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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.
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
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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].

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.

Overview of the malicious email in the Darktrace / EMAIL console, highlighting Dropbox associated content/link payloads.
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.

Geographical location of the SaaS user
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.

External sites summary for the SaaS account in relation to the source IP 13.74.161[.]104, observed with Registering Security Information.
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.

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.
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)

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

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

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April 30, 2026

Mythos vs Ethos: Defending in an Era of AI‑Accelerated Vulnerability Discovery

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Anthropic’s Mythos and what it means for security teams

Recent attention on systems such as Anthropic Mythos highlights a notable problem for defenders. Namely that disclosure’s role in coordinating defensive action is eroding.

As AI systems gain stronger reasoning and coding capability, their usefulness in analyzing complex software environments and identifying weaknesses naturally increases. What has changed is not attacker motivation, but the conditions under which defenders learn about and organize around risk. Vulnerability discovery and exploitation increasingly unfold in ways that turn disclosure into a retrospective signal rather than a reliable starting point for defense.

Faster discovery was inevitable and is already visible

The acceleration of vulnerability discovery was already observable across the ecosystem. Publicly disclosed vulnerabilities (CVEs) have grown at double-digit rates for the past two years, including a 32% increase in 2024 according to NIST, driven in part by AI even prior to Anthropic’s Mythos model. Most notably XBOW topped the HackerOne US bug bounty leaderboard, marking the first time an autonomous penetration tester had done so.  

The technical frontier for AI capabilities has been described elsewhere as jagged, and the implication is that Mythos is exceptional but not unique in this capability. While Mythos appears to make significant progress in complex vulnerability analysis, many other models are already able to find and exploit weaknesses to varying degrees.  

What matters here is not which model performs best, but the fact that vulnerability discovery is no longer a scarce or tightly bounded capability.

The consequence of this shift is not simply earlier discovery. It is a change in the defender-attacker race condition. Disclosure once acted as a rough synchronization point. While attackers sometimes had earlier knowledge, disclosure generally marked the moment when risk became visible and defensive action could be broadly coordinated. Increasingly, that coordination will no longer exist. Exploitation may be underway well before a CVE is published, if it is published at all.

Why patch velocity alone is not the answer

The instinctive response to this shift is to focus on patching faster, but treating patch velocity as the primary solution misunderstands the problem. Most organizations are already constrained in how quickly they can remediate vulnerabilities. Asset sprawl, operational risk, testing requirements, uptime commitments, and unclear ownership all limit response speed, even when vulnerabilities are well understood.

If discovery and exploitation now routinely precede disclosure, then patching cannot be the first line of defense. It becomes one necessary control applied within a timeline that has already shifted. This does not imply that organizations should patch less. It means that patching cannot serve as the organizing principle for defense.

Defense needs a more stable anchor

If disclosure no longer defines when defense begins, then defense needs a reference point that does not depend on knowing the vulnerability in advance.  

Every digital environment has a behavioral character. Systems authenticate, communicate, execute processes, and access resources in relatively consistent ways over time. These patterns are not static rules or signatures. They are learned behaviors that reflect how an organization operates.

When exploitation occurs, even via previously unknown vulnerabilities, those behavioral patterns change.

Attackers may use novel techniques, but they still need to gain access, create processes, move laterally, and will ultimately interact with systems in ways that diverge from what is expected. That deviation is observable regardless of whether the underlying weakness has been formally named.

In an environment where disclosure can no longer be relied on for timing or coordination, behavioral understanding is no longer an optional enhancement; it becomes the only consistently available defensive signal.

Detecting risk before disclosure

Darktrace’s threat research has consistently shown that malicious activity often becomes visible before public disclosure.

In multiple cases, including exploitation of Ivanti, SAP NetWeaver, and Trimble Cityworks, Darktrace detected anomalous behavior days or weeks ahead of CVE publication. These detections did not rely on signatures, threat intelligence feeds, or awareness of the vulnerability itself. They emerged because systems began behaving in ways that did not align with their established patterns.

This reflects a defensive approach grounded in ‘Ethos’, in contrast to the unbounded exploration represented by ‘Mythos’. Here, Mythos describes continuous vulnerability discovery at speed and scale. Ethos reflects an understanding of what is normal and expected within a specific environment, grounded in observed behavior.

Revisiting assume breach

These conditions reinforce a principle long embedded in Zero Trust thinking: assume breach.

If exploitation can occur before disclosure, patching vulnerabilities can no longer act as the organizing principle for defense. Instead, effective defense must focus on monitoring for misuse and constraining attacker activity once access is achieved. Behavioral monitoring allows organizations to identify early‑stage compromise and respond while uncertainty remains, rather than waiting for formal verification.

