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January 8, 2024

Uncovering CyberCartel Threats in Latin America

Examine the growing threat of cyber cartels in Latin America and learn how to safeguard against their attacks.
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
Alexandra Sentenac
Cyber Analyst
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08
Jan 2024

Introduction

In September 2023, Darktrace published its first Half-Year Threat Report, highlighting Threat Research, Security Operation Center (SOC), model breach, and Cyber AI Analyst analysis and trends across the Darktrace customer fleet. According to Darktrace’s Threat Report, the most observed threat type to affect Darktrace customers during the first half of 2023 was Malware-as-a-Service (Maas). The report highlighted a growing trend where malware strains, specifically in the MaaS ecosystem, “use cross-functional components from other strains as part of their evolution and customization” [1].  

Darktrace’s Threat Research team assessed this ‘Frankenstein’ approach would very likely increase, as shown by the fact that indicators of compromise (IoCs) are becoming “less and less mutually exclusive between malware strains as compromised infrastructure is used by multiple threat actors through access brokers or the “as-a-Service” market” [1].

Darktrace investigated one such threat during the last months of summer 2023, eventually leading to the discovery of CyberCartel-related activity across a significant number of Darktrace customers, especially in Latin America.

CyberCartel Overview and Darktrace Coverage

During a threat hunt, Darktrace’s Threat Research team discovered the download of a binary with a unique Uniform Resource Identifier (URI) pattern. When examining Darktrace’s customer base, it was discovered that binaries with this same URI pattern had been downloaded by a significant number of customer accounts, especially by customers based in Latin America. Although not identical, the targets and tactics, techniques, and procedures (TTPs) resembled those mentioned in an article regarding a botnet called Fenix [2], particularly active in Latin America.

During the Threat Research team’s investigation, nearly 40 potentially affected customer accounts were identified. Darktrace’s global Threat Research team investigates pervasive threats across Darktrace’s customer base daily. This cross-fleet research is based on Darktrace’s anomaly-based detection capability, Darktrace DETECT™, and revolves around technical analysis and contextualization of detection information.

Amid the investigation, further open-source intelligence (OSINT) research revealed that most indicators observed during Darktrace’s investigations were associated to a Latin American threat group named CyberCartel, with a small number of IoCs being associated with the Fenix botnet. While CyberCartel seems to have been active since 2012 and relies on MaaS offerings from well-known malware families, Fenix botnet was allegedly created at the end of last year and “specifically targets users accessing government services, particularly tax-paying individuals in Mexico and Chile” [2].

Both groups share similar targets and TTPs, as well as objectives: installing malware with information-stealing capabilities. In the case of Fenix infections, the compromised device will be added to a botnet and execute tasks given by the attacker(s); while in the case of CyberCartel, it can lead to various types of second-stage info-stealing and Man-in-the-Browser capabilities, including retrieving system information from the compromised device, capturing screenshots of the active browsing tab, and redirecting the user to fraudulent websites such as fake banking sites. According to a report by Metabase Q [2], both groups possibly share command and control (C2) infrastructure, making accurate attribution and assessment of the confidence level for which group was affecting the customer base extremely difficult. Indeed, one of the C2 IPs (104.156.149[.]33) observed on nearly 20 customer accounts during the investigation had OSINT evidence linking it to both CyberCartel and Fenix, as well as another group known to target Mexico called Manipulated Caiman [3] [4] [5].

