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April 2, 2024

Darktrace's Investigation of Raspberry Robin Worm

Discover how Darktrace is leading the hunt for Raspberry Robin. Explore early insights and strategies in the battle against cyber threats.
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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02
Apr 2024

Introduction

In the face of increasingly hardened digital infrastructures and skilled security teams, malicious actors are forced to constantly adapt their attack methods, resulting in sophisticated attacks that are designed to evade human detection and bypass traditional network security measures.  

One such example that was recently investigated by Darktrace is Raspberry Robin, a highly evasive worm malware renowned for merging existing and novel techniques, as well as leveraging both physical hardware and software, to establish a foothold within organization’s networks and propagate additional malicious payloads.

What is Raspberry Robin?

Raspberry Robin, also known as ‘QNAP worm’, is a worm malware that was initially discovered at the end of 2023 [1], however, its debut in the threat landscape may have predated this, with Microsoft uncovering malicious artifacts linked to this threat (which it tracks under the name Storm-0856) dating back to 2019 [4]. At the time, little was known regarding Raspberry Robin’s objectives or operators, despite the large number of successful infections worldwide. While the identity of the actors behind Raspberry Robin still remains a mystery, more intelligence has been gathered about the malware and its end goals as it was observed delivering payloads from different malware families.

Who does Raspberry Robin target?

While it was initially reported that Raspberry Robin primarily targeted the technology and manufacturing industries, researchers discovered that the malware had actually targeted multiple sectors [3] [4]. Darktrace’s own investigations echoed this, with Raspberry Robin infections observed across various industries, including public administration, finance, manufacturing, retail education and transportation.

How does Raspberry Robin work?

Initially, it appeared that Raspberry Robin's access to compromised networks had not been utilized to deliver final-stage malware payloads, nor to steal corporate data. This uncertainty led researchers to question whether the actors involved were merely “cybercriminals playing around” or more serious threats [3]. This lack of additional exploitation was indeed peculiar, considering that attackers could easily escalate their attacks, given Raspberry Robin’s ability to bypass User Account Control using legitimate Windows tools [4].

However, at the end of July 2022, some clarity emerged regarding the operators' end goals. Microsoft researchers revealed that the access provided by Raspberry Robin was being utilized by an access broker tracked as DEV-0206 to distribute the FakeUpdates malware downloader [2]. Researchers further discovered malicious activity associated with Evil Corp TTPs (i.e., DEV-0243) [5] and payloads from the Fauppod malware family leveraging Raspberry Robin’s access [8]. This indicates that Raspberry Robin may, in fact, be an initial access broker, utilizing its presence on hundreds of infected networks to distribute additional payloads for paying malware operators. Thus far, Raspberry Robin has been observed distributing payloads linked to FIN11, Clop Gang, BumbleBee, IcedID, and TrueBot on compromised networks [12].

Raspberry Robin’s Continued Evolution

Since it first appeared in the wild, Raspberry Robin has evolved from "being a widely distributed worm with no observed post-infection actions [...] to one of the largest malware distribution platforms currently active" [8]. The fact that Raspberry Robin has become such a prevalent threat is likely due to the continual addition of new features and evasion capabilities to their malware [6] [7].  

Since its emergence, the malware has “changed its communication method and lateral movement” [6] in order to evade signature detections based on threat intelligence and previous versions. Endpoint security vendors commonly describe it as heavily obfuscated malware, employing multiple layers of evasion techniques to hinder detection and analysis. These include for example dropping a fake payload when analyzed in a sandboxed environment and using mixed-case executing commands, likely to avoid case-sensitive string-based detections.  

In more recent campaigns, Raspberry Robin further appears to have added a new distribution method as it was observed being downloaded from archive files sent as attachments using the messaging service Discord [11]. These attachments contained a legitimate and signed Windows executable, often abused by attackers for side-loading, alongside a malicious dynamic-link library (DLL) containing a Raspberry Robin sample.

Another reason for the recent success of the malware may be found in its use of one-day exploits. According to researchers, Raspberry Robin now utilizes several local privilege escalation exploits that had been recently disclosed, even before a proof of concept had been made available [9] [10]. This led cyber security professionals to believe that operators of the malware may have access to an exploit seller [6]. The use of these exploits enhances Raspberry Robin's detection evasion and persistence capabilities, enabling it to propagate on networks undetected.

