Learn how Darktrace leveraged generative AI tools to detect and combat phishing email campaigns. Discover how AI is reshaping cybersecurity strategies.
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
Germaine Tan
VP, Security & AI Strategy, Field CISO
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26
Sep 2023
Stopping the bad while allowing the good
Since its inception, email has been regarded as one of the most important tools for businesses, revolutionizing communication and allowing global teams to become even more connected. But besides organizations heavily relying on email for their daily operations, threat actors have also recognized that the inbox is one of the easiest ways to establish an initial foothold on the network.
Today, not only are phishing campaigns and social engineering attacks becoming more prevalent, but the level of sophistication of these attacks are also increasing with the help of generative AI tools that allow for the creation of hyper-realistic emails with minimal errors, effectively lowering the barrier to entry for threat actors. These diverse and stealthy types of attacks evade traditional email security tools based on rules and signatures, because they are less likely to contain the low-sophistication markers of a typical phishing attack.
In a situation where the sky is the limit for attackers and security teams are lean, how can teams equip themselves to tackle these threats? How can they accurately detect increasingly realistic malicious emails and neutralize these threats before it is too late? And importantly, how can email security block these threats while allowing legitimate emails to flow freely?
Instead of relying on past attack data, Darktrace’s Self-Learning AI detects the slightest deviation from a user’s pattern of life and responds autonomously to contain potential threats, stopping novel attacks in their tracks before damage is caused. It doesn’t define ‘good’ and ‘bad’ like traditional email tools, rather it understands each user and what is normal for them – and what’s not.
This blog outlines how Darktrace / EMAIL™ used its understanding of ‘normal’ to accurately detect and respond to a sustained phishing campaign targeting a real-life company.
Responding to a sustained phishing attack
Over the course of 24 hours, Darktrace detected multiple emails containing different subjects, all from different senders to different recipients in one organization. These emails were sent from different IP addresses, but all came from the same autonomous system number (ASN).
Figure 1: The sender freemail addresses and subject lines all followed a certain format. The subject lines followed the format of “<First name> <Last name>”, possibly to induce curiosity. The senders were all freemail accounts and contained first names, last names and some numbers, showing the attempts to make these email addresses appear legitimate.
The emails themselves had many suspicious indicators. All senders had no prior association with the recipient, and the emails generated a high general inducement score. This score is generated by structural and non-specific content analysis of the email – a high score indicates that the email is trying to induce the recipient into taking a particular action, which may lead to account compromise.
Additionally, each email contained a visually prominent link to a file storage service, hidden behind a shortened bit.ly link. The similarities across all these emails pointed to a sustained campaign targeting the organization by a single threat actor.
Figure 2: One of the emails is shown above. Like all the other emails, it contained a highly suspicious and shortened link.
Figure 3: In another one of the emails, the link observed had similar characteristics. But this email stands out from the rest. The sender's name seems to be randomly set – the 3 alphabets are close to each other on the keyboard.
With all these suspicious indicators, many models were breached. This drove up the anomaly score, causing Darktrace/Email to hold all suspicious emails from the recipients’ inboxes, safeguarding the recipients from potential account compromise and disallowing the threats from taking hold in the network.
Imagining a phishing attack without Darktrace/Email
So what could have happened if Darktrace had not withheld these emails, and the recipients had clicked on the links? File storage sites have a wide variety of uses that allow attackers to be creative in their attack strategy. If the user had clicked on the shortened link, the possible consequences are numerous. The link could have led to a login page for unsuspecting victims to input their credentials, or it could have hosted malware that would automatically download if the link was clicked. With the compromised credentials, threat actors could even bypass MFA, change email rules, or gain privileged access to a network. The downloaded malware might also be a keylogger, leading to cryptojacking, or could open a back door for threat actors to return to at a later time.
Figure 4: Darktrace / EMAIL highlights suspicious link characteristics and provides an option to preview the pages.
Figure 5: At the point of writing, both links could not be reached. This could be because they were one-time unique links created specifically for the user, and can no longer be accessed once the campaign has ceased.
