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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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April 29, 2025

MFA Under Attack: AiTM Phishing Kits Abusing Legitimate Services

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In late 2024 and early 2025, the Darktrace Security Operations Center (SOC) investigated alerts regarding separate cases of Software-as-a-Service (SaaS) account compromises on two customer environments that presented several similarities, suggesting they were part of a wider phishing campaign.

This campaign was found to leverage the project collaboration and note-taking application, Milanote, and the Tycoon 2FA phishing kit.

Legitimate services abused

As highlighted in Darktrace's 2024 Annual Threat Report [1], threat actors are abusing legitimate services, like Milanote, in their phishing campaigns. By leveraging these trusted platforms and domains, malicious actors can bypass traditional security measures, making their phishing emails appear benign and increasing the likelihood of successful attacks.

Darktrace categorizes these senders and platforms as free content senders. These services allow users to send emails containing custom content (e.g., files) from fully validated, fixed service address belonging to legitimate corporations. Although some of these services permit full body and subject customization by attackers, the structure of these emails is generally consistent, making it challenging to differentiate between legitimate and malicious emails.

What is Tycoon 2FA?

Tycoon 2FA is an Adversary-in-the-Middle (AitM) phishing kit, first seen in August 2023 and distributed via the Phishing-as-a-Service (PhaaS) model [2]. It targets multi-factor authentication (MFA) by intercepting credentials and MFA tokens during authentication on fake Microsoft or Google login pages. The attacker captures session cookies after MFA is completed, allowing them to replay the session and access the user account, even if credentials are reset. The rise in MFA use has increased the popularity of AitM phishing kits like Tycoon 2FA and Mamba 2FA, another AiTM phishing kit investigated by Darktrace.

Initial access via phishing email

At the beginning of 2025, Darktrace observed phishing emails leveraging Milanote being sent to multiple internal recipients in an organization. In this attack, the same email was sent to 19 different users, all of which were held by Darktrace.

The subject line of the emails mentioned both a legitimate internal user of the company, the company name, as well as a Milanote board regarding a “new agreement” in German. It is a common social engineering technique to mention urgent matters, such as unpaid invoices, expired passwords, or awaiting voicemails, in the subject line to prompt immediate action from the user. However, this tactic is now widely covered in phishing awareness training, making users more suspicious of such emails. In this case, while the subject mentioned a “new agreement,” likely raising the recipient’s curiosity, the tone remained professional and not overly alarming. Additionally, the mention of a colleague and the standardized language typical of free content sender emails further helped dispel concerns regarding the email.

These emails were sent by the legitimate address support@milanote[.]com and referenced "Milanote" in the personal field of the header but originated from the freemail address “ahnermatternk.ef.od.13@gmail[.]com”. Darktrace / EMAIL recognized that none of the recipients had previously received a file share email from Milanote, making this sender unfamiliar in the customer's email environment

The emails contained several benign links to legitimate Milanote endpoints (including an unsubscribe link) which were not flagged by Darktrace. However, they also included a malicious link designed to direct recipients to a pre-filled credential harvesting page hosted on Milanote, prompting them to register for an account. Despite not blocking the legitimate Milanote links in the same email, Darktrace locked the malicious link, preventing users from visiting the credential harvester.

Credential harvesting page sent to recipients, as seen in. sandbox environment.
Figure 1: Credential harvesting page sent to recipients, as seen in. sandbox environment.

Around one minute later, one recipient received a legitimate email from Milanote confirming their successful account registration, indicating they had accessed the phishing page. This email had a lower anomaly score and was not flagged by Darktrace / EMAIL because, unlike the first email, it did not contain any suspicious links and was a genuine account registration notification. Similarly, in the malicious Milanote email, only the link leading to the phishing page was blocked, while the benign and legitimate Milanote links remained accessible, demonstrating Darktrace’s precise and targeted actioning.

A legitimate and a malicious Milanote email received by one recipient.
Figure 2: A legitimate and a malicious Milanote email received by one recipient.

