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

Malware Research Lead

•

May 19, 2026

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May 19, 2026

State of AI Cybersecurity 2026: 77% of security stacks include AI, but trust is lagging

Findings in this blog are taken from Darktrace’s annual State of AI Cybersecurity Report 2026.

AI is a contributing member of nearly every modern cybersecurity team. As we discussed earlier in this blog series, rapid AI adoption is expanding the attack surface in ways that security professionals have never before experienced while also empowering attackers to operate at unprecedented speed and scale. It’s only logical that defenders are harnessing the power of AI to fight back.

After all, AI can help cybersecurity teams spot the subtle signs of novel threats before humans can, investigate events more quickly and thoroughly, and automate response. But although AI has been widely adopted, this technology is also frequently misunderstood, and occasionally viewed with suspicion.

For CISOs, the cybersecurity marketplace can be noisy. Making sense of competing vendors’ claims to distinguish the solutions that truly deliver on AI’s full potential from those that do not isn’t always easy. Without a nuanced understanding of the different types of AI used across the cybersecurity stack, it is difficult to make informed decisions about which vendors to work with or how to gain the most value from their solutions. Many security leaders are turning to Managed Security Service Providers (MSSPs) for guidance and support.

The right kinds of AI in the right places?

Back in 2024, when we first conducted this annual survey, more than a quarter of respondents were only vaguely familiar with generative AI or hadn’t heard of it at all. Today, GenAI plays a role in 77% of security stacks. This percentage marks a rapid increase in both awareness and adoption over a relatively short period of time.

According to security professionals, different types of AI are widely integrated into cybersecurity tooling:

67% report that their organization’s security stack uses supervised machine learning
67% report that theirs uses agentic AI
58% report that theirs uses natural language processing (NLP)
35% report that theirs uses unsupervised machine learning

But their responses suggest that organizations aren’t always using the most valuable types of AI for the most relevant use cases.

Despite all the recent attention AI has gotten, supervised machine learning isn’t new. Cybersecurity vendors have been experimenting with models trained on hand-labeled datasets for over a decade. These systems are fed large numbers of examples of malicious activity – for instance, strains of ransomware – and use these examples to generalize common indicators of maliciousness – such as the TTPs of multiple known ransomware strains – so that the models can identify similar attacks in the future. This approach is more effective than signature-based detection, since it isn’t tied to an individual byte sequence or file hash. However, supervised machine learning models can miss patterns or features outside the training data set. When adversarial behavior shifts, these systems can’t easily pivot.

Unsupervised machine learning, by contrast, can identify key patterns and trends in unlabeled data without human input. This enables it to classify information independently and detect anomalies without needing to be taught about past threats. Unsupervised learning can continuously learn about an environment and adapt in real time.

One key distinction between supervised and unsupervised machine learning is that supervised learning algorithms require periodic updating and re-training, whereas unsupervised machine learning trains itself while it works.

The question of trust

Even as AI moves into the mainstream, security professionals are eyeing it with a mix of enthusiasm and caution. Although 89% say they have good visibility into the reasoning behind AI-generated outputs, 74% are limiting AI’s ability to take autonomous action in their SOC until explainability improves. 86% do not allow AI to take even small remediation actions without human oversight.

This model, commonly known as “human in the loop,” is currently the norm across the industry. It seems like a best-of-both-worlds approach that allows teams to experience the benefits of AI-accelerated response without relinquishing control – or needing to trust an AI system.

Keeping humans somewhat in the loop is essential for getting the best out of AI. Analysts will always need to review alerts, make judgement calls, and set guardrails for AI's behavior. Their input helps AI models better understand what “normal” looks like, improving their accuracy over time.

However, relying on human confirmation has real costs – it delays response, increases the cognitive burden analysts must bear, and creates potential coverage gaps when security teams are overwhelmed or unavailable. The traditional model, in which humans monitor and act on every alert, is no longer workable at scale.

If organizations depend too heavily on in-the-loop humans, they risk recreating the very problem AI is meant to solve: backlogs of alerts waiting for analyst review. Removing the human from the loop can buy back valuable time, which analysts can then invest in building a proactive security posture. They can also focus more closely on the most critical incidents, where human attention is truly needed.

Allowing AI to operate autonomously requires trust in its decision-making. This trust can be built gradually over time, with autonomous operations expanding as trust grows. But it also requires knowledge and understanding of AI — what it is, how it works, and how best to deploy it at enterprise scale.

Looking for help in all the right places

To gain access to these capabilities in a way that’s efficient and scalable, growing numbers of security leaders are looking for outsourced support. In fact, 85% of security professionals prefer to obtain new SOC capabilities in the form of a managed service.

This makes sense: Managed Security Service Providers (MSSPs) can deliver deep, continuously available expertise without the cost and complexity of building an in-house team. Outsourcing also allows organizations to scale security coverage up or down as needs change, stay current with evolving threats and regulatory requirements, and leverage AI-native detection and response without needing to manage the AI tools themselves.

