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)

‍

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

•

September 8, 2025

Emma Foulger

Global Threat Research Operations Lead

Network

•

September 9, 2025

Watch the NIS2 Webinar

Blog

Network

September 9, 2025

The benefits of bringing together network and email security

In many organizations, network and email security operate in isolation. Each solution is tasked with defending its respective environment, even though both are facing the same advanced, multi-domain threats.

This siloed approach overlooks a critical reality: email remains the most common vector for initiating cyber-attacks, while the network is the primary stage on which those attacks progress. Without direct integration between these two domains, organizations risk leaving blind spots that adversaries can exploit.

A modern security strategy needs to unify email and network defenses, not just in name, but in how they share intelligence, conduct investigations, and coordinate response actions. Let’s take a look at how this joined-up approach delivers measurable technical, operational, and commercial benefits.

Technical advantages

Pre-alert intelligence: Gathering data before the threat strikes

Most security tools start working when something goes wrong – an unusual login, a flagged attachment, a confirmed compromise. But by then, attackers may already be a step ahead.

By unifying network and email security under a single AI platform (like the Darktrace Active AI Security Platform), you can analyze patterns across both environments in real time, even when there are no alerts. This ongoing monitoring builds a behavioral understanding of every user, device, and domain in your ecosystem.

That means when an email arrives from a suspicious domain, the system already knows whether that domain has appeared on your network before – and whether its behavior has been unusual. Likewise, when new network activity involves a domain first spotted in an email, it’s instantly placed in the right context.

This intelligence isn’t built on signatures or after-the-fact compromise indicators – it’s built on live behavioral baselines, giving your defenses the ability to flag threats before damage is done.

Alert-related intelligence: Connecting the dots in real time

Once an alert does fire, speed and context matter. The Darktrace Cyber AI Analyst can automatically investigate across both environments, piecing together network and email evidence into a single, cohesive incident.

Instead of leaving analysts to sift through fragmented logs, the AI links events like a phishing email to suspicious lateral movement on the recipient’s device, keeping the full attack chain intact. Investigations that might take hours – or even days – can be completed in minutes, with far fewer false positives to wade through.

This is more than a time-saver. It ensures defenders maintain visibility after the first sign of compromise, following the attacker as they pivot into network infrastructure, cloud services, or other targets. That cross-environment continuity is impossible to achieve with disconnected point solutions or siloed workflows.

Operational advantages

Streamlining SecOps across teams

In many organizations, email security is managed by IT, while network defense belongs to the SOC. The result? Critical information is scattered between tools and teams, creating blind spots just when you need clarity.

When email and network data flow into a single platform, everyone is working from the same source of truth. SOC analysts gain immediate visibility into email threats without opening another console or sending a request to another department. The IT team benefits from the SOC’s deeper investigative context.

The outcome is more than convenience: it’s faster, more informed decision-making across the board.

Reducing time-to-meaning and enabling faster response

A unified platform removes the need to manually correlate alerts between tools, reducing time-to-meaning for every incident. Built-in AI correlation instantly ties together related events, guiding analysts toward coordinated responses with higher confidence.

Instead of relying on manual SIEM rules or pre-built SOAR playbooks, the platform connects the dots in real time, and can even trigger autonomous response actions across both environments simultaneously. This ensures attacks are stopped before they can escalate, regardless of where they begin.

Commercial advantages

While purchasing “best-of-breed" for all your different tools might sound appealing, it often leads to a patchwork of solutions with overlapping costs and gaps in coverage. However good a “best-in-breed" email security solution might be in the email realm, it won't be truly effective without visibility across domains and an AI analyst piecing intelligence together. That’s why we think “best-in-suite" is the only “best-in-breed" approach that works – choosing a high-quality platform ensures that every new capability strengthens the whole system.

On top of that, security budgets are under constant pressure. Managing separate vendors for email and network defense means juggling multiple contracts, negotiating different SLAs, and stitching together different support models.

With a single provider for both, procurement and vendor management become far simpler. You deal with one account team, one support channel, and one unified strategy for both environments. If you choose to layer on managed services, you get consistent expertise across your whole security footprint.

Even more importantly, an integrated AI platform sets the stage for growth. Once email and network are under the same roof, adding coverage for other attack surfaces – like cloud or identity – is straightforward. You’re building on the same architecture, not bolting on new point solutions that create more complexity.