CyberCartel and Fenix both appear to target banking and governmental services’ users based in Latin America, especially individuals from Mexico and Chile. Target institutions purportedly include tax administration services and several banks operating in the region. Malvertising and phishing campaigns direct users to pages imitating the target institutions’ webpages and prompt the download of a compressed file advertised in a pop-up window. This file claims enhance the user’s security and privacy while navigating the webpage but instead redirects the user to a compromised website hosting a zip file, which itself contains a URL file containing instructions for retrieval of the first stage payload from a remote server.

pop-up window with malicious file
Figure 1: Example of a pop-up window asking the user to download a compressed file allegedly needed to continue navigating the portal. Connections to the domain srlxlpdfmxntetflx[.]com were observed in one account investigated by Darktrace

During their investigations, the Threat Research team observed connections to 100% rare domains (e.g., situacionfiscal[.]online, consultar-rfc[.]online, facturmx[.]info), many of them containing strings such as “mx”, “rcf” and “factur” in their domain names, prior to the downloads of files with the unique URI pattern identified during the aforementioned threat hunting session.

The reference to “rfc” is likely a reference to the Registro Federal de Contribuyentes, a unique registration number issued by Mexico’s tax collection agency, Servicio de Administración Tributaria (SAT). These domains were observed as being 100% rare for the environment and were connected to a few minutes prior to connections to CyberCartel endpoints. Most of the endpoints were newly registered, with creation dates starting from only a few months earlier in the first half of 2023. Interestingly, some of these domains were very similar to legitimate government websites, likely a tactic employed by threat actors to convince users to trust the domains and to bypass security measures.

Figure 2: Screenshot from similarweb[.]com showing the degree of affinity between malicious domains situacionfiscal[.]online and facturmx[.]info and the legitimate Mexican government hostname sat[.]gob[.]mx
Figure 3: Screenshot of the likely source infection website facturmx[.]info taken when visited in a sandbox environment

In other customer networks, connections to mail clients were observed, as well as connections to win-rar[.]com, suggesting an interaction with a compressed file. Connections to legitimate government websites were also detected around the same time in some accounts. Shortly after, the infected devices were detected connecting to 100% rare IP addresses over the HTTP protocol using WebDAV user agents such as Microsoft-WebDAV-MiniRedir/10.0.X and DavCInt. Web Distributed Authoring and Versioning, in its full form, is a legitimate extension to the HTTP protocol that allows users to remotely share, copy, move and edit files hosted on a web server. Both CyberCartel and Fenix botnet reportedly abuse this protocol to retrieve the initial payload via a shortcut link. The use (or abuse) of this protocol allows attackers to evade blocklists and streamline payload distribution. In cases investigated by Darktrace, the use of this protocol was not always considered unusual for the breach device, indicating it also was commonly used for its legitimate purposes.

HTTP methods observed included PROPFIND, GET, and OPTIONS, where a higher proportion of PROPFIND requests were observed. PROPFIND is an HTTP method related to the use of WebDAV that retrieves properties in an exactly defined, machine-readable, XML document (GET responses do not have a define format). Properties are pieces of data that describe the state of a resource, i.e., data about data [7]. They are used in distributed authoring environments to provide for efficient discovery and management of resources.  

Figure 4: Device event log showing a connection to facturmx[.]info followed by a WebDAV connection to the 100% rare IP 172.86.68[.]104

In a number of cases, connections to compromised endpoints were followed by the download of one or more executable files with names following the regex pattern /(yes|4496|[A-Za-z]{8})/(((4496|4545)[A-Za-z]{24})|Herramienta_de_Seguridad_SII).(exe|jse), for example 4496UCJlcqwxvkpXKguWNqNWDivM.exe. PROPFIND and GET HTTP requests for dynamic-link library (DLL) files such as urlmon.dll and netutils.dll were also detected. These are legitimate Windows files that are essential to handle network and internet-related tasks in Windows. Irrespective of whether they had malicious or legitimate signatures, Darktrace DETECT was able to recognize that the download of these files was suspicious with rare external endpoints not previously observed on the respective customer networks.

Figure 5: Advanced Search results showing some of the HTTP requests made by the breach device to a CyberCartel endpoint via PROPFIND, GET, or OPTIONS methods for executable and DLL files

Following Darktrace DETECT’s model breaches, these HTTP connections were investigated by Cyber AI Analyst™. AI Analyst provided a summary and further technical details of these connections, as shown in figure 6.