Around the same time, Darktrace / NETWORK observed the same user’s device making DNS query for the domain name “lrn.ialeahed[.]com” , which has been flagged as a Tycoon 2FA domain [2], suggesting the use of this phishing platform.

Once the user had entered their details in the credential harvester, it is likely that they were presented a document hosted on Milanote that contained the final payload link – likely hidden behind text instructing users to access a “new agreement” document.

External research indicates that the user was likely directed to a Cloudflare Turnstile challenge meant to reroute unwanted traffic, such as automated security scripts and penetration testing tools [2] [3]. After these checks and other background processes are completed, the user is directed to the final landing page. In this case, it was likely a fake login prompt hosted on the attacker’s server, where the user is asked to authenticate to their account using MFA. By burrowing malicious links and files in this manner, threat actors can evade analysis by traditional security email gateways, effectively bypassing their protection.

Darktrace’s analysis of the structure and word content of the phishing emails resulted in an 82% probability score that the email was malicious, and the email further received a 67% phishing inducement score, representing how closely the structure and word content of the emails compared to typical phishing emails.

All these unusual elements triggered multiple alerts in Darktrace / EMAIL, focusing on two main suspicious aspects: a new, unknown sender with no prior correspondence with the recipients or the environment, and the inclusion of a link to a previously unseen file storage solution.

Milanote phishing email as seen within Darktrace / EMAIL.
Figure 3: Milanote phishing email as seen within Darktrace / EMAIL.

After detecting the fifth email, the “Sender Surge” model alert was triggered in Darktrace / EMAIL due to a significant number of recipients being emailed by this new suspicious sender in a short period. These recipients were from various departments across the customer’s organization, including sales, marketing, purchasing, and production. Darktrace / EMAIL determined that the emails were sent to a highly unusual group of internal recipients, further raising doubts about the business legitimacy.

Darktrace / EMAIL suggested actions to contain the attack by holding all Milanote phishing emails back from recipient’s inboxes, except for the detailed email with locked links. However, autonomous actions were not enabled at the time, allowing the initial email to reach recipients' inboxes, providing a brief window for interaction. Unfortunately, during this window, one recipient clicked on the Milanote payload link, leading to the compromise of their account.

SaaS account takeover

About three minutes after the malicious Milanote email was received, Darktrace / IDENTITY detected an unusual login to the email recipient’s SaaS account. The SaaS actor was observed accessing files from their usual location in Germany, while simultaneously, a 100% rare login occurred from a location in the US that had never been seen in the customer’s environment before. This login was also flagged as suspicious by Microsoft 365, triggering a 'Conditional Access Policy' that required MFA authentication, which was successfully completed.

Tycoon 2FA adnimistration panel login page dated from October 2023 [3].
Figure 4: Tycoon 2FA adnimistration panel login page dated from October 2023 [3].

Despite the successful authentication, Darktrace / IDENTITY recognized that the login from this unusual location, coupled with simultaneous activity in another geographically distant location, were highly suspicious. Darktrace went on to observe MFA-validated logins from three separate US-based IP addresses: 89.185.80[.]19, 5.181.3[.]68, and 38.242.7[.]252. Most of the malicious activity was performed from the latter, which is associated with the Hide My Ass (HMA) VPN network [5].

Darktrace’s detection of the suspicious login from the US while the legitimate user was logged in from Germany.
Figure 5: Darktrace’s detection of the suspicious login from the US while the legitimate user was logged in from Germany.
Darktrace’s detection of the suspicious login following successful MFA authentication.
Figure 6: Darktrace’s detection of the suspicious login following successful MFA authentication.

Following this, the malicious actor accessed the user’s inbox and created a new mailbox rule named “GTH” that deleted any incoming email containing the string “milanote” in the subject line or body. Rules like this are a common technique used by attackers to leverage compromised accounts for launching phishing campaigns and concealing replies to phishing emails that might raise suspicions among legitimate account holders. Using legitimate, albeit compromised, accounts to send additional phishing emails enhances the apparent legitimacy of the malicious emails. This tactic has been reported as being used by Tycoon 2FA attackers [4].

