the ransomware activity takes place over network protocols such as SMB.

Initial compromise

Over several days, the victim’s external-facing RDP server was receiving successful RDP connections from a rare external IP address located in Ukraine.

Shortly before the initial reconnaissance started, Darktrace saw another RDP connection coming into the RDP server with the same RDP account as seen before. This connection lasted for almost an hour.

It is highly likely that the RDP credential used in this attack had been compromised prior to the attack, either via common brute-force methods, credential stuffing attacks, or phishing.

Thanks to Darktrace’s Deep-Packet Inspection, we can clearly see the connection and all related information.

Suspicious RDP connection information:

Time: 2020-02-10 16:57:06 UTC
Source: 46.150.70[.]86 (Ukraine)
Destination: 192.168.X.X
Destination Port: 64347
Protocol: RDP
Cookie: [REDACTED]
Duration: 00h41m40s
Data out: 8.44 MB
Data in: 1.86 MB

Darktrace detects incoming RDP connections from IP addresses that usually do not connect to the organization.

Attack tools download

Approximately 45 minutes after the suspicious RDP connection from Ukraine, the RDP server connected to the popular file sharing platform, Megaupload, and downloaded close to 300MB from there.

Darktrace’s AI recognized that neither this server, nor its automatically detected peer group, nor, in fact, anyone else on the network commonly utilized Megaupload — and therefore instantly detected this as anomalous behavior, and flagged it as unusual.

As well as the full hostname and actual IP used for the download, Megaupload is 100% rare for this organization.

Later on, we will see over 40GB being uploaded to Megaupload. This initial download of 300MB however is likely additional tooling and C2 implants downloaded by the threat-actor into the victim’s environment.

Internal reconnaissance

Only 3 minutes after the download from Megaupload onto the RDP server, Darktrace alerted on the RDP server doing an anomalous network scan:

The RDP server scanned 9 other internal devices on the same subnet on 7 unique ports: 21, 80, 139, 445, 3389, 4899, 8080
 . Anybody with some offensive security know-how will recognize most of these ports as default ports one would scan for in a Windows environment for lateral movement. Since this RDP server does not usually conduct network scans, Darktrace again identified this activity as highly anomalous.

Later on, we see the threat-actor do more network scanning. They become bolder and use more generic scans — one of them showing that they are using Nmap with a default user agent:

Additional Command and Control traffic

While the initial Command and Control traffic was most likely using predominantly RDP, the threat-actor now wanted to establish more persistence and create more resilient channels for C2.

Shortly after concluding the initial network scans (ca. 19:17 on 10th February 2020), the RDP server starts communicating with unusual external services that are unique and unusual for the victim’s environment.

Communications to Reddcoin

Again, nobody else is using Reddcoin on the network. The combination of application protocol and external port is extremely unusual for the network as well.

The communications also went to the Reddcoin API, indicating the installation of a software agent rather than manual communications. This was detected as Reddcoin was not only rare for the network, but also ‘young’ — i.e. this particular external destination had never been seen to be contacted before on the network until 25 minutes before.

Communications to the Reddcoin API

Communications to Exceptionless[.]io

As we can see, the communications to exceptionalness[.]io were done in a beaconing manner, using a Let’s Encrypt certificate, being rare for the network and using an unusual JA3 client hash. All of this indicates the presence of new software on the device, shortly after the threat-actor downloaded their 300MB of tooling.

While most of the above network activity started directly after the threat-actor dropped their tooling on the RDP server, the exact purpose of interfacing with Reddcoin and Exceptionless is unclear. The attacker seems to favor off-the-shelf tooling (Megaupload, Nmap, …) so they might use these services for C2 or telemetry-gathering purposes.

This concluded most of the activity on February 10.

More Command and Control traffic

Why would an attacker do this? Surely using all this C2 at the same time is much noisier than just using 1 or 2 channels?

Another significant burst of activity was observed on February 12 and 13.