Figure 6: Cyber AI Analyst incident showing a summary of the event, as well as technical details. The AI investigation process is also detailed

AI Analyst searched for all HTTP connections made by the breach device and found more than 2,500 requests to more than a hundred endpoints for one given device. It then looked for the user agents responsible for these connections and found 15 possible software agents responsible for the HTTP requests, and from these identified a single suspicious software agent, Microsoft-WebDAV-Min-Redir. As mentioned previously, this is a legitimate software, but its use by the breach device was considered unusual by Darktrace’s machine learning technology. By performing analysis on thousands of connections to hundreds of endpoints at machine speed, AI Analyst is able to perform the heavy lifting on behalf of human security teams and then collate its findings in a single summary pane, giving end-users the information needed to assess a given activity and quickly start remediation as needed. This allows security teams and administrators to save precious time and provides unparalleled visibility over any potentially malicious activity on their network.

Following the successful identification of CyberCartel activity by DETECT, Darktrace RESPOND™ is then able to contain suspicious behavior, such as by restricting outgoing traffic or enforcing normal patterns of life on affected devices. This would allow customer security teams extra time to analyze potentially malicious behavior, while leaving the rest of the network free to perform business critical operations. Unfortunately, in the cases of CyberCartel compromises detected by Darktrace, RESPOND was not enabled in autonomous response mode meaning preventative actions had to be applied manually by the customer’s security team after the fact.

Figure 7. Device event log showing connections to 100% rare CyberCartel endpoint 172.86.68[.]194 and subsequent suggested RESPOND actions.

Conclusion

Threat actors targeting high-value entities such as government offices and banks is unfortunately all too commonplace.  In the case of Cyber Cartel, governmental organizations and entities, as well as multiple newspapers in the Latin America, have cautioned users against these malicious campaigns, which have occurred over the past few years [8] [9]. However, attackers continuously update their toolsets and infrastructure, quickly rendering these warnings and known-bad security precautions obsolete. In the case of CyberCartel, the abuse of the legitimate WebDAV protocol to retrieve the initial payload is just one example of this. This method of distribution has also been leveraged by in Bumblebee malware loader’s latest campaign [10]. The abuse of the legitimate WebDAV protocol to retrieve the initial CyberCartel payload outlined in this case is one example among many of threat actors adopting new distribution methods used by others to further their ends.

As threat actors continue to search for new ways of remaining undetected, notably by incorporating legitimate processes into their attack flow and utilizing non-exclusive compromised infrastructure, it is more important than ever to have an understanding of normal network operation in order to detect anomalies that are indicative of an ongoing compromise. Darktrace’s suite of products, including DETECT+RESPOND, is well placed to do just that, with machine-speed analysis, detection, and response helping security teams and administrators keep their digital environments safe from malicious actors.

Credit to: Nahisha Nobregas, SOC Analyst

References

[1] https://darktrace.com/blog/darktrace-half-year-threat-report

[2] https://www.metabaseq.com/fenix-botnet/

[3] https://perception-point.io/blog/manipulated-caiman-the-sophisticated-snare-of-mexicos-banking-predators-technical-edition/

[4] https://www.virustotal.com/gui/ip-address/104.156.149.33/community

[5] https://silent4business.com/tendencias/1

[6] https://www.metabaseq.com/cybercartel/

[7] http://www.webdav.org/specs/rfc2518.html#rfc.section.4.1

[8] https://www.csirt.gob.cl/alertas/8ffr23-01415-01/

[9] https://www.gob.mx/sat/acciones-y-programas/sitios-web-falsos

[10] https://www.bleepingcomputer.com/news/security/bumblebee-malware-returns-in-new-attacks-abusing-webdav-folders/

Appendices  

Darktrace DETECT Model Detections

AI Analyst Incidents:

• Possible HTTP Command and Control

• Suspicious File Download

Model Detections:

