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January 31, 2024

How Darktrace Defeated SmokeLoader Malware

Read how Darktrace's AI identified and neutralized SmokeLoader malware. Gain insights into their proactive approach to cybersecurity.
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
Patrick Anjos
Senior Cyber Analyst
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31
Jan 2024

What is Loader Malware?

Loader malware is a type of malicious software designed primarily to infiltrate a system and then download and execute additional malicious payloads.

In recent years, loader malware has emerged as a significant threat for organizations worldwide. This trend is expected to continue given the widespread availability of many loader strains within the Malware-as-a-Service (MaaS) marketplace. The MaaS marketplace contains a wide variety of innovative strains which are both affordable, with toolkits ranging from USD 400 to USD 1,650 [1], and continuously improving, aiming to avoid traditional detection mechanisms.

SmokeLoader is one such example of a MaaS strain that has been observed in the wild since 2011 and continues to pose a significant threat to organizations and their security teams.

How does SmokeLoader Malware work?

SmokeLoader’s ability to drop an array of different malware strains onto infected systems, from backdoors, ransomware, cryptominers, password stealers, point-of-sale malware and banking trojans, means its a highly versatile loader that has remained consistently popular among threat actors.

In addition to its versatility, it also exhibits advanced evasion strategies that make it difficult for traditional security solutions to detect and remove, and it is easily distributed via methods like spam emails or malicious file downloads.

Between July and August 2023, Darktrace observed an increasing trend in SmokeLoader compromises across its customer base. The anomaly-based threat detection capabilities of Darktrace, coupled with the autonomous response technology, identified and contained the SmokeLoader infections in their initial stages, preventing attackers from causing further disruption by deploying other malicious software or ransomware.

SmokeLoader Malware Attack Details

PROPagate Injection Technique

SmokeLoader utilizes the PROPagate code injection technique, a less common method that inserts malicious code into existing processes in order to appear legitimate and bypass traditional signature-based security measures [2] [3]. In the case of SmokeLoader, this technique exploits the Windows SetWindowsSubclass function, which is typically used to add or change the behavior of Windows Operation System. By manipulating this function, SmokeLoader can inject its code into other running processes, such as the Internet Explorer. This not only helps to disguise  the malware's activity but also allows attackers to leverage the permissions and capabilities of the infected process.

Obfuscation Methods

SmokeLoader is known to employ several obfuscation techniques to evade the detection and analysis of security teams. The techniques include scrambling portable executable files, encrypting its malicious code, obfuscating API functions and packing, and are intended to make the malware’s code appear harmless or unremarkable to antivirus software. This allows attackers to slip past defenses and execute their malicious activities while remaining undetected.

Infection Vector and Communication

SmokeLoader typically spreads via phishing emails that employ social engineering tactics to convince users to unknowingly download malicious payloads and execute the malware. Once installed on target networks, SmokeLoader acts as a backdoor, allowing attackers to control infected systems and download further malicious payloads from command-and-control (C2) servers. SmokeLoader uses fast flux, a DNS technique utilized by botets whereby IP addresses associated with C2 domains are rapidly changed, making it difficult to trace the source of the attack. This technique also boosts the resilience of attack, as taking down one or two malicious IP addresses will not significantly impact the botnet's operation.

Continuous Evolution

As with many MaaS strains, SmokeLoader is continuously evolving, with its developers regularly adding new features and techniques to increase its effectiveness and evasiveness. This includes new obfuscation methods, injection techniques, and communication protocols. This constant evolution makes SmokeLoader a significant threat and underscores the importance of advanced threat detection and response capabilities solution.

Darktrace’s Coverage of SmokeLoader Attack

Between July and August 2023, Darktrace detected one particular SmokeLoader infection at multiple stages of its kill chain on a customer network. This detection was made possible by Darktrace DETECT’s anomaly-based approach and Self-Learning AI that allows it to identify subtle deviations in device behavior.

One of the key components of this process is the classification of endpoint rarity and determining whether an endpoint is new or unusual for any given network. This classification is applied to various aspects of observed endpoints, such as domains, IP addresses, or hostnames within the network. It thereby plays a vital role in identifying SmokeLoader activity, such as the initial infection vector or C2 communication, which typically involve a device contacting a malicious endpoint associated with SmokeLoader.

The First Signs of Infection SmokeLoader Infection

Beginning in July 2023, Darktrace observed a surge in suspicious activities that were assessed with moderate to high confidence to be associated with SmokeLoader malware.

For example on July 30, a device was observed making a successful HTTPS request to humman[.]art, a domain that had never been seen on the network, and therefore classified as 100% rare by DETECT. During this connection, the device in question received a total of 6.0 KiB of data from the unusual endpoint. Open-source intelligence (OSINT) sources reported with high confidence that this domain was associated with the SmokeLoader C2 botnet.