Darktrace’s Coverage of Raspberry Robin

Through two separate investigations carried out by Darktrace’s Threat Research team, first in late 2022 and then in November 2023, it became evident that Raspberry Robin was capable of integrating new functionalities and tactics, techniques and procedures (TTPs) into its attacks. Darktrace DETECT™ provided full visibility over the evolving campaign activity, allowing for a comparison of the threat across both investigations. Additionally, if Darktrace RESPOND™ was enabled on affected networks, it was able to quickly mitigate and contain emerging activity during the initial stages, thwarting the further escalation of attacks.

Raspberry Robin Initial Infection

The most prevalent initial infection vector appears to be the introduction of an infected external drive, such as a USB stick, containing a malicious .LNK file (i.e., a Windows shortcut file) disguised as a thumb drive or network share. When clicked, the LNK file automatically launches cmd.exe to execute the malicious file stored on the external drive, and msiexec.exe to connect to a Raspberry Robin command-and-control (C2) endpoint and download the main malware component. The whole process leverages legitimate Windows processes and is therefore less likely to raise any alarms from more traditional security solutions. However, Darktrace DETECT was able to identify the use of Msiexec to connect to a rare endpoint as anomalous in every case investigated.

Little is currently known regarding how the external drives are infected and distributed, but it has been reported that affected USB drives had previously been used for printing at printing and copying shops, suggesting that the infection may have originated from such stores [13].

A method as simple as leaving an infected USB on a desk in a public location can be a highly effective social engineering tactic for attackers. Exploiting both curiosity and goodwill, unsuspecting individuals may innocently plug in a found USB, hoping to identify its owner, unaware that they have unwittingly compromised their device.

As Darktrace primarily operates on the network layer, the insertion of a USB endpoint device would not be within its visibility. Nevertheless, Darktrace did observe several instances wherein multiple Microsoft endpoints were contacted by compromised devices prior to the first connection to a Raspberry Robin domain. For example, connections to the URI '/fwlink/?LinkID=252669&clcid=0x409' were observed in multiple customer environments prior to the first Raspberry Robin external connection. This connectivity seems to be related to Windows attempting to retrieve information about installed hardware, such as a printer, and could also be related to the inserting of an external USB drive.

Figure 1: Device Event Log showing an affected device making connections to Microsoft endpoints, prior to contacting the Raspberry Robin C2 endpoint ‘vqdn[.]net’.
Figure 1: Device Event Log showing an affected device making connections to Microsoft endpoints, prior to contacting the Raspberry Robin C2 endpoint ‘vqdn[.]net’.

Raspberry Robin Command-and-Control Activity

In all cases investigated by Darktrace, compromised devices were detected making HTTP GET connections via the unusual port 8080 to Raspberry Robin C2 endpoints using the new user agent 'Windows Installer'.

The C2 hostnames observed were typically short and matched the regex /[a-zA-Z0-9]{2,4}.[a-zA-Z0-9]{2,6}/, and were hosted on various top-level domains (TLD) such as ‘.rocks’, ‘.pm’, and ‘.wf’. On one customer network, Darktrace observed the download of an MSI file from the Raspberry Robin domain ‘wak[.]rocks’. This package contained a heavily protected malicious DLL file whose purpose was unknown at the time.  

However, in September 2022, external researchers revealed that the main purpose of this DLL was to download further payloads and enable lateral movement, persistence and privilege escalation on compromised devices, as well as exfiltrating sensitive information about the device. As worm infections spread through networks automatically, exfiltrating device data is an essential process for threat actor to keep track of which systems have been infected.

On affected networks investigated by Darktrace, compromised devices were observed making C2 connections that contained sensitive device information, including hostnames and credentials, with additional host information likely found within the data packets [12].

Figure 2: Model Breach Event Log displaying the events that triggered the the ‘New User Agent and Suspicious Request Data’ DETECT model breach.
Figure 2: Model Breach Event Log displaying the events that triggered the the ‘New User Agent and Suspicious Request Data’ DETECT model breach.