The limits of traditional email security tools
Secure email gateways (SEGs) and static AI security tools may have found it challenging to detect this phishing campaign as malicious. While Darktrace was able to correlate these emails to determine that a sustained phishing campaign was taking place, the pattern among these emails is far too generic for specific rules as set in traditional security tools. If we take the characteristic of the freemail account sender as an example, setting a rule to block all emails from freemail accounts may lead to more legitimate emails being withheld, since these addresses have a variety of uses.
With these factors in mind, these emails could have easily slipped through traditional security filters and led to a devastating impact on the organization.
Conclusion
As threat actors step up their attacks in sophistication, prioritizing email security is more crucial than ever to preserving a safe digital environment. In response to these challenges, Darktrace / EMAIL offers a set-and-forget solution that continuously learns and adapts to changes in the organization.
Through an evolving understanding of every environment in which it is deployed, its threat response becomes increasingly precise in neutralizing only the bad, while allowing the good – delivering email security that doesn’t come at the expense of business growth.
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.
Journey of a Threat: How Multi-Layered AI Works in Darktrace / EMAIL
Follow a malicious email as it moves through Darktrace / EMAIL’s multi-layered AI system, from raw data to final decision. Each layer works together to detect threats, understand intent, and take autonomous action.
How email-delivered prompt injection attacks can target enterprise AI – and why it matters
Prompt injection is a newly emerging threat, with only a handful of confirmed victims so far – targeting how AI systems use data rather than exploiting traditional software vulnerabilities. As agentic AI becomes embedded across enterprise environments, attackers may attempt to manipulate these systems through hidden instructions in everyday email content.
Darktrace Unites Human Behavior and Threat Detection Across Email, Slack, Teams, and Zoom
Introducing the adaptive era of email security: a unified platform that connects personalized coaching, collaboration tools, and user behavior into a self-improving defense system.
Hola VPN Abuse: From Proxy Traffic to Malware and Cryptomining
Introduction
In enterprise environments, non-compliant software traffic can introduce unexpected exposure by creating unmanaged paths for outbound connectivity. Hola VPN is a notable example because of its peer-to-peer design, which can effectively turn user devices into routing or exit nodes for other parties’ traffic, shifting the risk profile from that of a traditional virtual private network (VPN) to something closer to a distributed proxy.
As a result, the appearance of Hola-related activity, whether from prior installation or unintended background connections, should be treated with caution. Such activity may provide a foothold for malicious behavior, including lateral movement or command-and-control communication.
This blog explores how Hola-associated activity appeared as part of broader patterns of suspicious behavior observed across the Darktrace customer base.
The campaign
In February and March 2026, Darktrace observed similar anomalous activity across multiple customer environments, with affected devices showing consistent behavioral patterns. These included connections to multiple *.hola[.]org endpoints using Hola-related user agents, suggesting interaction with Hola infrastructure rather than isolated or incidental traffic.
Following these connections, affected customer environments showed downloads of suspicious executable files from rare external endpoints 188.241.219[.]55 and 184.241.218[.]111. Both endpoints have been flagged as potentially malicious by open-source intelligence (OSINT) [1][2].
These downloads were conducted using consistent user agents across impacted customers, specifically ‘Hola svc_js_win32/1.249.408’ and ‘Hola svc_js_win32/1.251.389’, suggesting a possible association with Hola-related activity.
Notably, this pattern aligns with recent reporting that, in some cases, Hola distributed an undeclared executable component, me[.]exe, which was later assessed to be a likely Monero-mining binary introduced via a compromised delivery pipeline [3].
Case Study 1
Darktrace first observed a new device on January 19, 2026, within a customer environment based in the Europe, Middle East, and Africa (EMEA) region. On the same day it appeared on the network, the device communicated with multiple pieces of Hola VPN-linked infrastructure before downloading a binary from a hola[.]org subdomain.
Figure 1: Cyber AI Analyst investigation highlighting Hola VPN service activity potentially associated with subsequent HTTP command-and-control (C2) connections.
