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.
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.
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.](https://cdn.prod.website-files.com/626ff4d25aca2edf4325ff97/6780ea0192cfaa7b91ae27e0_6780e802ab646602ed571ce1_Pasted%2520Graphic%25202.avif)
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.
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
![Darktrace’s detection of the unusual external connection to 142.11[.]206[.]73 via port 8000.](https://cdn.prod.website-files.com/626ff4d25aca2edf4325ff97/69fa6d343ee828935a4a00f5_Screenshot%202026-05-05%20at%203.20.33%E2%80%AFPM.png)