Preferences for MSSP-delivered security operations are particularly strong in the education, energy (87%), and healthcare sectors. This makes sense: all are high-value targets for threat actors, and all tend to have limited cybersecurity budgets, so the need for a partner who can deliver affordable access to expertise at scale is strong. Retailers also voiced a strong preference for MSSP-delivered services. These companies are tasked with managing large volumes of consumer personal and financial data, and with transforming an industry traditionally thought of as a late adopter to a vanguard of cyber defense. Technology companies, too, have a marked preference for SOC capabilities delivered by MSSPs. This may simply be because they understand the complexity of the threat landscape – and the advantages of specialized expertise — so well.

In order to help as many organizations as possible – from major enterprises to small and midmarket companies – benefit from enterprise-grade, AI-native security, Darktrace is making it easier for MSSPs to deliver its technology. The ActiveAI Security Portal introduces an alert dashboard designed to increase the speed and efficiency of alert triage, while a new AI-powered managed email security solution is giving MSSPs an edge in the never-ending fight against advanced phishing attacks – helping partners as well as organizations succeed on the frontlines of cyber defense.

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Explore the full State of AI Cybersecurity 2026 report for deeper insights into how security leaders are responding to AI-driven risks.

Learn more about securing AI in your enterprise.

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May 19, 2026

When Open Source Is Weaponized: Analysis of a Trojanized 7 Zip Installer

Background of the malicious 7-Zip installer, and assessing its Impact

Early in 2026, external researchers disclosed a malicious distribution campaign leveraging a trojanized installer masquerading itself as a legitimate 7‑Zip utility. Evidence suggests the campaign was active as of January 2026, during which victims were served a fake installer from 7zip[.]com, a highly convincing typo-squatted domain impersonating the official 7‑Zip distribution site (7-zip[.]org).

Initial access is typically achieved through social engineering and search‑engine abuse, including YouTube tutorial content that explicitly referenced the impersonated domain as the download source. Notably, several reports observed the installer delivered a modified but functional build of 7‑Zip (7zfm.exe) to reduce suspicion and preserve expected user behavior.

However, the installer also dropped additional payloads, such as Uphero.exe, hero.exe, and hero.dll, which are not part of the legitimate 7‑Zip software package. Once installed and executed, these payloads allow the attacker to establish persistence and configure the infected host as a proxy node under their control. This facilitates malicious activities such as traffic relaying, anonymizing infrastructure, and the delivery of secondary payloads [1] [2].

Overall, this attack illustrates a proxyware-style attack that abuses implicit trust in widely deployed third‑party tools while exploiting unconventional delivery vectors such as instructional media. By closely imitating legitimate software behavior and branding, the threat actors significantly reduced user suspicion and increased the likelihood of widespread, undetected compromise.

Threat overview

Darktrace observed multiple customers affected by the malicious 7‑Zip installer between January 12 and January 22, impacting organizations across the Americas (AMS), Asia‑Pacific & Japan (APJ), and Europe, the Middle East, and Africa (EMEA) regions. The activity targeted customers across various sectors, including Human health and social work activities, Manufacturing, Education, and Information and communication.

The following use case highlights a device on one customer network making external connections associated with malicious 7-Zip update activity observed between January 7 and January 18, 2026. This behavior included connectivity to the malicious domain 7zip[.]com, followed by command-and control (C2) activity involving "smshero"-themed domains, as well as outbound proxy connections over ports 1000 and 1002.

Initial Connectivity to 'update[.]7zip[.]com':

*Figure 1: Initial Beaconing to Young Endpoint alert behavior, involving the known tunnel/proxy endpoint ‘79.127.221[.]47’.*

Starting on January 7, Darktrace / NETWORK detected the device making repeated beaconing connections to the endpoint 79.127.221[.]47 over the destination port 1000. The use of this port aligns with open-source intelligence (OSINT) reporting that hero[.]exe establishes outbound proxy connections via non-standard ports such as 1000 and 1002 [1].

*Figure 2: Darktrace observed TLS beaconing alerts to the known trojanized installer, update[.]7zip[.]com · 98.96.229[.]19, over port 443 on January 7th.*

Later the same day, the device initiated TLS beaconing to the endpoint update.7zip[.]com. This is more than likely a common source of compromise, where victims unknowingly installed a modified build of the tool alongside additional malicious components. The campaign then progressed into the next attack phase, marked by established connectivity to various C2 domains.

Beaconing Activity to "smshero"-themed domains

Darktrace subsequently observed the same infected device connecting to various C2 domains used to retrieve configuration data. As such, these external hostnames were themed around the string “smshero”, for example ‘smshero[.]co’.

*Figure 3: On January 8th, Darktrace observed SSL beaconing to a rare destination which was attributed to a known ‘config/control domain’, nova[.]smshero[.]ai.*

The following day, on January 8, the device exhibited its first connectivity to a "smshero"-themed endpoint, which has since been identified as being associated with rotating C2 servers [1] [3]. Similar beaconing activity continued over the following days, with Darktrace identifying C2 connectivity to update[.]7zip[.]com over port 443, alongside additional connections to “smshero”‑themed endpoints such as zest.hero-sms[.]ai, flux.smshero[.]cc, and glide.smshero[.]cc between January 9 and January 15.

