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October 26, 2022

Strategies to Prolong Quantum Ransomware Attacks

Learn more about how Darktrace combats Quantum Ransomware changing strategy for cyberattacks. Explore the power of AI-driven network cyber security!
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
Nicole Wong
Cyber Security Analyst
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26
Oct 2022

Within science and engineering, the word ‘quantum’ may spark associations with speed and capability, referencing a superior computer that can perform tasks a classical computer cannot. In cyber security, some may recognize ‘quantum’ in relation to cryptography or, more recently, as the name of a new ransomware group, which achieved network-wide encryption a mere four hours after an initial infection.   

Although this group now has a reputation for carrying out fast and efficient attacks, speed is not their only tactic. In August 2022, Darktrace detected a Quantum Ransomware incident where attackers remained in the victim’s network for almost a month after the initial signs of infection, before detonating ransomware. This was a stark difference to previously reported attacks, demonstrating that as motives change, so do threat actors’ strategies. 

The Quantum Group

Quantum was first identified in August 2021 as the latest of several rebrands of MountLocker ransomware [1]. As part of this rebrand, the extension ‘.quantum’ is appended to filenames that are encrypted and the associated ransom notes are named ‘README_TO_DECRYPT.html’ [2].  

From April 2022, media coverage of this group has increased following a DFIR report detailing an attack that progressed from initial access to domain-wide ransomware within four hours [3]. To put this into perspective, the global median dwell time for ransomware in 2020 and 2021 is 5 days [4]. In the case of Quantum, threat actors gained direct keyboard access to devices merely 2 hours after initial infection. The ransomware was staged on the domain controller around an hour and a half later, and executed 12 minutes after that.   

Quantum’s behaviour bears similarities to other groups, possibly due to their history and recruitment. Several members of the disbanded Conti ransomware group are reported to have joined the Quantum and BumbleBee operations. Security researchers have also identified similarities in the payloads and C2 infrastructure used by these groups [5 & 6].  Notably, these are the IcedID initial payload and Cobalt Strike C2 beacon used in this attack. Darktrace has also observed and prevented IcedID and Cobalt Strike activity from BumbleBee across several customer environments.

The Attack

From 11th July 2022, a device suspected to be patient zero made repeated DNS queries for external hosts that appear to be associated with IcedID C2 traffic [7 & 8]. In several reported cases [9 & 10], this banking trojan is delivered through a phishing email containing a malicious attachment that loads an IcedID DLL. As Darktrace was not deployed in the prospect’s email environment, there was no visibility of the initial access vector, however an example of a phishing campaign containing this payload is presented below. It is also possible that the device was already infected prior to joining the network. 

Figure 1- An example phishing email used to distribute IcedID. If configured, Darktrace/Email would be able to detect that the email was sent from an anomalous sender, was part of a fake reply chain, and had a suspicious attachment containing compressed content of unusual mime type [11].    

 

Figure 2- The DNS queries to endpoints associated with IcedID C2 servers, taken from the infected device’s event log.  Additional DNS queries made to other IcedID C2 servers are in the list of IOCs in the appendices.  The repeated DNS queries are indicative of beaconing.


It was not until 22nd July that activity was seen which indicated the attack had progressed to the next stage of the kill chain. This contrasts the previously seen attacks where the progression to Cobalt Strike C2 beaconing and reconnaissance and lateral movement occurred within 2 hours of the initial infection [12 & 13]. In this case, patient zero initiated numerous unusual connections to other internal devices using a compromised account, connections that were indicative of reconnaissance using built-in Windows utilities:

·      DNS queries for hostnames in the network

·      SMB writes to IPC$ shares of those hostnames queried, binding to the srvsvc named pipe to enumerate things such as SMB shares and services on a device, client access permissions on network shares and users logged in to a remote session

·      DCE-RPC connections to the endpoint mapper service, which enables identification of the ports assigned to a particular RPC service

These connections were initiated using an existing credential on the device and just like the dwelling time, differed from previously reported Quantum group attacks where discovery actions were spawned and performed automatically by the IcedID process [14]. Figure 3 depicts how Darktrace detected that this activity deviated from the device’s normal behaviour.  

