January 9, 2025

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.

Written by

Justin Torres

Cyber Analyst

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

Justin Torres

Cyber Analyst

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].

This blog will explore how Darktrace detected AitM techniques being leveraged in a Business Email Compromise (BEC) attack that used the widely used and trusted cloud storage service, Dropbox, for delivery. Dropbox’s popularity has made it a prime target for attackers to exploit in recent years. Threat actors can exploit the service for various malicious activities, including distributing malware and exposing sensitive information.

Attack Overview

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)

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Appendices

References

1. https://www.proofpoint.com/us/threat-reference/man-in-the-middle-attack-mitm

2. https://thehackernews.com/2024/08/how-to-stop-aitm-phishing-attack.html

3. https://spur.us/context/41.90.175.46

Darktrace Model Detections

Darktrace / NETWORK Model Alert(s):

SaaS / Compromise::SaaS Anomaly Following Anomalous Login

SaaS / Unusual Activity::Multiple Unusual SaaS Activities

SaaS / Compromise::Unusual Login and Account Update

SaaS / Compromise::Login From Rare Endpoint While User Is Active

SaaS / Access::Unusual External Source for SaaS Credential Use

SaaS / Email Nexus::Unusual Login Location Following Link to File Storage

SaaS / Access::MailItemsAccessed from Rare Endpoint

Darktrace/Autonomous Response Model Alert(s):

Antigena / SaaS::Antigena Suspicious SaaS Activity Block

List of Indicators of Compromise (IoCs)

(IoC - Type - Description)

41.90.175[.]46 – Source IP Observed with Suspicious Login Behavior

MITRE ATT&CK Mapping

(Technique Name - Tactic - ID - Sub-Technique of)

Cloud Accounts - DEFENSE EVASION, PERSISTENCE, PRIVILEGE ESCALATION, INITIAL ACCESS - T1078.004 - T1078

Email Accounts - RESOURCE DEVELOPMENT - T1586.002 - T1586

Cloud Service Dashboard - DISCOVERY - T1538

Compromise Accounts - RESOURCE DEVELOPMENT - T1586

Steal Web Session Cookie - CREDENTIAL ACCESS - T1539

Written by

Justin Torres

Cyber Analyst

Inside the SOC

Written by

Justin Torres

Cyber Analyst

Associate Principal Analyst & Regional Consultancy Lead

•

March 26, 2026

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March 26, 2026

Phantom Footprints: Tracking GhostSocks Malware

Why are attackers using residential proxies?

In today's threat landscape, blending in to normal activity is the key to success for attackers and the growing reliance on residential proxies shows a significant shift in how threat actors are attempting to bypass IP detection tools.

The increasing dependency on residential proxies has exposed how prevalent proxy services are and how reliant a diverse range of threat actors are on them. From cybercriminal groups to state‑sponsored actors, the need to bypass IP detection tools is fundamental to the success of these groups. One malware that has quietly become notorious for its ability to avoid anomaly detection is GhostSocks, a malware that turns compromised devices into residential proxies.

What is GhostSocks?

Originally marketed on the Russian underground forum xss[.]is as a Malware‑as‑a‑Service (MaaS), GhostSocks enables threat actors to turn compromised devices into residential proxies, leveraging the victim's internet bandwidth to route malicious traffic through it.

How does Ghostsocks malware work?

The malware offers the threat actor a “clean” IP address, making it look like it is coming from a household user. This enables the bypassing of geographic restrictions and IP detection tools, a perfect tool for avoiding anomaly detection. It wasn’t until 2024, when a partnership was announced with the infamous information stealer Lumma Stealer, that GhostSocks surged into widespread adoption and alluded to who may be the author of the proxy malware.

Written in GoLang, GhostSocks utilizes the SOCKS5 proxy protocol, creating a SOCKS5 connection on infected devices. It uses a relay‑based C2 implementation, where an intermediary server sits in between the real command-and-control (C2) server and the infected device.

How does Ghostsocks malware evade detection?

To further increase evasion, the Ghostsocks malware wraps its SOCKS5 tunnels in TLS encryption, allowing its malicious traffic to blend into normal network traffic.

Early variants of GhostSocks do not implement a persistence mechanism; however, later versions achieve persistence via registry run keys, ensuring sustained proxy operational time [1].

While proxying is its primary purpose, GhostSocks also incorporates backdoor functionality, enabling malicious actors to run arbitrary commands and download and deploy additional malicious payloads. This was evident with the well‑known ransomware group Black Basta, which reportedly used GhostSocks as a way of maintaining long‑term access to victims’ networks [1].

Darktrace’s detection of GhostSocks Malware

Darktrace observed a steady increase in GhostSocks activity across its customer base from late 2025, with its Threat Research team identifying multiple incidents involving the malware. In one notable case from December 2025, Darktrace detected GhostSocks operating alongside Lumma Stealer, reinforcing that the partnership between Lumma and GhostSocks remains active despite recent attempts to disrupt Lumma’s infrastructure.