The device was then detected making an HTTP request to another 100% rare external IP, namely 85.208.139[.]35, using a new user agent. This request contained the URI ‘/DefenUpdate.exe’, suggesting a possible download of an executable (.exe) file. This was corroborated by the total amount of data received in this connection, 4.3 MB. Both the file name and its size suggest that the offending device may have downloaded additional malicious tooling from the SmokeLoader C2 endpoint, such as a trojan or information stealer, as reported on OSINT platforms [4].

Figure 1: Device event log showing the moment when a device made its first connection to a SmokeLoader associated domain, and the use of a new user agent. A few seconds later, the DETECT model “Anomalous Connection / New User Agent to IP Without Hostname” breached.

The observed new user agent, “Mozilla/5.0 (Windows NT 10.0; Win64; x64; Trident/7.0; rv:11.0) like Gecko” was identified as suspicious by Darktrace leading to the “Anomalous Connection / New User Agent to IP Without Hostname” DETECT model breach.

As this specific user agent was associated with the Internet Explorer browser running on Windows 10, it may not have appeared suspicious to traditional security tools. However, Darktrace’s anomaly-based detection allows it to identify and mitigate emerging threats, even those that utilize sophisticated evasion techniques.

This is particularly noteworthy in this case because, as discussed earlier, SmokeLoader is known to inject its malicious code into legitimate processes, like Internet Explorer.

Figure 2: Darktrace detecting the affected device leveraging a new user agent and establishing an anomalous HTTP connection with an external IP, which was 100% rare to the network.

C2 Communication

Darktrace continued to observe the device making repeated connections to the humman[.]art endpoint. Over the next few days. On August 7, the device was observed making unusual POST requests to the endpoint using port 80, breaching the ‘Anomalous Connection / Multiple HTTP POSTs to Rare Hostname’ DETECT model. These observed POST requests were observed over a period of around 10 days and consisted of a pattern of 8 requests, each with a ten-minute interval.

Figure 3: Model Breach Event Log highlighting the Darktrace DETECT model breach ‘Anomalous Connection / Multiple HTTP POSTs to Rare Hostname’.

Upon investigating the details of this activity identified by Darktrace DETECT, a particular pattern was observed in these requests: they used the same user-agent, “Mozilla/5.0 (Windows NT 10.0; Win64; x64; Trident/7.0; rv:11.0) like Gecko”, which was previously detected in the initial breach.

Additionally, they the requests had a constantly changing  eferrer header, possibly using randomly generated domain names for each request. Further examination of the packet capture (PCAP) from these requests revealed that the payload in these POST requests contained an RC4 encrypted string, strongly indicating SmokeLoader C2 activity.

Figure4: Advanced Search results display an unusual pattern in the requests made by the device to the hostname humman[.]art. This pattern shows a constant change in the referrer header for each request, indicating anomalous behavior.
Figure 5: The PCAP shows the payload seen in these POST requests contained an RC4 encrypted string strongly indicating SmokeLoader C2 activity.  

Unfortunately in this case, Darktrace RESPOND was not active on the network meaning that the attack was able to progress through its kill chain. Despite this, the timely alerts and detailed incident insights provided by Darktrace DETECT allowed the customer’s security team to begin their remediation process, implementing blocks on their firewall, thus preventing the SmokeLoader malware from continuing its communication with C2 infrastructure.

Darktrace RESPOND Halting Potential Threats from the Initial Stages of Detection

With Darktrace RESPOND, organizations can move beyond threat detection to proactive defense against emerging threats. RESPOND is designed to halt threats as soon as they are identified by DETECT, preventing them from escalating into full-blown compromises. This is achieved through advanced machine learning and Self-Learning AI that is able to understand  the normal ‘pattern of life’ of customer networks, allowing for swift and accurate threat detection and response.

One pertinent example was seen on July 6, when Darktrace detected a separate SmokeLoader case on a customer network with RESPOND enabled in autonomous response mode. Darktrace DETECT initially identified a string of anomalous activity associated with the download of suspicious executable files, triggering the ‘Anomalous File / Multiple EXE from Rare External Locations’ model to breach.

The device was observed downloading an executable file (‘6523.exe’ and ‘/g.exe’) via HTTP over port 80. These downloads originated from endpoints that had never been seen within the customer’s environment, namely ‘hugersi[.]com’ and ‘45.66.230[.]164’, both of which had strongly been linked to SmokeLoader by OSINT sources, likely indicating the initial infection stage of the attack [5].

Figure 6: This figure illustrates Darktrace DETECT observing a device downloading multiple .exe files from rare endpoints and the associated model breach, ‘Anomalous File / Multiple EXE from Rare External Locations’.

Around the same time, Darktrace also observed the same device downloading an unusual file with a numeric file name. Threat actors often employ this tactic in order to avoid using file name patterns that could easily be recognized and blocked by traditional security measures; by frequently changing file names, malicious executables are more likely to remain undetected.

Figure 7: Graph showing the unusually high number of executable files downloaded by the device during the initial infection stage of the attack. The orange and red circles represent the number of model breaches that the device made during the observed activity related to SmokeLoader infection.
Figure 8: This figure illustrates the moment when Darktrace DETECT identified a suspicious download with a numeric file name.