Figure 3- This figure displays the spike in active internal connections initiated by patient zero. The coloured dots represent the Darktrace models that were breached, detecting this unusual reconnaissance and lateral movement activity.

Four days later, on the 26th of July, patient zero performed SMB writes of DLL and MSI executables to the C$ shares of internal devices including domain controllers, using a privileged credential not previously seen on the patient zero device. The deviation from normal behaviour that this represents is also displayed in Figure 3. Throughout this activity, patient zero made DNS queries for the external Cobalt Strike C2 server shown in Figure 4. Cobalt Strike has often been seen as a secondary payload delivered via IcedID, due to IcedID’s ability to evade detection and deploy large scale campaigns [15]. It is likely that reconnaissance and lateral movement was performed under instructions received by the Cobalt Strike C2 server.   

Figure 4- This figure is taken from Darktrace’s Advanced Search interface, showing a DNS query for a Cobalt Strike C2 server occurring during SMB writes of .dll files and DCE-RPC requests to the epmapper service, demonstrating reconnaissance and lateral movement.


The SMB writes to domain controllers and usage of a new account suggests that by this stage, the attacker had achieved domain dominance. The attacker also appeared to have had hands-on access to the network via a console; the repetition of the paths ‘programdata\v1.dll’ and ‘ProgramData\v1.dll’, in lower and title case respectively, suggests they were entered manually.  

These DLL files likely contained a copy of the malware that injects into legitimate processes such as winlogon, to perform commands that call out to C2 servers [16]. Shortly after the file transfers, the affected domain controllers were also seen beaconing to external endpoints (‘sezijiru[.]com’ and ‘gedabuyisi[.]com’) that OSINT tools have associated with these DLL files [17 & 18]. Moreover, these SSL connections were made using a default client fingerprint for Cobalt Strike [19], which is consistent with the initial delivery method. To illustrate the beaconing nature of these connections, Figure 5 displays the 4.3 million daily SSL connections to one of the C2 servers during the attack. The 100,000 most recent connections were initiated by 11 unique source IP addresses alone.

Figure 5- The Advanced Search interface, querying for external SSL connections from devices in the network to an external host that appears to be a Cobalt Strike C2 server. 4.3 million connections were made over 8 days, even after the ransomware was eventually detonated on 2022-08-03.


Shortly after the writes, the attack progressed to the penultimate stage. The next day, on the 27th of July, the attackers moved to achieve their first objective: data exfiltration. Data exfiltration is not always performed by the Quantum ransomware gang. Researchers have noted discrepancies between claims of data theft made in their ransom notes versus the lack of data seen leaving the network, although this may have been missed due to covert exfiltration via a Cobalt Strike beacon [20]. 

In contrast, this attack displayed several gigabytes of data leaving internal devices including servers that had previously beaconed to Cobalt Strike C2 servers. This data was transferred overtly via FTP, however the attacker still attempted to conceal the activity using ephemeral ports (FTP in EPSV mode). FTP is an effective method for attackers to exfiltrate large files as it is easy to use, organizations often neglect to monitor outbound usage, and it can be shipped through ports that will not be blocked by traditional firewalls [21].   

Figure 6 displays an example of the FTP data transfer to attacker-controlled infrastructure, in which the destination share appears structured to identify the organization that the data was stolen from, suggesting there may be other victim organizations’ data stored. This suggests that data exfiltration was an intended outcome of this attack. 

Figure 6- This figure is from Darktrace’s Advanced Search interface, displaying some of the data transferred from an internal device to the attacker’s FTP server.

 
Data was continuously exfiltrated until a week later when the final stage of the attack was achieved and Quantum ransomware was detonated. Darktrace detected the following unusual SMB activity initiated from the attacker-created account that is a hallmark for ransomware (see Figure 7 for example log):

·      Symmetric SMB Read to Write ratio, indicative of active encryption

·      Sustained MIME type conversion of files, with the extension ‘.quantum’ appended to filenames

·      SMB writes of a ransom note ‘README_TO_DECRYPT.html’ (see Figure 8 for an example note)

Figure 7- The Model Breach Event Log for a device that had files encrypted by Quantum ransomware, showing the reads and writes of files with ‘.quantum’ appended to encrypted files, and an HTML ransom note left where the files were encrypted.