Darktrace’s first detection of GhostSocks‑related activity came when a device on the network of a customer in the education sector began making connections to an endpoint with a suspicious self‑signed certificate that had never been seen on the network before.

The endpoint in question, 159.89.46[.]92 with the hostname retreaw[.]click, has been flagged by multiple open‑source intelligence (OSINT) sources as being associated with Lumma Stealer’s C2 infrastructure [2], indicating its likely role in the delivery of malicious payloads.

Figure 1: Darktrace’s detection of suspicious SSL connections to retreaw[.]click, indicating an attempted link to Lumma C2 infrastructure.

Less than two minutes later, Darktrace observed the same device downloading the executable (.exe) file “Renewable.exe” from the IP 86.54.24[.]29, which Darktrace recognized as 100% rare for this network.

Figure 2: Darktrace’s detection of a device downloading the unusual executable file “Renewable.exe”.

Both the file MD5 hash and the executable itself have been identified by multiple OSINT vendors as being associated with the GhostSocks malware [3], with the executable likely the backdoor component of the GhostSocks malware, facilitating the distribution of additional malicious payloads [4].

Following this detection, Darktrace’s Autonomous Response capability recommended a blocking action for the device in an early attempt to stop the malicious file download. In this instance, Darktrace was configured in Human Confirmation Mode, meaning the customer’s security team was required to manually apply any mitigative response actions. Had Autonomous Response been fully enabled at the time of the attack, the connections to 86.54.24[.]29 would have been blocked, rendering the malware ineffective at reaching its C2 infrastructure and halting any further malicious communication.

Figure 3: Darktrace’s Autonomous Response capability suggesting blocking the suspicious connections to the unusual endpoint from which the malicious executable was downloaded.

As the attack was able to progress, two days later the device was detected downloading additional payloads from the endpoint www.lbfs[.]site (23.106.58[.]48), including “Setup.exe”, “,.exe”, and “/vp6c63yoz.exe”.

Figure 4: Darktrace’s detection of a malicious payload being downloaded from the endpoint www.lbfs[.]site.

Once again, Darktrace recognized the anomalous nature of these downloads and suggested that a “group pattern of life” be enforced on the offending device in an attempt to contain the activity. By enforcing a pattern of life on a device, Darktrace restricts its activity to connections and behaviors similar to those performed by peer devices within the same group, while still allowing it to carry out its expected activity, effectively preventing deviations indicative of compromise while minimizing disruption. As mentioned earlier, these mitigative actions required manual implementation, so the activity was able to continue. Darktrace proceeded to suggest further actions to contain subsequent malicious downloads, including an attempt to block all outbound traffic to stop the attack from progressing.

Figure 5: An overview of download activity and the Autonomous Response actions recommended by Darktrace to block the downloads.

Around the same time, a third executable download was detected, this time from the hostname hxxp[://]d2ihv8ymzp14lr.cloudfront.net/2021-08-19/udppump[.]exe, along with the file “udppump.exe”.While GhostSocks may have been present only to facilitate the delivery of additional payloads, there is no indication that these CloudFront endpoints or files are functionally linked to GhostSocks. Rather, the evidence points to broader malicious file‑download activity.

Shortly after the multiple executable files had been downloaded, Darktrace observed the device initiating a series of repeated successful connections to several rare external endpoints, behavior consistent with early-stage C2 beaconing activity.

Cyber AI Analyst’s investigation

Figure 7: Darktrace’s detection of additional malicious file downloads from malicious CloudFront endpoints.

Throughout the course of this attack, Darktrace’s Cyber AI Analyst carried out its own autonomous investigation, piecing together seemingly separate events into one wider incident encompassing the first suspicious downloads beginning on December 4, the unusual connectivity to many suspicious IPs that followed, and the successful beaconing activity observed two days later. By analyzing these events in real-time and viewing them as part of the bigger picture, Cyber AI Analyst was able to construct an in‑depth breakdown of the attack to aid the customer’s investigation and remediation efforts.

Figure 8: Cyber AI Analyst investigation detailing the sequence of events on the compromised device, highlighting its extensive connectivity to rare endpoints, the related malicious file‑download activity, and finally the emergence of C2 beaconing behavior.

Conclusion

The versatility offered by GhostSocks is far from new, but its ability to convert compromised devices into residential proxy nodes, while enabling long‑term, covert network access—illustrates how threat actors continue to maximise the value of their victims’ infrastructure. Its growing popularity, coupled with its ongoing partnership with Lumma, demonstrates that infrastructure takedowns alone are insufficient; as long as threat actors remain committed to maintaining anonymity and can rapidly rebuild their ecosystems, related malware activity is likely to persist in some form.

Credit to Isabel Evans (Cyber Analyst), Gernice Lee (Associate Principal Analyst & Regional Consultancy Lead – APJ)
Edited by Ryan Traill (Content Manager)