Check out the white paper, The Modern Security Stack: Why Your NDR and Email Security Solutions Need to Work Together, to explore these benefits in more depth, with real-world examples and practical steps for unifying your defenses.

[related-resource]

About the author

Blog

September 9, 2025

Unpacking the Salesloft Incident: Insights from Darktrace Observations

Introduction

On August 26, 2025, Google Threat intelligence Group released a report detailing a widespread data theft campaign targeting the sales automation platform Salesloft, via compromised OAuth tokens used by the third-party Drift AI chat agent [1][2]. The attack has been attributed to the threat actor UNC6395 by Google Threat Intelligence and Mandiant [1].

The attack is believed to have begun in early August 2025 and continued through until mid-August 2025 [1], with the threat actor exporting significant volumes of data from multiple Salesforce instances [1]. Then sifting through this data for anything that could be used to compromise the victim’s environments such as access keys, tokens or passwords. This had led to Google Threat Intelligence Group assessing that the primary intent of the threat actor is credential harvesting, and later reporting that it was aware of in excess of 700 potentially impacted organizations [3].

Salesloft previously stated that, based on currently available data, customers that do not integrate with Salesforce are unaffected by this campaign [2]. However, on August 28, Google Threat Intelligence Group announced that “Based on new information identified by GTIG, the scope of this compromise is not exclusive to the Salesforce integration with Salesloft Drift and impacts other integrations” [2]. Google Threat Intelligence has since advised that any and all authentication tokens stored in or connected to the Drift platform be treated as potentially compromised [1].

This campaign demonstrates how attackers are increasingly exploiting trusted Software-as-a-Service (SaaS) integrations as a pathway into enterprise environment.

By abusing these integrations, threat actors were able to exfiltrate sensitive business data at scale, bypassing traditional security controls. Rather than relying on malware or obvious intrusion techniques, the adversaries leveraged legitimate credentials and API traffic that resembled legitimate Salesforce activity to achieve their goals. This type of activity is far harder to detect with conventional security tools, since it blends in with the daily noise of business operations.

The incident underscores the escalating significance of autonomous coverage within SaaS and third-party ecosystems. As businesses increasingly depend on interconnected platforms, visibility gaps become evident that cannot be managed by conventional perimeter and endpoint defenses.

By developing a behavioral comprehension of each organization's distinct use of cloud services, anomalies can be detected, such as logins from unexpected locations, unusually high volumes of API requests, or unusual document activity. These indications serve as an early alert system, even when intruders use legitimate tokens or accounts, enabling security teams to step in before extensive data exfiltration takes place

What happened?

The campaign is believed to have started on August 8, 2025, with malicious activity continuing until at least August 18. The threat actor, tracked as UNC6395, gained access via compromised OAuth tokens associated with Salesloft Drift integrations into Salesforce [1]. Once tokens were obtained, the attackers were able to issue large volumes of Salesforce API requests, exfiltrating sensitive customer and business data.

Initial Intrusion

The attackers first established access by abusing OAuth and refresh tokens from the Drift integration. These tokens gave them persistent access into Salesforce environments without requiring further authentication [1]. To expand their foothold, the threat actor also made use of TruffleHog [4], an open-source secrets scanner, to hunt for additional exposed credentials. Logs later revealed anomalous IAM updates, including unusual UpdateAccessKey activity, which suggested attempts to ensure long-term persistence and control within compromised accounts.

Internal Reconnaissance & Data Exfiltration

Once inside, the adversaries began exploring the Salesforce environments. They ran queries designed to pull sensitive data fields, focusing on objects such as Cases, Accounts, Users, and Opportunities [1]. At the same time, the attackers sifted through this information to identify secrets that could enable access to other systems, including AWS keys and Snowflake credentials [4]. This phase demonstrated the opportunistic nature of the campaign, with the actors looking for any data that could be repurposed for further compromise.

Lateral Movement

Salesloft and Mandiant investigations revealed that the threat actor also created at least one new user account in early September. Although follow-up activity linked to this account was limited, the creation itself suggested a persistence mechanism designed to survive remediation efforts. By maintaining a separate identity, the attackers ensured they could regain access even if their stolen OAuth tokens were revoked.