 

Figure 8- An example of the ransom note left by the Quantum gang, this one is taken from open-sources [22].


The example in Figure 8 mentions that the attacker also possessed large volumes of victim data.  It is likely that the gigabytes of data exfiltrated over FTP were leveraged as blackmail to further extort the victim organization for payment.  

Darktrace Coverage

 

Figure 9- Timeline of Quantum ransomware incident


If Darktrace/Email was deployed in the prospect’s environment, the initial payload (if delivered through a phishing email) could have been detected and held from the recipient’s inbox. Although DETECT identified anomalous network behaviour at each stage of the attack, since the incident occurred during a trial phase where Darktrace could only detect but not respond, the attack was able to progress through the kill chain. If RESPOND/Network had been configured in the targeted environment, the unusual connections observed during the initial access, C2, reconnaissance and lateral movement stages of the attack could have been blocked. This would have prevented the attackers from delivering the later stage payloads and eventual ransomware into the target network.

It is often thought that a properly implemented backup strategy is sufficient defense against ransomware [23], however as discussed in a previous Darktrace blog, the increasing frequency of double extortion attacks in a world where ‘data is the new oil’ demonstrates that backups alone are not a mitigation for the risk of a ransomware attack [24]. Equally, the lack of preventive defenses in the target’s environment enabled the attacker’s riskier decision to dwell in the network for longer and allowed them to optimize their potential reward. 

Recent crackdowns from law enforcement on ransomware groups have shifted these groups’ approaches to aim for a balance between low risk and significant financial rewards [25]. However, given the Quantum gang only have a 5% market share in Q2 2022, compared to the 13.2% held by LockBit and 16.9% held by BlackCat [26], a riskier strategy may be favourable, as a longer dwell time and double extortion outcome offers a ‘belt and braces’ approach to maximizing the rewards from carrying out this attack. Alternatively, the gaps in-between the attack stages may imply that more than one player was involved in this attack, although this group has not been reported to operate a franchise model before [27]. Whether assisted by others or driving for a risk approach, it is clear that Quantum (like other actors) are continuing to adapt to ensure their financial success. They will continue to be successful until organizations dedicate themselves to ensuring that the proper data protection and network security measures are in place. 

Conclusion 

Ransomware has evolved over time and groups have merged and rebranded. However, this incident of Quantum ransomware demonstrates that regardless of the capability to execute a full attack within hours, prolonging an attack to optimize potential reward by leveraging double extortion tactics is sometimes still the preferred action. The pattern of network activity mirrors the techniques used in other Quantum attacks, however this incident lacked the continuous progression of the group’s attacks reported recently and may represent a change of motives during the process. Knowing that attacker motives can change reinforces the need for organizations to invest in preventative controls- an organization may already be too far down the line if it is executing its backup contingency plans. Darktrace DETECT/Network had visibility over both the early network-based indicators of compromise and the escalation to the later stages of this attack. Had Darktrace also been allowed to respond, this case of Quantum ransomware would also have had a very short dwell time, but a far better outcome for the victim.

Thanks to Steve Robinson for his contributions to this blog.

Appendices

References

[1] https://community.ibm.com/community/user/security/blogs/tristan-reed/2022/07/13/ibm-security-reaqta-vs-quantum-locker-ransomware

 

[2] https://www.bleepingcomputer.com/news/security/quantum-ransomware-seen-deployed-in-rapid-network-attacks/

 

[3], [12], [14], [16], [20] https://thedfirreport.com/2022/04/25/quantum-ransomware/

 

[4] https://www.mandiant.com/sites/default/files/2022-04/M-Trends%202022%20Executive%20Summary.pdf

 

[5] https://cyware.com/news/over-650-healthcare-organizations-affected-by-the-quantum-ransomware-attack-d0e776bb/

 

[6] https://www.kroll.com/en/insights/publications/cyber/bumblebee-loader-linked-conti-used-in-quantum-locker-attacks

 

[7] https://github.com/pan-unit42/tweets/blob/master/2022-06-28-IOCs-for-TA578-IcedID-Cobalt-Strike-and-DarkVNC.txt 

 

[8] https://github.com/stamparm/maltrail/blob/master/trails/static/malware/icedid.txt