• Anomalous Connection / New User Agent to IP Without Hostname

• Device / New User Agent and New IP

• Anomalous File / EXE from Rare External Location

• Multiple EXE from Rare External Locations

• Anomalous File / Script from Rare External Location

List of IoCs

IoC - Type - Description + Confidence

f84bb51de50f19ec803b484311053294fbb3b523 - SHA1 hash - Likely CyberCartel Payload IoCs

4eb564b84aac7a5a898af59ee27b1cb00c99a53d - SHA1 hash - Likely CyberCartel payload

8806639a781d0f63549711d3af0f937ffc87585c - SHA1 hash - Likely CyberCartel payload

9d58441d9d31b5c4011b99482afa210b030ecac4 - SHA1 hash - Possible CyberCartel payload

37da048533548c0ad87881e120b8cf2a77528413 - SHA1 hash - Likely CyberCartel payload

2415fcefaf86a83f1174fa50444be7ea830bb4d1 - SHA1 hash - Likely CyberCartel payload

15a94c7e9b356d0ff3bcee0f0ad885b6cf9c1bb7 - SHA1 hash - Likely CyberCartel payload

cdc5da48fca92329927d9dccf3ed513dd28956af - SHA1 hash - Possible CyberCartel payload

693b869bc9ba78d4f8d415eb7016c566ead839f3 - SHA1 hash - Likely CyberCartel payload

04ce764723eaa75e4ee36b3d5cba77a105383dc5 - SHA1 hash - Possible CyberCartel payload

435834167fd5092905ee084038eee54797f4d23e - SHA1 hash - Possible CyberCartel payload

3341b4f46c2f45b87f95168893a7485e35f825fe - SHA1 hash - Likely CyberCartel payload

f6375a1f954f317e16f24c94507d4b04200c63b9 - SHA1 hash - Likely CyberCartel payload

252efff7f54bd19a5c96bbce0bfaeeecadb3752f - SHA1 hash - Likely CyberCartel payload

8080c94e5add2f6ed20e9866a00f67996f0a61ae - SHA1 hash - Likely CyberCartel payload

c5117cedc275c9d403a533617117be7200a2ed77 - SHA1 hash - Possible CyberCartel payload

19dd866abdaf8bc3c518d1c1166fbf279787fc03 - SHA1 hash - Likely CyberCartel payload

548287c0350d6e3d0e5144e20d0f0ce28661f514 - SHA1 hash - Likely CyberCartel payload

f0478e88c8eefc3fd0a8e01eaeb2704a580f88e6 - SHA1 hash - Possible CyberCartel payload

a9809acef61ca173331e41b28d6abddb64c5f192 - SHA1 hash - Likely CyberCartel payload

be96ec94f8f143127962d7bf4131c228474cd6ac - SHA1 hash -Likely CyberCartel payload

44ef336395c41bf0cecae8b43be59170bed6759d - SHA1 hash - Possible CyberCartel payload

facturmx[.]info - Hostname - Likely CyberCartel infection source

consultar-rfc[.]online - Hostname - Possible CyberCartel infection source

srlxlpdfmxntetflx[.]com - Hostname - Likely CyberCartel infection source

facturmx[.]online - Hostname - Possible CyberCartel infection source

rfcconhomoclave[.]mx - Hostname - Possible CyberCartel infection source

situacionfiscal[.]online - Hostname - Likely CyberCartel infection source

descargafactura[.]club - Hostname - Likely CyberCartel infection source

104.156.149[.]33 - IP - Likely CyberCartel C2 endpoint

172.86.68[.]194 - IP - Likely CyberCartel C2 endpoint

139.162.73[.]58 - IP - Likely CyberCartel C2 endpoint

172.105.24[.]190 - IP - Possible CyberCartel C2 endpoint

MITRE ATT&CK Mapping

Tactic - Technique

Command and Control - Ingress Tool Transfer (T1105)

Command and Control - Web Protocols (T1071.001)