Subsequent Darktrace telemetry revealed a recurring pattern of activity from the day the device was first observed through to March 4, 2026. During this period, the device repeatedly issued HTTP GET requests to the URI /bwfile?size=1048576, each returning a 200 OK response, indicating successful file retrieval.
This behavior was accompanied by a POST request to /bwfile, followed by an additional GET request for a significantly larger file at /bwfile?size=26214400, suggesting a deliberate and structured file transfer pattern.
Notably, the binary download activity was not tied to a single static host. Instead, it was observed across multiple URLs that changed over time while remaining within the same hola[.]org domain. This pattern suggests the use of rotating or distributed delivery infrastructure rather than a fixed endpoint.
Figure 2: Variation in URLs over time within the same hola[.]org domain, indicating the use of dynamically changing endpoints.
Across these events, the activity was consistently associated with the user agent Hola svc_js_win32/1.249.408, further linking the traffic to Hola-related service components. Amid these persistent and unusual connections, on February 22, Darktrace observed the device connecting to 188.241.219[.]55/proxy-peer-windows-amd64[.]exe, resulting in the download of an executable file.
Figure 3: File transfer event showing the download of an executable from the rare external endpoint 188.241.219[.]55.
Based on its file hash, the downloaded file was assessed as a likely Trojan downloader [4], with import hash (imphash) values showing similarities to samples linked to Vidar, Rhadamanthys, and Stealc according to OSINT [5]. Overall, this sequence of activity suggests that Hola-related connectivity may have been leveraged as part of a broader malware delivery chain.
Darktrace’s Autonomous Response
Due to the highly unusual activity observed, Darktrace Autonomous Response was triggered by the device’s behavior. However, as the customer deployment was configured in “Human Confirmation” mode, manual approval was required before any action could be taken.
Had the deployment been set to “Fully Autonomous” mode, Darktrace would have automatically:
Blocked connections to the associated ports and external endpoints
Prevented all outgoing network connections from the device
Enforced the device’s established ‘pattern of life’, allowing normal activity to continue while restricting any anomalous behavior
Figure 4: Example of a Darktrace Autonomous Response model highlighting the action that would have been taken, demonstrating how the system identifies anomalous behavior and applies targeted containment measures to restrict suspicious network activity.
Case Study 2
While the first case focused on anomalous activity from a newly observed device, Darktrace also identified cases in which devices had already been communicating with Hola-related endpoints prior to the suspected campaign. This may suggest pre-existing Hola usage within the environment, potentially increasing exposure and creating an avenue for subsequent suspicious activity.
One case involved three devices within a customer network based in the Americas (AMS). In this instance, a different payload was identified: me[.]exe, a potentially malicious cryptocurrency miner also referred to as HolaMonitorService[.]exe [6][7]. The downloads were observed from infrastructure similar to that seen in Case 1, including an IP address within the same 188.241.0.0/16 subnet.
Connections to *.hola[.]org, alongside the use of potential Hola-related user agents consistent with those in Case 1, were also identified, further suggesting a link between the observed activity and Hola-associated infrastructure.
Darktrace observed activity indicative of unusual VPN usage on the first affected device on February 2, followed by telemetry suggesting potential Tor usage. This was later followed by the download of me[.]exe on March 10 from 188.241.218[.]111. Notably, this device was the earliest among the three within the deployment to exhibit the presence of the suspicious executable.
Figure 5: Cyber AI Analyst detection highlighting the download of a suspicious executable from a similar external endpoint in a separate deployment.
On March 5, 2026, the second affected device exhibited a slightly different progression, initiating connections to http-test1[.]hola[.]org using the user agent ‘hola_get’. This activity was followed by the download of me[.]exe from the same endpoint on March 13, consistent with the broader pattern of Hola-related downloads observed across the environment.
Figure 6: Example of Hola VPN-related connectivity observed on the network prior to the suspected campaign, indicating pre-existing usage that may have contributed to subsequent activity.
The final affected device within this customer’s network demonstrated a more limited but related pattern, also downloading me[.]exe on March 17 using the same ‘hola_get’ user agent.