The attacker accessed over 140 emails within the legitimate user’s inbox, including both the inbox and the “Sent Items” folder. Notably, the attacker accessed five emails in the “Sent Items” folder and modified their attachments. These emails were mainly related to invoices, suggesting the threat actor may have been looking to hijack those email threads to send fake invoices or replicate previous invoice emails.

Darktrace’s Cyber AI AnalystTM launched autonomous investigations into the individual events surrounding this suspicious activity. It connected these separate events into a single, broad account takeover incident, providing the customer with a clearer view of the ongoing compromise.

Cyber AI Analyst’s detection of unusual SaaS account activities in a single incident.
Figure 7: Cyber AI Analyst’s detection of unusual SaaS account activities in a single incident.
Cyber AI Analyst investigation of suspicious activities performed by the attacker.
Figure 8: Cyber AI Analyst investigation of suspicious activities performed by the attacker.

Darktrace's response

Within three minutes of the first unusual login alert, Darktrace’s Autonomous Response intervened, disabling the compromised user account for two hours.

As the impacted customer was subscribed to the Managed Threat Detection Service, Darktrace’s SOC team investigated the activity further and promptly alerted the customer’s security team. With the user’s account still disabled by Autonomous Response, the attack was contained, allowing the customer’s security team valuable time to investigate and remediate. Within ten minutes of receiving the alert from Darktrace’s SOC, they reset the user’s password, closed all active SaaS sessions, and deleted the malicious email rule. Darktrace’s SOC further supported the customer through the Security Operations Service Support service by providing information about the data accessed and identifying any other affected users.

Autonomous Response actions carried out by Darktrace / IDENTITY to contain the malicious activity
Figure 9: Autonomous Response actions carried out by Darktrace / IDENTITY to contain the malicious activity.

A wider Milanote phishing campaign?

Around a month before this compromise activity, Darktrace alerted another customer to similar activities involving two compromised user accounts. These accounts created new inbox rules named “GFH” and “GVB” to delete all incoming emails containing the string “milanote” in their subject line and/or body.

The phishing emails that led to the compromise of these user accounts were similar to the ones discussed above. Specifically, these emails were sent via the Milanote platform and referenced a “new agreement” (in Spanish) being shared by a colleague. Additionally, the payload link included in the phishing emails showed the same UserPrincipalName (UPN) attribute (i.e., click?upn=u001.qLX9yCzR), which has been seen in other Milanote phishing emails leveraging Tycoon 2FA reported by OSINT sources [6]. Interestingly, in some cases, the email also referenced a “new agreement” in Portuguese, indicating a global campaign.

Based on the similarities in the rule’s naming convention and action, as well as the similarities in the phishing email subjects, it is likely that these were part of the same campaign leveraging Milanote and Tycoon 2FA to compromise user accounts. Since its introduction, the Tycoon 2FA phishing kit has undergone several enhancements to increase its stealth and obfuscation methods, making it harder for security tools to detect. For example, the latest versions contain special source code to obstruct web page analysis by defenders, prevent users from copying meaningful text from the phishing webpages, and disable the right-click menu to prevent offline analysis [4].

Conclusion

Threat actors are continually employing new methods to bypass security detection tools and measures. As highlighted in this blog, even robust security mechanisms like MFA can be compromised using AitM phishing kits. The misuse of legitimate services such as Milanote for malicious purposes can help attackers evade traditional email security solutions by blurring the distinction between legitimate and malicious content.

This is why security tools based on anomaly detection are crucial for defending against such attacks. However, user awareness is equally important. Delays in processing can impact the speed of response, making it essential for users to be informed about these threats.