AI plays a critical role here, not by predicting every exploit, but by continuously learning what normal looks like within a specific environment and identifying meaningful deviation at machine speed. Identifying that deviation enables defenders to respond by constraining activity back towards normal patterns of behavior.

Not an arms race, but an asymmetry

AI is often framed as fueling an arms race between attackers and defenders. In practice, the more important dynamic is asymmetry.

Attackers operate broadly, scanning many environments for opportunities. Defenders operate deeply within their own systems, and it’s this business context which is so significant. Behavioral understanding gives defenders a durable advantage. Attackers may automate discovery, but they cannot easily reproduce what belonging looks like inside a particular organization.

A changed defensive model

AI‑accelerated vulnerability discovery does not mean defenders have lost. It does mean that disclosure‑driven, patch‑centric models no longer provide a sufficient foundation for resilience.

As vulnerability volumes grow and exploitation timelines compress, effective defense increasingly depends on continuous behavioral understanding, detection that does not rely on prior disclosure, and rapid containment to limit impact. In this model, CVEs confirm risk rather than define when defense begins.

The industry has already seen this approach work in practice. As AI continues to reshape both offense and defense, behavioral detection will move from being complementary to being essential.

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April 27, 2026

How a Compromised eScan Update Enabled Multi‑Stage Malware and Blockchain C2

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The rise of supply chain attacks

In recent years, the abuse of trusted software has become increasingly common, with supply chain compromises emerging as one of the fastest growing vectors for cyber intrusions. As highlighted in Darktrace’s Annual Threat Report 2026, attackers and state-actors continue to find significant value in gaining access to networks through compromised trusted links, third-party tools, or legitimate software. In January 2026, a supply chain compromise affecting MicroWorld Technologies’ eScan antivirus product was reported, with malicious updates distributed to customers through the legitimate update infrastructure. This, in turn, resulted in a multi‑stage loader malware being deployed on compromised devices [1][2].

An overview of eScan exploitation

According to eScan’s official threat advisory, unauthorized access to a regional update server resulted in an “incorrect file placed in the update distribution path” [3]. Customers associated with the affected update servers who downloaded the update during a two-hour window on January 20 were impacted, with affected Windows devices subsequently have experiencing various errors related to update functions and notifications [3].

While eScan did not specify which regional update servers were affected by the malicious update, all impacted Darktrace customer environments were located in the Europe, Middle East, and Africa (EMEA) region.

External research reported that a malicious 32-bit executable file , “Reload.exe”, was first installed on affected devices, which then dropped the 64-bit downloader, “CONSCTLX.exe”. This downloader establishes persistence by creating scheduled tasks such as “CorelDefrag”, which are responsible for executing PowerShell scripts. Subsequently, it evades detection by tampering with the Windows HOSTS file and eScan registry to prevent future remote updates intended for remediation. Additional payloads are then downloaded from its command-and-control (C2) server [1].

Darktrace’s coverage of eScan exploitation

Initial Access and Blockchain as multi-distributed C2 Infrastructure

On January 20, the same day as the aforementioned two‑hour exploit window, Darktrace observed multiple devices across affected networks downloading .dlz package files from eScan update servers, followed by connections to an anomalous endpoint, vhs.delrosal[.]net, which belongs to the attackers’ C2 infrastructure.

The endpoint contained a self‑signed SSL certificate with the string “O=Internet Widgits Pty Ltd, ST=SomeState, C=AU”, a default placeholder commonly used in SSL/TLS certificates for testing and development environments, as well as in malicious C2 infrastructure [4].

Utilizing a multi‑distributed C2 infrastructure, the attackers also leveraged domains linked with the Solana open‑source blockchain for C2 purposes, namely “.sol”. These domains were human‑readable names that act as aliases for cryptocurrency wallet addresses. As browsers do not natively resolve .sol domains, the Solana Naming System (formerly known as Bonfida, an independent contributor within the Solana ecosystem) provides a proxy service, through endpoints such as sol-domain[.]org, to enable browser access.

Darktrace observed devices connecting to blackice.sol-domain[.]org, indicating that attackers were likely using this proxy to reach a .sol domain for C2 activity. Given this behavior, it is likely that the attackers leveraged .sol domains as a dead drop resolver, a C2 technique in which threat actors host information on a public and legitimate service, such as a blockchain. Additional proxy resolver endpoints, such as sns-resolver.bonfida.workers[.]dev, were also observed.