The RDP server started making a lot of highly anomalous and rare connections to external destinations. It is inconclusive if all of the below services, IPs, and domains were used for C2 purposes only, but they are linked with high-confidence to the attacker’s activities:

  • HTTP beaconing to vkmuz[.]net
  • Significant amount of Tor usage
  • RDP connections to 198-0-244-153-static.hfc.comcastbusiness[.]net over non-standard RDP port 29348
  • RDP connections to 92.119.160[.]60 using an administrative account (geo-located in Russia)
  • Continued connections to Megaupload
  • Continued SSL beaconing to Exceptionless[.]io
  • Continued connections to api.reddcoin[.]com
  • SSL beaconing to freevpn[.]zone
  • HTTP beaconing to 31.41.116[.]201 to /index.php using a new User Agent
  • Unusual SSL connections to aj1713[.]online
  • Connections to Pastebin
  • SSL beaconing to www.itjx3no[.]com using an unusual JA3 client hash
  • SSL beaconing to safe-proxy[.]com
  • SSL connection to westchange[.]top without prior DNS hostname lookups (likely machine-driven)

What is significant here is the diversity in (potential) C2 channels: Tor, RDP going to dynamic ISP addresses, VPN solutions and possibly custom / customized off-the-shelf implants (the DGA-looking domains and HTTP to IP addresses to /index.php).

Why would an attacker do this? Surely using all this C2 at the same time is much noisier than just using 1 or 2 channels?

One answer might be that the attacker cared much more about short-term resilience than about stealth. As the overall attack in the network took less than 7 days, with a majority of the activity taking place over 2.5 days, this makes sense. Another possibility might be that various individuals were involved in parallel during this attack — maybe one attacker prefers the comfort of RDP sessions for hacking while another is more skilled and uses a particular post-exploitation framework.

The overall modus operandi in this financially-motivated attack is much more smash-and-grab than in the stealthy, espionage-related incidents observed in Advanced Persistent Threat campaigns (APT).

Data exfiltration

The DC uploaded around 40GB of data to Megaupload over the course of 24 hours.

While all of the above activity was seen on the RDP server (acting as the initial beach-head), the following data exfiltration activity was observed on a Domain Controller (DC) on the same subnet as the RDP server.

The DC uploaded around 40GB of data to Megaupload over the course of 24 hours.

Darktrace detected this data exfiltration while it was in progress — never did the DC (or any similar devices) upload similar amounts of data to the internet. Neither did any client nor server in the victim’s environment use Megaupload:

Ransom notes

Finally, Darktrace observed unusual files being accessed on internal SMB shares on February 13. These files appear to be ransom notes — they follow a similar, randomly-generated naming convention as other victims of the Sodinokibi group have reported:

413x0h8l-readme.txt
4omxa93-readme.txt

Conclusion and observations

The threat-actor seems to be using mostly off-the-shelf tooling which makes attribution harder — while also making detection more difficult.

This attack is representative of many of the current ransomware attacks: financially motivated, fast-acting, and targeted.

The threat-actor seems to be using mostly off-the-shelf tooling (RDP, Nmap, Mega, VPN solutions) which makes attribution harder — while also making detection more difficult. Using this kind of tooling often allows to blend in with regular admin activity — only once anomaly detection is used can this kind of activity be detected.

How can you spot the one anomalous outbound RDP connection amongst the thousands of regular RDP connections leaving your environment? How do you know when the use of Megaupload is malicious — compared to your users’ normal use of it? This is where the power of Darktrace’s self-learning AI comes into play.

Darktrace detected every stage of the visible attack lifecycle without using any threat intelligence or any static signatures.

The graphics below show an overview of detections on both compromised devices. The compromised devices were the highest-scoring assets for the network — even a level 1 analyst with limited previous exposure to Darktrace could detect such an in-progress attack in real time.