With Darktrace RESPOND active and enabled in autonomous response mode, the SmokeLoader infection was thwarted in the first instance. RESPOND took swift autonomous action by blocking connections to the suspicious endpoints identified by DETECT, blocking all outgoing traffic, and enforcing a pre-established “pattern of life” on offending devices. By enforcing a patten of life on a device, Darktrace RESPOND ensures that it cannot deviate from its ‘normal’ activity to carry out potentially malicious activity, while allowing the device to continue expected business operations.

Figure 9:  A total of 8 RESPOND actions were applied, including blocking connections to suspicious endpoints and domains associated with SmokeLoader.

In addition to the autonomous mitigative actions taken by RESPOND, this customer also received a Proactive Threat Notification (PTN) informing them of potentially malicious activity on their network. This prompted the Darktrace Security Operations Center (SOC) to investigate and document the incident, allowing the customer’s security team to shift their focus to remediating and removing the threat of SmokeLoader.

Conclusion

Ultimately, Darktrace showcased its ability to detect and contain versatile and evasive strains of loader malware, like SmokeLoader. Despite its adeptness at bypassing conventional security tools by frequently changing its C2 infrastructure, utilizing existing processes to infect malicious code, and obfuscating malicious file and domain names, Darktrace’s anomaly-based approach allowed it to recognize such activity as deviations from expected network behavior, regardless of their apparent legitimacy.

Considering SmokeLoader’s wide array of functions, including C2 communication that could be used to facilitate additional attacks like exfiltration, or even the deployment of information-stealers or ransomware, Darktrace proved to be crucial in safeguarding customer networks. By identifying and mitigating SmokeLoader at the earliest possible stage, Darktrace effectively prevented the compromises from escalating into more damaging and disruptive compromises.

With the threat of loader malware expected to continue growing alongside the boom of the MaaS industry, it is paramount for organizations to adopt proactive security solutions, like Darktrace DETECT+RESPOND, that are able to make intelligent decisions to identify and neutralize sophisticated attacks.

Credit to Patrick Anjos, Senior Cyber Analyst, Justin Torres, Cyber Analyst

Appendices

Darktrace DETECT Model Detections

- Anomalous Connection / New User Agent to IP Without Hostname

- Anomalous Connection / Multiple HTTP POSTs to Rare Hostname

- Anomalous File / Multiple EXE from Rare External Locations

- Anomalous File / Numeric File Download

List of IOCs (IOC / Type / Description + Confidence)

- 85.208.139[.]35 / IP / SmokeLoader C2 Endpoint

- 185.174.137[.]109 / IP / SmokeLoader C2 Endpoint

- 45.66.230[.]164 / IP / SmokeLoader C2 Endpoint

- 91.215.85[.]147 / IP / SmokeLoader C2 Endpoint

- tolilolihul[.]net / Hostname / SmokeLoader C2 Endpoint

- bulimu55t[.]net / Hostname / SmokeLoader C2 Endpoint

- potunulit[.]org / Hostname / SmokeLoader C2 Endpoint

- hugersi[.]com / Hostname / SmokeLoader C2 Endpoint

- human[.]art / Hostname / SmokeLoader C2 Endpoint

- 371b0d5c867c2f33ae270faa14946c77f4b0953 / SHA1 / SmokeLoader Executable

References:

[1] https://bazaar.abuse.ch/sample/d7c395ab2b6ef69210221337ea292e204b0f73fef8840b6e64ab88595eda45b3/#intel

[2] https://malpedia.caad.fkie.fraunhofer.de/details/win.smokeloader

[3] https://www.darkreading.com/cyber-risk/breaking-down-the-propagate-code-injection-attack

[4] https://n1ght-w0lf.github.io/malware%20analysis/smokeloader/

[5] https://therecord.media/surge-in-smokeloader-malware-attacks-targeting-ukrainian-financial-gov-orgs

MITRE ATT&CK Mapping

Model: Anomalous Connection / New User Agent to IP Without Hostname

ID: T1071.001

Sub technique: T1071

Tactic: COMMAND AND CONTROL

Technique Name: Web Protocols

Model: Anomalous Connection / Multiple HTTP POSTs to Rare Hostname

ID: T1185

Sub technique: -

Tactic: COLLECTION

Technique Name: Man in the Browser

ID: T1071.001

Sub technique: T1071

Tactic: COMMAND AND CONTROL

Technique Name: Web Protocols

Model: Anomalous File / Multiple EXE from Rare External Locations

ID: T1189

Sub technique: -

Tactic: INITIAL ACCESS

Technique Name: Drive-by Compromise

ID: T1588.001

Sub technique: - T1588

Tactic: RESOURCE DEVELOPMENT

Technique Name: Malware

Model: Anomalous File / Numeric File Download

ID: T1189

Sub technique: -

Tactic: INITIAL ACCESS

Technique Name: Drive-by Compromise

ID: T1588.001

Sub technique: - T1588

Tactic: RESOURCE DEVELOPMENT

Technique Name: Malware

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
Patrick Anjos
Senior 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

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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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