As for C2 infrastructure, Raspberry Robin leverages compromised Internet of Things (IoT) devices such as QNAP network attached storage (NAS) systems with hijacked DNS settings [13]. NAS devices are data storage servers that provide access to the files they store from anywhere in the world. These features have been abused by Raspberry Robin operators to distribute their malicious payloads, as any uploaded file could be stored and shared easily using NAS features.

However, Darktrace found that QNAP servers are not the only devices being exploited by Raspberry Robin, with DETECT identifying other IoT devices being used as C2 infrastructure, including a Cerio wireless access point in one example. Darktrace recognized that this connection was new to the environment and deemed it as suspicious, especially as it also used new software and an unusual port for the HTTP protocol (i.e., 8080 rather than 80).

In several instances, Darktrace observed Raspberry Robin utilizing TOR exit notes as backup C2 infrastructure, with compromised devices detected connecting to TOR endpoints.

Figure 3: Raspberry Robin C2 endpoint when viewed in a sandbox environment.
Figure 3: Raspberry Robin C2 endpoint when viewed in a sandbox environment.
Figure 4: Raspberry Robin C2 endpoint when viewed in a sandbox environment.
Figure 4: Raspberry Robin C2 endpoint when viewed in a sandbox environment.

Raspberry Robin in 2022 vs 2023

Despite the numerous updates and advancements made to Raspberry Robin between the investigations carried out in 2022 and 2023, Darktrace’s detection of the malware was largely the same.

DETECT models breached during first investigation at the end of 2022:

  • Device / New User Agent
  • Anomalous Server Activity / New User Agent from Internet Facing System
  • Device / New User Agent and New IP
  • Compromise / Suspicious Request Data
  • Compromise / Uncommon Tor Usage
  • Possible Tor Usage

DETECT models breached during second investigation in late 2023:

  • Device / New User Agent and New IP
  • Device / New User Agent and Suspicious Request Data
  • Device / New User Agent
  • Device / Suspicious Domain
  • Possible Tor Usage

Darktrace’s anomaly-based approach to threat detection enabled it to consistently detect the TTPs and IoCs associated with Raspberry Robin across the two investigations, despite the operator’s efforts to make it stealthier and more difficult to analyze.

In the first investigation in late 2022, Darktrace detected affected devices downloading addition executable (.exe) files following connections to the Raspberry Robin C2 endpoint, including a numeric executable file that appeared to be associated with the Vidar information stealer. Considering the advanced evasion techniques and privilege escalation capabilities of Raspberry Robin, early detection is key to prevent the malware from downloading additional malicious payloads.

In one affected customer environment investigated in late 2023, a total of 12 devices were compromised between mid-September and the end of October. As this particular customer did not have Darktrace RESPOND, the Raspberry Robin infection was able to spread through the network unabated until the customer acted upon Darktrace DETECT’s alerts.

Had Darktrace RESPOND been enabled in autonomous response mode, it would have been able to take immediate action following the first observed connection to a Raspberry Robin C2 endpoint, by blocking connections to the suspicious endpoint and enforcing a device’s normal ‘pattern of life’.

By enforcing a pattern of life on an affected device, RESPOND would prevent it from carrying out any activity that deviates from this learned pattern, including connections to new endpoints using new software as was the case in Figure 5, effectively shutting down the attack in the first instance.

Model Breach Event Log showing RESPOND’s actions against connections to Raspberry Robin C2 endpoints.
Figure 5: Model Breach Event Log showing RESPOND’s actions against connections to Raspberry Robin C2 endpoints.

Conclusion

Raspberry Robin is a highly evasive and adaptable worm known to evolve and change its TTPs on a regular basis in order to remain undetected on target networks for as long as possible. Due to its ability to drop additional malware variants onto compromised devices, it is crucial for organizations and their security teams to detect Raspberry Robin infections at the earliest possible stage to prevent the deployment of potentially disruptive secondary attacks.

Despite its continued evolution, Darktrace's detection of Raspberry Robin remained largely unchanged across the two investigations. Rather than relying on previous IoCs or leveraging existing threat intelligence, Darktrace DETECT’s anomaly-based approach allows it to identify emerging compromises by detecting the subtle deviations in a device’s learned behavior that would typically come with a malware compromise.

By detecting the attacks at an early stage, Darktrace gave its customers full visibility over malicious activity occurring on their networks, empowering them to identify affected devices and remove them from their environments. In cases where Darktrace RESPOND was active, it would have been able to take autonomous follow-up action to halt any C2 communication and prevent the download of any additional malicious payloads.  

