Detecting and Mitigating Adversary-in-the-Middle Phishing Attacks with Darktrace Services
Threat actors often use advanced phishing toolkits and Adversary-in-the-Middle (AitM) attacks in Business Email Compromise (BEC) campaigns, Discover how Darktrace detected and mitigated a sophisticated attack leveraging Dropbox, highlighting the importance of robust cybersecurity measures.
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
Justin Torres
Cyber Analyst
Share
09
Jan 2025
What is an Adversary-in-the-Middle Attack?
Threat actors are increasingly utilizing advanced phishing toolkits and techniques to carry out Adversary-in-the-Middle (AitM) attacks. These attacks involve the use of a proxy to a legitimate service, where the attacker’s webpage mimics the expected site. While the victim believes they are visiting the legitimate site, they are actually interacting with the attacker’s device, allowing the malicious actor to monitor all interactions and control the authenticated session, ultimately gaining access to the user’s account [1][2].
In these types of AitM BEC attacks, recipients are often targeted with Dropbox-related emails, featuring subject headings like ‘FirstLast shared "Filename" with you,’ which suggest an individual is sharing an invoice-related attachment. These email subjects are common in such attacks, as threat actors attempt to encourage victims to access Dropbox links by masquerading them as legitimate files.
While higher priority users are, of course, targeted, the scope of these attacks remains broad. For instance, if a lower priority user is targeted by a phishing attack or their token is stolen, an attacker can still attempt BEC for further malicious intent and financial gain.
In October 2024, a Darktrace customer received a phishing email from a seemingly legitimate Dropbox address. This email originated from the IP, 54.240.39[.]219 and contained multiple link payloads to Dropbox-related hostnames were observed, inviting the user to access a file. Based on anomaly indicators and detection by Darktrace / EMAIL, Darktrace recognized that one of the payloads was attempting to abuse a legitimate cloud platform to share files or other unwanted material with the recipient.
Figure 1: Overview of the malicious email in the Darktrace / EMAIL console, highlighting Dropbox associated content/link payloads.
Following the recipient’s engagement with this email, Darktrace / IDENTITY identified a series of suspicious activities within the customer’s environment.
AitM attacks allow threat actors to bypass multi-factor authentication (MFA). Initially, when a user is phished, the malicious infrastructure captures both the user’s credentials and the token. This includes replaying a token issued to user that has already completed the MFA requirement, allowing the threat actor to satisfy the validity of the requirement and gain access to sensitive organizational resources. Darktrace is able to analyze user activity and authentication patterns to determine whether MFA requirements were met. This capability helps verify and indicate token theft via AitM.
Darktrace observed the associated user account making requests over Microsoft 365 from the IP 41.90.175[.]46. Given the unusual nature and rare geolocation based in Kenya, Africa, this activity did not appear indicative of legitimate business operations.
Figure 2: Geographical location of the SaaS user in relation to the source IP 41.90.175[.]46.
Further analysis using open-source intelligence (OSINT) revealed that the endpoint was likely associated with a call-back proxy network [3]. This suggested the presence of a network device capable of re-routing traffic and harvesting information.
Darktrace also detected that the same SaaS user was logging in from two different locations around the same time. One login was from a common, expected location, while the other was from an unusual location. Additionally, the user was observed registering security information using the Microsoft Authenticator app, indicating an attempt by an attacker to maintain access to the account by establishing a new method of MFA. This new MFA method could be used to bypass future MFA requirements, allowing the attacker to access sensitive material or carry out further malicious activities.
Figure 3: External sites summary for the SaaS account in relation to the source IP 13.74.161[.]104, observed with Registering Security Information.
Ultimately, this anomalous behavior was escalated to the Darktrace Security Operations Centre (SOC) via the Managed Detection & Response service for prompt triage and investigation by Darktrace’s SOC Analysts who notified the customer of strong evidence of compromise.
Fortunately, since this customer had Darktrace enabled in Autonomous Response mode, the compromised SaaS account had already been disabled, containing the attack. Darktrace’s SOC elected to extend this action to ensure the malicious activity remained halted until the customer could take further remedial action.
Figure 4: Attack timeline of observed activity, in chronological order; This highlighted anomalous SaaS events such as, MailItemsAccessed’, ‘Use of Unusual Credentials’, ‘User Registered Security Info’ events, and a ‘Disable User’ Autonomous Response action.
Conclusion
AitM attacks can play a crucial role in BEC campaigns. These attacks are often part of multi-staged operations, where an initial AitM attack is leveraged to launch a BEC by delivering a malicious URL through a trusted vendor or service. Attackers often attempt to lay low on their target network, sometimes persisting for extended periods, as they monitor user accounts or network segments to intercept sensitive communications.
In this instance, Darktrace successfully identified and acted against AitM techniques being leveraged in a BEC attack that used Dropbox for delivery. While Dropbox is widely used for legitimate purposes, its popularity has also made it a target for exploitation by threat actors, who have used it for a variety of malicious purposes, including delivering malware and revealing sensitive information.
Darktrace’s Security Operations Support service, combined with its Autonomous Response technology, provided timely and effective mitigation. Dedicated Security Operations Support analysts triaged the incident and implemented preventative measures, ensuring the customer was promptly notified. Meanwhile, Darktrace swiftly disabled the compromised SaaS account, allowing the customer to take further necessary actions, such as resetting the user’s password.
This case highlights the capabilities of Darktrace’s solutions, enabling the customer to resume normal business operations despite the malicious activity.
Credit to Justin Torres (Senior Cyber Analyst), Stefan Rowe (Technical Director, SOC) and Ryan Traill (Analyst Content Lead)
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.
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)
![External sites summary for the SaaS account in relation to the source IP 13.74.161[.]104, observed with Registering Security Information.](https://cdn.prod.website-files.com/626ff4d25aca2edf4325ff97/6780ea0192cfaa7b91ae27e0_6780e802ab646602ed571ce1_Pasted%2520Graphic%25202.avif)
![Variation in URLs over time within the same hola[.]org domain, indicating the use of dynamically changing endpoints.](https://cdn.prod.website-files.com/626ff4d25aca2edf4325ff97/6a304bdeff111215c0436931_Screenshot%202026-06-15%20at%2012.00.43%E2%80%AFPM.avif)
![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.avif)