 

[9], [15] https://www.cynet.com/blog/shelob-moonlight-spinning-a-larger-web-from-icedid-to-conti-a-trojan-and-ransomware-collaboration/

 

[10] https://www.microsoft.com/security/blog/2021/04/09/investigating-a-unique-form-of-email-delivery-for-icedid-malware/

 

[11] https://twitter.com/0xToxin/status/1564289244084011014

 

[13], [27] https://cybernews.com/security/quantum-ransomware-gang-fast-and-furious/

 

[17] https://www.virustotal.com/gui/domain/gedabuyisi.com/relations

 

[18] https://www.virustotal.com/gui/domain/sezijiru.com/relations.

 

[19] https://github.com/ByteSecLabs/ja3-ja3s-combo/blob/master/master-list.txt 

 

[21] https://www.darkreading.com/perimeter/ftp-hacking-on-the-rise

 

[22] https://www.pcrisk.com/removal-guides/23352-quantum-ransomware

 

[23] https://www.cohesity.com/resource-assets/tip-sheet/5-ways-ransomware-renders-backup-useless-tip-sheet-en.pdf

 

[24] https://www.forbes.com/sites/nishatalagala/2022/03/02/data-as-the-new-oil-is-not-enough-four-principles-for-avoiding-data-fires/ 

 

[25] https://www.bleepingcomputer.com/news/security/access-to-hacked-corporate-networks-still-strong-but-sales-fall/

 

[26] https://www.bleepingcomputer.com/news/security/ransom-payments-fall-as-fewer-victims-choose-to-pay-hackers/ 

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
Nicole Wong
Cyber Security Analyst

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May 6, 2026

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

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Software supply-chain attacks in 2026

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

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

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

1. Why the Axios Compromise Scaled

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

The attack chain was simple yet effective:

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

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

A view from Darktrace

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

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

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

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

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

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

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

2. Why Trivy bypassed security tooling trust

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

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

This was a coordinated multi‑phase attack:

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

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

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

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

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

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

Quest KACE: Legacy Risk, Real Impact

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

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

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

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

The strategic pattern: Ecosystem‑scale adversaries

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

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

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

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

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

Edited by Ryan Traill (Content Manager)

Appendices

References:

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

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

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

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

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

IoCs

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

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

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

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

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

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

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

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

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

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

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

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

- e1ec76a0e1f48901566d53828c34b5dc – MD5 - Possible Quest KACE exploitation payload

- d3beab2e2252a13d5689e9911c2b2b2fc3a41086 – SHA1 - Possible Quest KACE exploitation payload

- ab6677fcbbb1ff4a22cc3e7355e1c36768ba30bbf5cce36f4ec7ae99f850e6c5 – SHA256 - Possible Quest KACE exploitation payload

- 83b7a106a5e810a1781e62b278909396 – MD5 - Possible Quest KACE exploitation payload

- deb4b5841eea43cb8c5777ee33ee09bf294a670d – SHA1 - Possible Quest KACE exploitation payload

- b1b2f1e36dcaa36bc587fda1ddc3cbb8e04c3df5f1e3f1341c9d2ec0b0b0ffaf – SHA256 - Possible Quest KACE exploitation payload

Darktrace Model Detections

Anomalous Connection / Application Protocol on Uncommon Port

Anomalous Server Activity / Outgoing from Server

Anomalous Connection / New User Agent to IP Without Hostname

Anomalous File / EXE from Rare External Location

Anomalous File / Script from Rare External Location

Anomalous Server Activity / New User Agent from Internet Facing System

Anomalous Server Activity / Rare External from Server

Antigena / Network / External Threat / Antigena Suspicious File Block

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

Device / New User Agent

Device / Internet Facing Device with High Priority Alert

Anomalous File / New User Agent Followed By Numeric File Download

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

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May 6, 2026

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

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What are email-delivered prompt injection attacks?

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

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

Recent examples of prompt injection attacks

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

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

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

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

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

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

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

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

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

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

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

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

How does Darktrace catch these types of attacks?

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

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

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

Ask your email provider about email-delivered AI prompt injection

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

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

Questions to ask your email security provider

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

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

Learn more about securing AI in your enterprise.

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