Credit to Alexandra Sentenac, Cyber Analyst, Trent Kessler, Senior Cyber Analyst, Victoria Baldie, Director of Incident Management

Appendices

Darktrace DETECT Model Coverage

Device / New User Agent and New IP

Device / New User Agent and Suspicious Request Data

Device / New User Agent

Compromise / Possible Tor Usage

Compromise / Uncommon Tor Usage

MITRE ATT&CK Mapping

Tactic - Technique

Command & Control - T1090.003 Multi-hop Proxy

Lateral Movement - T1210 Exploitation of remote services

Exfiltration over C2 Data - T1041 Exfiltration over C2 Channel

Data Obfuscation - T1001 Data Obfuscation

Vulnerability Scanning - T1595.002 Vulnerability Scanning

Non-Standard Port - T1571 Non-Standard Port

Persistence - T1176 Browser Extensions

Initial Access - T1189 Drive By Compromise / T1566.002  Spearphishing Link

Collection - T1185 Man in the browser

List of IoCs

IoC - Type - Description + Confidence

vqdn[.]net - Hostname - C2 Server

mwgq[.]net - Hostname - C2 Server

wak[.]rocks - Hostname - C2 Server

o7car[.]com - Hostname - C2 Server

6t[.]nz - Hostname - C2 Server

fcgz[.]net - Hostname - Possible C2 Server

d0[.]wf - Hostname - C2 Server

e0[.]wf - Hostname - C2 Server

c4z[.]pl - Hostname - C2 Server

5g7[.]at - Hostname - C2 Server

5ap[.]nl - Hostname - C2 Server

4aw[.]ro - Hostname - C2 Server

0j[.]wf - Hostname - C2 Server

f0[.]tel - Hostname - C2 Server

h0[.]pm - Hostname - C2 Server

y0[.]pm - Hostname - C2 Server

5qy[.]ro - Hostname - C2 Server

g3[.]rs - Hostname - C2 Server

5qe8[.]com - Hostname - C2 Server

4j[.]pm - Hostname - C2 Server

m0[.]yt - Hostname - C2 Server

zk4[.]me - Hostname - C2 Server

59.15.11[.]49 - IP address - Likely C2 Server

82.124.243[.]57 - IP address - C2 Server

114.32.120[.]11 - IP address - Likely C2 Server

203.186.28[.]189 - IP address - Likely C2 Server

70.124.238[.]72 - IP address - C2 Server

73.6.9[.]83 - IP address - Likely C2 Server

References

[1] https://redcanary.com/blog/raspberry-robin/  

[2] https://www.bleepingcomputer.com/news/security/microsoft-links-raspberry-robin-malware-to-evil-corp-attacks/

[3] https://7095517.fs1.hubspotusercontent-na1.net/hubfs/7095517/FLINT%202022-016%20-%20QNAP%20worm_%20who%20benefits%20from%20crime%20(1).pdf

[4] https://www.bleepingcomputer.com/news/security/microsoft-finds-raspberry-robin-worm-in-hundreds-of-windows-networks/

[5] https://therecord.media/microsoft-ties-novel-raspberry-robin-malware-to-evil-corp-cybercrime-syndicate

[6] https://securityaffairs.com/158969/malware/raspberry-robin-1-day-exploits.html

[7] https://research.checkpoint.com/2024/raspberry-robin-keeps-riding-the-wave-of-endless-1-days/

[8] https://redmondmag.com/articles/2022/10/28/microsoft-details-threat-actors-leveraging-raspberry-robin-worm.aspx

[9] https://www.bleepingcomputer.com/news/security/raspberry-robin-malware-evolves-with-early-access-to-windows-exploits/

[10] https://www.bleepingcomputer.com/news/security/raspberry-robin-worm-drops-fake-malware-to-confuse-researchers/

[11] https://thehackernews.com/2024/02/raspberry-robin-malware-upgrades-with.html

[12] https://decoded.avast.io/janvojtesek/raspberry-robins-roshtyak-a-little-lesson-in-trickery/

[13] https://blog.bushidotoken.net/2023/05/raspberry-robin-global-usb-malware.html

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.

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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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