Accomplishing the mission

The data taken from Salesforce environments included valuable business records, which attackers used to harvest credentials and identify high-value targets. According to Mandiant, once the data was exfiltrated, the actors actively sifted through it to locate sensitive information that could be leveraged in future intrusions [1]. In response, Salesforce and Salesloft revoked OAuth tokens associated with Drift integrations on August 20 [1], a containment measure aimed at cutting off the attackers’ primary access channel and preventing further abuse.

How did the attack bypass the rest of the security stack?

The campaign effectively bypassed security measures by using legitimate credentials and OAuth tokens through the Salesloft Drift integration. This rendered traditional security defenses like endpoint protection and firewalls ineffective, as the activity appeared non-malicious [1]. The attackers blended into normal operations by using common user agents and making queries through the Salesforce API, which made their activity resemble legitimate integrations and scripts. This allowed them to operate undetected in the SaaS environment, exploiting the trust in third-party connections and highlighting the limitations of traditional detection controls.

Darktrace Coverage

Anomalous activities have been identified across multiple Darktrace deployments that appear associated with this campaign. This included two cases on customers based within the United States who had a Salesforce integration, where the pattern of activities was notably similar.

On August 17, Darktrace observed an account belonging to one of these customers logging in from the rare endpoint 208.68.36[.]90, while the user was seen active from another location. This IP is a known indicator of compromise (IoC) reported by open-source intelligence (OSINT) for the campaign [2].

Figure 1: Cyber AI Analyst Incident summarizing the suspicious login seen for the account.

The login event was associated with the application Drift, further connecting the events to this campaign.

Figure 2: Advanced Search logs showing the Application used to login.

Following the login, the actor initiated a high volume of Salesforce API requests using methods such as GET, POST, and DELETE. The GET requests targeted endpoints like /services/data/v57.0/query and /services/data/v57.0/sobjects/Case/describe, where the former is used to retrieve records based on a specific criterion, while the latter provides metadata for the Case object, including field names and data types [5,6].

Subsequently, a POST request to /services/data/v57.0/jobs/query was observed, likely to initiate a Bulk API query job for extracting large volumes of data from the Ingest Job endpoint [7,8].

Finally, a DELETE request to remove an ingestion job batch, possibly an attempt to obscure traces of prior data access or manipulation.

A case on another US-based customer took place a day later, on August 18. This again began with an account logging in from the rare IP 208.68.36[.]90 involving the application Drift. This was followed by Salesforce GET requests targeting the same endpoints as seen in the previous case, and then a POST to the Ingest Job endpoint and finally a DELETE request, all occurring within one minute of the initial suspicious login.

The chain of anomalous behaviors, including a suspicious login and delete request, resulted in Darktrace’s Autonomous Response capability suggesting a ‘Disable user’ action. However, the customer’s deployment configuration required manual confirmation for the action to take effect.

Figure 3: An example model alert for the user, triggered due to an anomalous API DELETE request.

Figure 4: Model Alert Event Log showing various model alerts for the account that ultimately led to an Autonomous Response model being triggered.

Conclusion

In conclusion, this incident underscores the escalating risks of SaaS supply chain attacks, where third-party integrations can become avenues for attacks. It demonstrates how adversaries can exploit legitimate OAuth tokens and API traffic to circumvent traditional defenses. This emphasizes the necessity for constant monitoring of SaaS and cloud activity, beyond just endpoints and networks, while also reinforcing the significance of applying least privilege access and routinely reviewing OAuth permissions in cloud environments. Furthermore, it provides a wider perspective into the evolution of the threat landscape, shifting towards credential and token abuse as opposed to malware-driven compromise.

‍

Credit to Emma Foulger (Global Threat Research Operations Lead), Calum Hall (Technical Content Researcher), Signe Zaharka (Principal Cyber Analyst), Min Kim (Senior Cyber Analyst), Nahisha Nobregas (Senior Cyber Analyst), Priya Thapa (Cyber Analyst)

Appendices

Darktrace Model Detections

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

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

· SaaS / Compliance / Anomalous Salesforce API Event

· SaaS / Unusual Activity / Multiple Unusual SaaS Activities

· Antigena / SaaS / Antigena Unusual Activity Block

· Antigena / SaaS / Antigena Suspicious Source Activity Block

Customers should consider integrating Salesforce with Darktrace where possible. These integrations allow better visibility and correlation to spot unusual behavior and possible threats.