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
Alexandra Sentenac
Cyber Analyst

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December 18, 2025

Why organizations are moving to label-free, behavioral DLP for outbound email

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Why outbound email DLP needs reinventing

In 2025, the global average cost of a data breach fell slightly — but remains substantial at USD 4.44 million (IBM Cost of a Data Breach Report 2025). The headline figure hides a painful reality: many of these breaches stem not from sophisticated hacks, but from simple human error: mis-sent emails, accidental forwarding, or replying with the wrong attachment. Because outbound email is a common channel for sensitive data leaving an organization, the risk posed by everyday mistakes is enormous.

In 2025, 53% of data breaches involved customer PII, making it the most commonly compromised asset (IBM Cost of a Data Breach Report 2025). This makes “protection at the moment of send” essential. A single unintended disclosure can trigger compliance violations, regulatory scrutiny, and erosion of customer trust –consequences that are disproportionate to the marginal human errors that cause them.

Traditional DLP has long attempted to mitigate these impacts, but it relies heavily on perfect labelling and rigid pattern-matching. In reality, data loss rarely presents itself as a neat, well-structured pattern waiting to be caught – it looks like everyday communication, just slightly out of context.

How data loss actually happens

Most data loss comes from frustratingly familiar scenarios. A mistyped name in auto-complete sends sensitive data to the wrong “Alex.” A user forwards a document to a personal Gmail account “just this once.” Someone shares an attachment with a new or unknown correspondent without realizing how sensitive it is.

Traditional, content-centric DLP rarely catches these moments. Labels are missing or wrong. Regexes break the moment the data shifts formats. And static rules can’t interpret the context that actually matters – the sender-recipient relationship, the communication history, or whether this behavior is typical for the user.

It’s the everyday mistakes that hurt the most. The classic example: the Friday 5:58 p.m. mis-send, when auto-complete selects Martin, a former contractor, instead of Marta in Finance.

What traditional DLP approaches offer (and where gaps remain)

Most email DLP today follows two patterns, each useful but incomplete.

  • Policy- and label-centric DLP works when labels are correct — but content is often unlabeled or mislabeled, and maintaining classification adds friction. Gaps appear exactly where users move fastest
  • Rule and signature-based approaches catch known patterns but miss nuance: human error, new workflows, and “unknown unknowns” that don’t match a rule

The takeaway: Protection must combine content + behavior + explainability at send time, without depending on perfect labels.

Your technology primer: The three pillars that make outbound DLP effective

1) Label-free (vs. data classification)

Protects all content, not just what’s labeled. Label-free analysis removes classification overhead and closes gaps from missing or incorrect tags. By evaluating content and context at send time, it also catches misdelivery and other payload-free errors.

  • No labeling burden; no regex/rule maintenance
  • Works when tags are missing, wrong, or stale
  • Detects misdirected sends even when labels look right

2) Behavioral (vs. rules, signatures, threat intelligence)

Understands user behavior, not just static patterns. Behavioral analysis learns what’s normal for each person, surfacing human error and subtle exfiltration that rules can’t. It also incorporates account signals and inbound intel, extending across email and Teams.

  • Flags risk without predefined rules or IOCs
  • Catches misdelivery, unusual contacts, personal forwards, odd timing/volume
  • Blends identity and inbound context across channels

3) Proprietary DSLM (vs. generic LLM)

Optimized for precise, fast, explainable on-send decisions. A DSLM understands email/DLP semantics, avoids generative risks, and stays auditable and privacy-controlled, delivering intelligence reliably without slowing mail flow.

  • Low-latency, on-send enforcement
  • Non-generative for predictable, explainable outcomes
  • Governed model with strong privacy and auditability

The Darktrace approach to DLP

Darktrace / EMAIL – DLP stops misdelivery and sensitive data loss at send time using hold/notify/justify/release actions. It blends behavioral insight with content understanding across 35+ PII categories, protecting both labeled and unlabeled data. Every action is paired with clear explainability: AI narratives show exactly why an email was flagged, supporting analysts and helping end-users learn. Deployment aligns cleanly with existing SOC workflows through mail-flow connectors and optional Microsoft Purview label ingestion, without forcing duplicate policy-building.