Solana transactions are transparent, allowing all activity to be viewed publicly. When Darktrace analysts examined the transactions associated with blackice[.]sol, they observed that the earliest records dated November 7, 2025, which coincides with the creation date of the known C2 endpoint vhs[.]delrosal[.]net as shown in WHOIS Lookup information [4][5].

WHOIS Look records of the C2 endpoint vhs[.]delrosal[.]net.
Figure 1: WHOIS Look records of the C2 endpoint vhs[.]delrosal[.]net.
 Earliest observed transaction record for blackice[.]sol on public ledgers.
Figure 2: Earliest observed transaction record for blackice[.]sol on public ledgers.

Subsequent instructions found within the transactions contained strings such as “CNAME= vhs[.]delrosal[.]net”, indicating attempts to direct the device toward the malicious endpoint. A more recent transaction recorded on January 28 included strings such as “hxxps://96.9.125[.]243/i;code=302”, suggesting an effort to change C2 endpoints. Darktrace observed multiple alerts triggered for these endpoints across affected devices.

Similar blockchain‑related endpoints, such as “tumama.hns[.]to”, were also observed in C2 activities. The hns[.]to service allows web browsers to access websites registered on Handshake, a decentralized blockchain‑based framework designed to replace centralized authorities and domain registries for top‑level domains. This shift toward decentralized, blockchain‑based infrastructure likely reflects increased efforts by attackers to evade detection.

In outgoing connections to these malicious endpoints across affected networks, Darktrace / NETWORK recognized that the activity was 100% rare and anomalous for both the devices and the wider networks, likely indicative of malicious beaconing, regardless of the underlying trusted infrastructure. In addition to generating multiple model alerts to capture this malicious activity across affected networks, Darktrace’s Cyber AI Analyst was able to compile these separate events into broader incidents that summarized the entire attack chain, allowing customers’ security teams to investigate and remediate more efficiently. Moreover, in customer environments where Darktrace’s Autonomous Response capability was enabled, Darktrace took swift action to contain the attack by blocking beaconing connections to the malicious endpoints, even when those endpoints were associated with seemingly trustworthy services.

Conclusion

Attacks targeting trusted relationships continue to be a popular strategy among threat actors. Activities linked to trusted or widely deployed software are often unintentionally whitelisted by existing security solutions and gateways. Darktrace observed multiple devices becoming impacted within a very short period, likely because tools such as antivirus software are typically mass‑deployed across numerous endpoints. As a result, a single compromised delivery mechanism can greatly expand the attack surface.

Attackers are also becoming increasingly creative in developing resilient C2 infrastructure and exploiting legitimate services to evade detection. Defenders are therefore encouraged to closely monitor anomalous connections and file downloads. Darktrace’s ability to detect unusual activity amidst ever‑changing tactics and indicators of compromise (IoCs) helps organizations maintain a proactive and resilient defense posture against emerging threats.

Credit to Joanna Ng (Associate Principal Cybersecurity Analyst) and Min Kim (Associate Principal Cybersecurity Analyst) and Tara Gould (Malware Researcher Lead)

Edited by Ryan Traill (Content Manager)

Appendices

Darktrace Model Detections

  • Anomalous File::Zip or Gzip from Rare External Location
  • Anomalous Connection / Suspicious Self-Signed SSL
  • Anomalous Connection / Rare External SSL Self-Signed
  • Anomalous Connection / Suspicious Expired SSL
  • Anomalous Server Activity / Anomalous External Activity from Critical Network Device

List of Indicators of Compromise (IoCs)

  • vhs[.]delrosal[.]net – C2 server
  • tumama[.]hns[.]to – C2 server
  • blackice.sol-domain[.]org – C2 server
  • 96.9.125[.]243 – C2 Server

MITRE ATT&CK Mapping

  • T1071.001 - Command and Control: Web Protocols
  • T1588.001 - Resource Development
  • T1102.001 - Web Service: Dead Drop Resolver
  • T1195 – Supple Chain Compromise

References

[1] https://www.morphisec.com/blog/critical-escan-threat-bulletin/

[2] https://www.bleepingcomputer.com/news/security/escan-confirms-update-server-breached-to-push-malicious-update/

[3] hxxps://download1.mwti.net/documents/Advisory/eScan_Security_Advisory_2026[.]pdf

[4] https://www.virustotal.com/gui/domain/delrosal.net

[5] hxxps://explorer.solana[.]com/address/2wFAbYHNw4ewBHBJzmDgDhCXYoFjJnpbdmeWjZvevaVv

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About the author
Joanna Ng
Associate Principal Analyst
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