Appendices

References

[1] https://www.darktrace.com/resources/annual-threat-report-2024

[2] https://www.validin.com/blog/tycoon_2fa_analyzing_and_hunting_phishing-as-a-service_domains

[3] https://blog.sekoia.io/tycoon-2fa-an-in-depth-analysis-of-the-latest-version-of-the-aitm-phishing-kit/#h-iocs-amp-technical-details

[4] https://blog.barracuda.com/2025/01/22/threat-spotlight-tycoon-2fa-phishing-kit

[5] https://spur.us/context/38.242.7.252    

[6] https://any.run/report/5ef1ac94e4c6c1dc35579321c206453aea80d414108f9f77abd2e2b03ffbd658/be5351d9-53c0-470b-8708-ee2e29300e70

Indicators of Compromise (IoCs)

IoC         Type      Description + Probability

89.185.80[.]19 - IP Address - Malicious login

5.181.3[.]68 - IP Address -Malicious login

38.242.7[.]252 - IP Address - Malicious login and new email inbox rule creation -  Hide My Ass VPN

lrn.ialeahed[.]com – Hostname - Likely Tycoon 2FA domain

Darktrace Model Detections

Email alerts

Platforms / Free Content Sender + High Sender Surge

Platforms / Free Content Sender + Sender Surge

Platforms / Free Content Sender + Unknown Initiator

Platforms / Free Content Sender

Platforms / Free Content Sender + First Time Recipient

Unusual / New Sender Surge

Unusual / Sender Surge

Antigena Anomaly / High Antigena Anomaly

Association / Unknown Sender

History / New Sender

Link / High Rarity Link to File Storage

Link/ Link To File Storage

Link / Link to File Storage + Unknown Sender

Link / Low Link Association

Platforms / Free Content Sender + First Time Initiator

Platforms / Free Content Sender + Unknown Initiator + Freemail

Platforms / Free Content Sender Link

Unusual / Anomalous Association

Unusual / Unlikely Recipient Association

IDENTITY

SaaS / Access / Unusual External Source for SaaS Credential Use

SaaS / Compromise / Login from Rare High Risk Endpoint

SaaS / Access / M365 High Risk Level Login

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

SaaS / Access / MailItemsAccessed from Rare Endpoint

SaaS / Unusual Activity / Multiple Unusual SaaS Activities

SaaS / Unusual Activity / Multiple Unusual External Sources For SaaS Credential

SaaS / Compliance / Anomalous New Email Rule

SaaS / Compromise / Unusual Login and New Email Rule

SaaS / Compromise / SaaS Anomaly Following Anomalous Login

Antigena / SaaS / Antigena Suspicious SaaS Activity Block

Antigena / SaaS / Antigena Enhanced Monitoring from SaaS User Block

Antigena / SaaS / Antigena Unusual Activity Block

Antigena / SaaS / Antigena Suspicious SaaS and Email Activity Block

Cyber AI Analyst Incident

Possible Hijack of Office365 Account

MITRE ATT&CK Mapping

Tactic – Technique

DEFENSE EVASION, PERSISTENCE, PRIVILEGE ESCALATION, INITIAL ACCESS - Cloud Accounts

INITIAL ACCESS - Phishing

CREDENTIAL ACCESS - Steal Web Session Cookie

PERSISTENCE - Account Manipulation

PERSISTENCE - Outlook Rules

RESOURCE DEVELOPMENT - Email Accounts

RESOURCE DEVELOPMENT - Compromise Accounts

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About the author
Alexandra Sentenac
Cyber Analyst

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April 29, 2025

The Importance of NDR in Resilient XDR

picture of hands typing on laptop Default blog imageDefault blog image

As threat actors become more adept at targeting and disabling EDR agents, relying solely on endpoint detection leaves critical blind spots.

Network detection and response (NDR) offers the visibility and resilience needed to catch what EDR can’t especially in environments with unmanaged devices or advanced threats that evade local controls.

This blog explores how threat actors can disable or bypass EDR-based XDR solutions and demonstrates how Darktrace’s approach to NDR closes the resulting security gaps with Self-Learning AI that enables autonomous, real-time detection and response.

Threat actors see local security agents as targets

Recent research by security firms has highlighted ‘EDR killers’: tools that deliberately target EDR agents to disable or damage them. These include the known malicious tool EDRKillShifter, the open source EDRSilencer, EDRSandblast and variants of Terminator, and even the legitimate business application HRSword.

The attack surface of any endpoint agent is inevitably large, whether the software is challenged directly, by contesting its local visibility and access mechanisms, or by targeting the Operating System it relies upon. Additionally, threat actors can readily access and analyze EDR tools, and due to their uniformity across environments an exploit proven in a lab setting will likely succeed elsewhere.