Figure 4: Darktrace later observed continued beaconing alerts over a 4-day interval to additional rare destinations attributed to a known ‘config/control domain’, zest[.]hero-sms[.]ai & glide[.]smshero[.]cc.

Proxied connectivity over destination ports

The primary objective of this campaign is believed to be proxyware, whereby third-party traffic is routed through victim devices to potentially obfuscate malicious activity. Devices were also observed communicating with rare external IPs hosted on Cloudflare and DataCamp Limited ASNs, establishing outbound proxy connections over the non-standard ports 1000 and 1002 [1].

OSINT sources also indicate that connections over these ports leveraged an XOR-encoded protocol (key 0x70) designed to obscure control messages. While the end goal of the campaign remains unclear, residential proxy networks can be abused to evade security rules and facilitate further unauthorized activities, including phishing and malware distribution [1][3].

Specifically, on January 8, Darktrace observed the device engaging in low-and-slow data exfiltration to the IP 79.127.221[.]47, which had first been observed the previous day, over port 1000. Proxyware typically installs an agent that routes third‑party traffic through an end-user’s device, effectively turning it into a residential proxy exit node. This activity likely represents the system actively communicating outbound data to an entity that controls its behavior.

*Figure 5: Darktrace later observed a ‘Low and Slow Exfiltration to IP’ alert, involving the known tunnel/proxy endpoint ‘79.127.221[.]47’.*

Similar activity continued between January 10 and January 18, with Darktrace detecting threat actors attempting to exfiltrate significant volumes of data to 79.127.221[.]47 over destination port 1000.

Throughout the course of this incident, Darktrace’s Cyber AI Analyst launched several autonomous investigations, analyzing each anomalous event and ultimately painting a detailed picture of the attack timeline. These investigations correlated multiple incidents based on Darktrace detections observed between January 7 and January 19. Cyber AI Analyst identified anomalous variables such as repeated connections to unusual endpoints involving data uploads and downloads, with particular emphasis on HTTP and SSL connectivity.

*Figure 6: Darktrace AI Analyst Coverage, showcasing multiple incident events that occurred on January 7th & 8th, highlighting associated malicious 7-zip behaviors.*

*Figure 7: Darktrace AI Analyst Endpoint Details from the given ‘Unusual Repeated Connections’ Incident Event, including the known tunnel/proxy endpoint.*

*Figure 8: Darktrace AI Analyst Coverage, showcasing additional incident events that occurred on January 12th through 18th, highlighting malicious 7-zip behaviors and SSL connectivity.*

Darktrace’s Autonomous Response

At several stages throughout the attack, Darktrace implemented Autonomous Response actions to help contain the suspicious activity as soon as it was identified, providing the customer’s security team with additional time to investigate and remediate. Between January 7 and January 18, Darktrace blocked a wide range of malicious activity, including beaconing connections to unusual endpoints, small data exfiltration attempts, and larger egress efforts, ultimately preventing the attacker from progressing through multiple stages of the attack or achieving their objectives.

*Figure 9: Darktrace Autonomous Response Action Coverage showcasing connection block connection events including various endpoints that occurred on January 7th.*

Figure 10: Darktrace Antigena (Autonomous Response) Model Alert Coverage, showcasing a Antigena Suspicious Activity Block alert occurred on January 10th as a result of the Low and Slow Exfiltration to IP model alert.

Figure 11: Additional Darktrace Antigena (Autonomous Response) Model Alert Coverage, showcasing a Antigena Large Data Volume Outbound Block alert occurred on January 18th as a result of the Uncommon 1 GiB Outbound model alert.

Conclusion

The malicious 7‑Zip installer underscores how attackers continue to weaponize trust in widely used, legitimate software to gain initial access while evading user suspicion. By exploiting familiar and commonly installed services, this type of attack demonstrates that even routine actions, such as installing compression software, can become high‑risk events when defenses or user awareness are insufficient.

This campaign further emphasizes the urgent need for strict software validation and continuous network monitoring. Modern threats no longer rely solely on obscure tools or overtly malicious behavior. Instead, they increasingly blend seamlessly into everyday operations, making detection more challenging.

In this case, Darktrace / NETWORK was able to identify the anomalous activity and Autonomous Response actions in a timely manner, enabling the customer to be quickly notified and providing crucial additional time to investigate further.

In summary, the abuse of a trojanized 7‑Zip installer highlights a concerning shift in modern threat tactics, where trusted and widely deployed tools can serve as primary delivery mechanisms for system compromise. This reality reinforces that proactive detection, continuous monitoring, and strong security awareness are not optional but essential.

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Credit to Justin Torres, Senior Cyber Analyst, David Moreira da Silva, Cyber Analyst, Emma Foulger, Global Threat Research Operations Lead.

Edited by Ryan Traill (Content Manager)