While the earlier Hola VPN usage observed across the deployment may not have been directly related to the suspected malware campaign, it may nonetheless have contributed to reduced visibility. The presence of pre-existing Hola-related traffic could have obscured malicious activity, making it more difficult to distinguish legitimate usage from attacker-driven behavior and, in turn, hindering the timely identification of the emerging compromise.
Darktrace’s Autonomous Response
For this deployment, the customer had their Autonomous Response capability configured in “Fully Autonomous” mode, allowing Darktrace to take action without human intervention. As a result, the system was able to autonomously disrupt the activity as soon as relevant events were identified through model detections.
Figure 7: Darktrace Autonomous Response actions taken against suspicious activity linked to Hola VPN.
Suspected cryptomining activity
As previously noted, some of the observed executable payloads appear to be linked to cryptomining malware. Across a subset of affected customer environments, this assessment was further supported by subsequent device activity consistent with Monero mining. Affected devices established follow-on connections to multiple external endpoints aligned with known mining infrastructure, indicating post-download execution.
Considering the broader sequence of activity, this pattern may point to a wider form of abuse in which legitimate VPN-related traffic is used to mask or facilitate malicious behavior following compromise.
On several devices, the download of executable files, including a newly observed peer[.]exe, was followed by alerts indicative of cryptocurrency mining activity. Mining-related credentials such as ‘x’ were observed using the Minergate protocol to communicate with endpoints within the 89.125.255.0/24 subnet and 188.241.218[.]111, the same endpoint involved in earlier download activity. Additional credentials appeared to reflect device-specific CPU identifiers, for example ‘12th Gen Intel(R) Core (TM) i5-1235U’.
Observed mining methods included login, submit, and job, consistent with active participation in a pool-based mining workflow rather than passive or incidental contact. The login method indicates that the host authenticated to the mining service as a worker, job reflects the assignment of computational tasks, and submit shows completed work being returned to the pool [8]. This sequence suggests that affected devices were actively contributing processing resources as part of an unauthorized distributed mining operation.
The presence of unauthorized cryptominers can lead to degraded system performance and reduced device stability. Beyond the immediate resource impact, such activity often serves as an indicator of a broader compromise rather than an isolated issue. This may increase the risk of further malware deployment, persistence mechanisms, and lateral movement, particularly in environments where the initial intrusion has not been fully contained.
Conclusion
Across affected environments, detections such as unusual VPN usage, connections to Hola infrastructure, anomalous HTTP activity, suspicious file downloads, and subsequent cryptomining behavior were linked into a single, evolving incident narrative. This aggregation provided a clearer view of attack progression, enabling security teams to understand not just isolated alerts, but the full sequence of compromise from initial contact through to post-exploitation.
Ultimately, these activities show that the risk posed by non-compliant software such as Hola VPN can extend far beyond simple policy violations. What began as traffic to Hola-related infrastructure was, in multiple cases, followed by behavior suggesting deliberate misuse, including suspicious executable downloads using Hola-related user agents and, in some instances, evidence of active cryptomining. These were not isolated anomalies, but elements of a broader pattern in which seemingly benign proxy or VPN-related communications may have created a pathway for malicious delivery and unauthorized resource exploitation.
The significance of this activity lies not only in the downloads or mining, but in what it reveals about an attacker’s ability to blend malicious operations into traffic associated with software that may already have a foothold in the environment. When unapproved software operates within an enterprise, it can reduce visibility, blur the distinction between legitimate and malicious traffic, and create opportunities to extend compromise in ways that are persistent and difficult to detect. Darktrace’s anomaly-based approach enables these behavioral distinctions to be identified, regardless of whether the device is new or long established within the network.
Credit to Min Kim (Associate Principal Analyst), Priya Thapa (Senior Cyber Analyst) Edited by Ryan Traill (Content Manager)
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![File transfer event showing the download of an executable from the rare external endpoint 188.241.219[.]55.](https://cdn.prod.website-files.com/626ff4d25aca2edf4325ff97/6a304c2468d20aeff16a2721_Screenshot%202026-06-15%20at%2012.01.53%E2%80%AFPM.png)