Sophos have performed deep research into the EDRShiftKiller tool, which ESET have separately shown became accessible to multiple threat actor groups. Cisco Talos have reported via TheRegister observing significant success rates when an EDR kill was attempted by ransomware actors.

With the local EDR agent silently disabled or evaded, how will the threat be discovered?

What are the limitations of relying solely on EDR?

Cyber attackers will inevitably break through boundary defences, through innovation or trickery or exploiting zero-days. Preventive measures can reduce but not completely stop this. The attackers will always then want to expand beyond their initial access point to achieve persistence and discover and reach high value targets within the business. This is the primary domain of network activity monitoring and NDR, which includes responsibility for securing the many devices that cannot run endpoint agents.

In the insights from a CISA Red Team assessment of a US CNI organization, the Red Team was able to maintain access over the course of months and achieve their target outcomes. The top lesson learned in the report was:

“The assessed organization had insufficient technical controls to prevent and detect malicious activity. The organization relied too heavily on host-based endpoint detection and response (EDR) solutions and did not implement sufficient network layer protections.”

This proves that partial, isolated viewpoints are not sufficient to track and analyze what is fundamentally a connected problem – and without the added visibility and detection capabilities of NDR, any downstream SIEM or MDR services also still have nothing to work with.

Why is network detection & response (NDR) critical?

An effective NDR finds threats that disable or can’t be seen by local security agents and generally operates out-of-band, acquiring data from infrastructure such as traffic mirroring from physical or virtual switches. This means that the security system is extremely inaccessible to a threat actor at any stage.

An advanced NDR such as Darktrace / NETWORK is fully capable of detecting even high-end novel and unknown threats.

Detecting exploitation of Ivanti CS/PS with Darktrace / NETWORK

On January 9th 2025, two new vulnerabilities were disclosed in Ivanti Connect Secure and Policy Secure appliances that were under malicious exploitation. Perimeter devices, like Ivanti VPNs, are designed to keep threat actors out of a network, so it's quite serious when these devices are vulnerable.

An NDR solution is critical because it provides network-wide visibility for detecting lateral movement and threats that an EDR might miss, such as identifying command and control sessions (C2) and data exfiltration, even when hidden within encrypted traffic and which an EDR alone may not detect.

Darktrace initially detected suspicious activity connected with the exploitation of CVE-2025-0282 on December 29, 2024 – 11 days before the public disclosure of the vulnerability, this early detection highlights the benefits of an anomaly-based network detection method.

Throughout the campaign and based on the network telemetry available to Darktrace, a wide range of malicious activities were identified, including the malicious use of administrative credentials, the download of suspicious files, and network scanning in the cases investigated.

Darktrace / NETWORK’s autonomous response capabilities played a critical role in containment by autonomously blocking suspicious connections and enforcing normal behavior patterns. At the same time, Darktrace Cyber AI Analyst™ automatically investigated and correlated the anomalous activity into cohesive incidents, revealing the full scope of the compromise.

This case highlights the importance of real-time, AI-driven network monitoring to detect and disrupt stealthy post-exploitation techniques targeting unmanaged or unprotected systems.

Unlocking adaptive protection for evolving cyber risks

Darktrace / NETWORK uses unique AI engines that learn what is normal behavior for an organization’s entire network, continuously analyzing, mapping and modeling every connection to create a full picture of your devices, identities, connections, and potential attack paths.

With its ability to uncover previously unknown threats as well as detect known threats Darktrace is an essential layer of the security stack. Darktrace has helped secure customers against attacks including 2024 threat actor campaigns against Fortinet’s FortiManager , Palo Alto firewall devices, and more.  

Stay tuned for part II of this series which dives deeper into the differences between NDR types.

Credit to Nathaniel Jones VP, Security & AI Strategy, FCISO & Ashanka Iddya, Senior Director of Product Marketing for their contribution to this blog.

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About the author
Nathaniel Jones
VP, Security & AI Strategy, Field CISO
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