Deployment is simple: Microsoft 365 routes outbound mail to Darktrace for real-time, inline decisions without regex or rule-heavy setup.

A buyer’s checklist for DLP solutions

When choosing your DLP solution, you want to be sure that it can deliver precise, explainable protection at the moment it matters – on send – without operational drag.  

To finish, we’ve compiled a handy list of questions you can ask before choosing an outbound DLP solution:

  • Can it operate label free when tags are missing or wrong? 
  • Does it truly learn per user behavior (no shortcuts)? 
  • Is there a domain specific model behind the content understanding (not a generic LLM)? 
  • Does it explain decisions to both analysts and end users? 
  • Will it integrate with your label program and SOC workflows rather than duplicate them? 

For a deep dive into Darktrace’s DLP solution, check out the full solution brief.

[related-resource]

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Carlos Gray
Senior Product Marketing Manager, Email

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December 17, 2025

Beyond MFA: Detecting Adversary-in-the-Middle Attacks and Phishing with Darktrace

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What is an Adversary-in-the-middle (AiTM) attack?

Adversary-in-the-Middle (AiTM) attacks are a sophisticated technique often paired with phishing campaigns to steal user credentials. Unlike traditional phishing, which multi-factor authentication (MFA) increasingly mitigates, AiTM attacks leverage reverse proxy servers to intercept authentication tokens and session cookies. This allows attackers to bypass MFA entirely and hijack active sessions, stealthily maintaining access without repeated logins.

This blog examines a real-world incident detected during a Darktrace customer trial, highlighting how Darktrace / EMAILTM and Darktrace / IDENTITYTM identified the emerging compromise in a customer’s email and software-as-a-service (SaaS) environment, tracked its progression, and could have intervened at critical moments to contain the threat had Darktrace’s Autonomous Response capability been enabled.

What does an AiTM attack look like?

Inbound phishing email

Attacks typically begin with a phishing email, often originating from the compromised account of a known contact like a vendor or business partner. These emails will often contain malicious links or attachments leading to fake login pages designed to spoof legitimate login platforms, like Microsoft 365, designed to harvest user credentials.

Proxy-based credential theft and session hijacking

When a user clicks on a malicious link, they are redirected through an attacker-controlled proxy that impersonates legitimate services.  This proxy forwards login requests to Microsoft, making the login page appear legitimate. After the user successfully completes MFA, the attacker captures credentials and session tokens, enabling full account takeover without the need for reauthentication.

Follow-on attacks

Once inside, attackers will typically establish persistence through the creation of email rules or registering OAuth applications. From there, they often act on their objectives, exfiltrating sensitive data and launching additional business email compromise (BEC) campaigns. These campaigns can include fraudulent payment requests to external contacts or internal phishing designed to compromise more accounts and enable lateral movement across the organization.

Darktrace’s detection of an AiTM attack

At the end of September 2025, Darktrace detected one such example of an AiTM attack on the network of a customer trialling Darktrace / EMAIL and Darktrace / IDENTITY.

In this instance, the first indicator of compromise observed by Darktrace was the creation of a malicious email rule on one of the customer’s Office 365 accounts, suggesting the account had likely already been compromised before Darktrace was deployed for the trial.

Darktrace / IDENTITY observed the account creating a new email rule with a randomly generated name, likely to hide its presence from the legitimate account owner. The rule marked all inbound emails as read and deleted them, while ignoring any existing mail rules on the account. This rule was likely intended to conceal any replies to malicious emails the attacker had sent from the legitimate account owner and to facilitate further phishing attempts.

Darktrace’s detection of the anomalous email rule creation.
Figure 1: Darktrace’s detection of the anomalous email rule creation.