RDP Server

Some of the detections on the RDP server include:

  • Compliance / File Storage / Mega — using Megaupload in an unusual way
  • Device / Network Scan — detecting unusual network scans
  • Anomalous Connection / Application Protocol on Uncommon Port — detecting the use of protocols on unusual ports
  • Device / New Failed External Connections — detecting unusual failing C2
  • Compromise / Unusual Connections to Let’s Encrypt — detecting potential C2 over SSL using Let’s Encrypt
  • Compromise / Beacon to Young Endpoint — detecting C2 to new external endpoints for the network
  • Device / Attack and Recon Tools — detecting known offensive security tools like Nmap
  • Compromise / Tor Usage — detecting unusual Tor usage
  • Compromise / SSL Beaconing to Rare Destination — detecting generic SSL C2
  • Compromise / HTTP Beaconing to Rare Destination — detecting generic HTTP C2
  • Device / Long Agent Connection to New Endpoint — detecting unusual services on a device
  • Anomalous Connection / Outbound RDP to Unusual Port — detecting unusual RDP C2

DC

Some of the detections on the DC include:

  • Anomalous Activity / Anomalous External Activity from Critical Device — detecting unusual behaviour on dcs
  • Compliance / File storage / Mega — using Megaupload in an unusual way
  • Anomalous Connection / Data Sent to New External Device — data exfiltration to unusual locations
  • Anomalous Connection / Uncommon 1GB Outbound — large amounts of data leaving to unusual destinations
  • Anomalous Server Activity / Outgoing from Server — likely C2 to unusual endpoint on the internet


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
Max Heinemeyer
Global Field CISO

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May 6, 2026

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

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Software supply-chain attacks in 2026

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

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

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

1. Why the Axios Compromise Scaled

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

The attack chain was simple yet effective:

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

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

A view from Darktrace

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

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

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

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

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

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

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

2. Why Trivy bypassed security tooling trust

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

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

This was a coordinated multi‑phase attack:

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

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

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

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

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

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

Quest KACE: Legacy Risk, Real Impact

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

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

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

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

The strategic pattern: Ecosystem‑scale adversaries

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

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

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

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

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

Edited by Ryan Traill (Content Manager)

Appendices

References:

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

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

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

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

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

IoCs

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

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

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

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

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

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

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

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

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

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

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

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

- e1ec76a0e1f48901566d53828c34b5dc – MD5 - Possible Quest KACE exploitation payload

- d3beab2e2252a13d5689e9911c2b2b2fc3a41086 – SHA1 - Possible Quest KACE exploitation payload

- ab6677fcbbb1ff4a22cc3e7355e1c36768ba30bbf5cce36f4ec7ae99f850e6c5 – SHA256 - Possible Quest KACE exploitation payload

- 83b7a106a5e810a1781e62b278909396 – MD5 - Possible Quest KACE exploitation payload

- deb4b5841eea43cb8c5777ee33ee09bf294a670d – SHA1 - Possible Quest KACE exploitation payload

- b1b2f1e36dcaa36bc587fda1ddc3cbb8e04c3df5f1e3f1341c9d2ec0b0b0ffaf – SHA256 - Possible Quest KACE exploitation payload

Darktrace Model Detections

Anomalous Connection / Application Protocol on Uncommon Port

Anomalous Server Activity / Outgoing from Server

Anomalous Connection / New User Agent to IP Without Hostname

Anomalous File / EXE from Rare External Location

Anomalous File / Script from Rare External Location

Anomalous Server Activity / New User Agent from Internet Facing System

Anomalous Server Activity / Rare External from Server

Antigena / Network / External Threat / Antigena Suspicious File Block

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

Device / New User Agent

Device / Internet Facing Device with High Priority Alert

Anomalous File / New User Agent Followed By Numeric File Download

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

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May 6, 2026

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

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What are email-delivered prompt injection attacks?

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

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

Recent examples of prompt injection attacks

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

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

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

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

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

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

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

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

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

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

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

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

How does Darktrace catch these types of attacks?

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

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

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

Ask your email provider about email-delivered AI prompt injection

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

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

Questions to ask your email security provider

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

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

Learn more about securing AI in your enterprise.

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