Internal and external phishing

Following the creation of the email rule, Darktrace / EMAIL observed a surge of suspicious activity on the user’s account. The account sent emails with subject lines referencing payment information to over 9,000 different external recipients within just one hour. Darktrace also identified that these emails contained a link to an unusual Google Drive endpoint, embedded in the text “download order and invoice”.

Darkrace’s detection of an unusual surge in outbound emails containing suspicious content, shortly following the creation of a new email rule.
Figure 2: Darkrace’s detection of an unusual surge in outbound emails containing suspicious content, shortly following the creation of a new email rule.
Darktrace / EMAIL’s detection of the compromised account sending over 9,000 external phishing emails, containing an unusual Google Drive link.
Figure 3: Darktrace / EMAIL’s detection of the compromised account sending over 9,000 external phishing emails, containing an unusual Google Drive link.

As Darktrace / EMAIL flagged the message with the ‘Compromise Indicators’ tag (Figure 2), it would have been held automatically if the customer had enabled default Data Loss Prevention (DLP) Action Flows in their email environment, preventing any external phishing attempts.

Figure 4: Darktrace / EMAIL’s preview of the email sent by the offending account.
Figure 4: Darktrace / EMAIL’s preview of the email sent by the offending account.

Darktrace analysis revealed that, after clicking the malicious link in the email, recipients would be redirected to a convincing landing page that closely mimicked the customer’s legitimate branding, including authentic imagery and logos, where prompted to download with a PDF named “invoice”.

Figure 5: Download and login prompts presented to recipients after following the malicious email link, shown here in safe view.

After clicking the “Download” button, users would be prompted to enter their company credentials on a page that was likely a credential-harvesting tool, designed to steal corporate login details and enable further compromise of SaaS and email accounts.

Darktrace’s Response

In this case, Darktrace’s Autonomous Response was not fully enabled across the customer’s email or SaaS environments, allowing the compromise to progress,  as observed by Darktrace here.

Despite this, Darktrace / EMAIL’s successful detection of the malicious Google Drive link in the internal phishing emails prompted it to suggest ‘Lock Link’, as a recommended action for the customer’s security team to manually apply. This action would have automatically placed the malicious link behind a warning or screening page blocking users from visiting it.

Autonomous Response suggesting locking the malicious Google Drive link sent in internal phishing emails.
Figure 6: Autonomous Response suggesting locking the malicious Google Drive link sent in internal phishing emails.

Furthermore, if active in the customer’s SaaS environment, Darktrace would likely have been able to mitigate the threat even earlier, at the point of the first unusual activity: the creation of a new email rule. Mitigative actions would have included forcing the user to log out, terminating any active sessions, and disabling the account.

Conclusion

AiTM attacks represent a significant evolution in credential theft techniques, enabling attackers to bypass MFA and hijack active sessions through reverse proxy infrastructure. In the real-world case we explored, Darktrace’s AI-driven detection identified multiple stages of the attack, from anomalous email rule creation to suspicious internal email activity, demonstrating how Autonomous Response could have contained the threat before escalation.

MFA is a critical security measure, but it is no longer a silver bullet. Attackers are increasingly targeting session tokens rather than passwords, exploiting trusted SaaS environments and internal communications to remain undetected. Behavioral AI provides a vital layer of defense by spotting subtle anomalies that traditional tools often miss

Security teams must move beyond static defenses and embrace adaptive, AI-driven solutions that can detect and respond in real time. Regularly review SaaS configurations, enforce conditional access policies, and deploy technologies that understand “normal” behavior to stop attackers before they succeed.

Credit to David Ison (Cyber Analyst), Bertille Pierron (Solutions Engineer), Ryan Traill (Analyst Content Lead)

Appendices

Models

SaaS / Anomalous New Email Rule

Tactic – Technique – Sub-Technique  

Phishing - T1566

Adversary-in-the-Middle - T1557

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