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October 3, 2023

Unveiling ViperSoftX: A Darktrace Investigation

Read about the ViperSoftX threat and how Darktrace's innovative detection methods exposed this cyber intrusion and its potential impacts.
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
Zoe Tilsiter
Cyber Analyst
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03
Oct 2023

Fighting Info-Stealing Malware

The escalating threat posed by information-stealing malware designed to harvest and steal the sensitive data of individuals and organizations alike has become a paramount concern for security teams across the threat landscape. In direct response to security teams improving their threat detection and prevention capabilities, threat actors are forced to continually adapt and advance their techniques, striving for greater sophistication to ensure they can achieve the malicious goals.

What is ViperSoftX?

ViperSoftX is an information stealer and Remote Access Trojan (RAT) malware known to steal privileged information such as cryptocurrency wallet addresses and password information stored in browsers and password managers. It is commonly distributed via the download of cracked software from multiple sources such as suspicious domains, torrent downloads, and key generators (keygens) from third-party sites.

ViperSoftX was first observed in the wild in 2020 [1] but more recently, new strains were identified in 2022 and 2023 utilizing more sophisticated detection evasion techniques, making it more difficult for security teams to identify and analyze. This includes using more advanced encryption methods alongside monthly changes to command-and-control servers (C2) [2], using dynamic-link library (DLL) sideloading for execution techiques, and subsequently loading a malicious browser extension upon infection which works as an independent info-stealer named VenomSoftX [3].

Between February and June 2023, Darktrace detected activity related to the VipersoftX and VenomSoftX information stealers on the networks of more than 100 customers across its fleet. Darktrace DETECT™ was able to successfully identify the anomalous network activity surrounding these emerging information stealer infections and bring them to the attention of the customers, while Darktrace RESPOND™, when enabled in autonomous response mode, was able to quickly intervene and shut down malicious downloads and data exfiltration attempts.

ViperSoftX Attack & Darktrace Coverage

In cases of ViperSoftX information stealer activity observed by Darktrace, the initial infection was caused through the download of malicious files from multimedia sites, endpoints of cracked software like Adobe Illustrator, and torrent sites. Endpoint users typically unknowingly download the malware from these endpoints with a sideloaded DLL, posing as legitimate software executables.

Darktrace detected multiple downloads from such multimedia sites and endpoints related to cracked software and BitTorrent, which were likely representative of the initial source of ViperSoftX infection. Darktrace DETECT models such as ‘Anomalous File / Anomalous Octet Stream (No User Agent)’ breached in response to this activity and were brought to the immediate attention of customer security teams. In instances where Darktrace RESPOND was configured in autonomous response mode, Darktrace was able to enforce a pattern of life on offending devices, preventing them from downloading malicious files.  This ensures that devices are limited to conducting only their pre-established expected activit, minimizing disruption to the business whilst targetedly mitigating suspicious file downloads.

The downloads are then extracted, decrypted and begin to run on the device. The now compromised device will then proceed to make external connections to C2 servers to retrieve secondary PowerShell executable. Darktrace identified that infected devices using PowerShell user agents whilst making HTTP GET requests to domain generation algorithm (DGA) ViperSoftX domains represented new, and therefore unusual, activity in a large number of cases.

For example, Darktrace detected one customer device making an HTTP GET request to the endpoint ‘chatgigi2[.]com’, using the PowerShell user agent ‘Mozilla/5.0 (Windows NT; Windows NT 10.0; en-US) WindowsPowerShell/5.1.19041.2364’. This new activity triggered a number of DETECT models, including ‘Anomalous Connection / PowerShell to Rare External’ and ‘Device / New PowerShell User Agent’. Repeated connections to these endpoints also triggered C2 beaconing models including:  

  • Compromise / Agent Beacon (Short Period)
  • Compromise / Agent Beacon (Medium Period)
  • Compromise / Agent Beacon (Long Period)
  • Compromise / Quick and Regular Windows HTTP Beaconing
  • Compromise / SSL or HTTP Beacon

Although a large number of different DGA domains were detected, commonalities in URI formats were seen across affected customers which matched formats previously identified as ViperSoftX C2 communication by open-source intelligence (OSINT), and in other Darktrace investigations.  

URI paths for example, were always of the format /api/, /api/v1/, /v2/, or /v3/, appearing to detail version number, as can be seen in Figure 1.

Figure 1: A Packet Capture (PCAP) taken from Darktrace showing a connection made to a ViperSoftX C2 endpoint containing versioning information, consistent with ViperSoftX pattern of communication.  

Before the secondary PowerShell executables are loaded, ViperSoftX takes a digital fingerprint of the infected machine to gather its configuration details, and exfiltrates them to the C2 server. These include the computer name, username, Operating System (OS), and ensures there are no anti-virus or montoring tools on the device. If no security tool are detected, ViperSoftX then downloads, decrypts and executes the PowerShell file.

Following the GET requests Darktrace observed numerous devices performing HTTP POST requests and beaconing connections to ViperSoftX endpoints with varying globally unique identifiers (GUIDs) within the URIs. These connections represented the exfiltration of device configuration details, such as “anti-virus detected”, “app used”, and “device name”. As seen on another customer’s deployment, this caused the model ‘Anomalous Connection / Multiple HTTP POSTs to Rare Hostname’ to breach, which was also detected by Cyber AI Analyst as seen in Figure 2.

Figure 2: Cyber AI Analyst’s detection of HTTP POSTs being made to apibiling[.]com, a ViperSoftX C2 endpoint.

The malicious PowerShell download then crawls the infected device’s systems and directories looking for any cryptocurrency wallet information and password managers, and exfiltrates harvest data to the C2 infrastructure. The C2 server then provides further browser extensions to Chromium browsers to be downloaded and act as a separate stand-alone information stealer, also known as VenomSoftX.

Similar to the initial download of ViperSoftX, these malicious extensions are disguised as legitimate browser extensions to evade the detection of security teams. VenomSoft X, in turn, searches through and attempts to gather sensitive data from password managers and crypto wallets stored in user browsers. Using this information, VenomSoftX is able to redirect crypocurrency transactions by intercepting and manipulating API requests between the sender and the intended recipient, directing the cryptocurrency to the attacker instead [3].

Following investigation into VipersoftX activity across the customer base, Darktrace notified all affected customers and opened Ask the Expert (ATE) tickets through which customer’s could directly contact the analyst team for support and guidance in the face on the information stealer infection.

How did the attack bypass the rest of the security stack?

As previously mentioned, both the initial download of ViperSoftX and the subsequent download of the VenomX browser extension are disguised as legitimate software or browser downloads. This is a common technique employed by threat actors to infect target devices with malicious software, while going unnoticed by security teams traditional security measures. Furthermore, by masquerading as a legitimate piece of software endpoint users are more likely to trust and therefore download the malware, increasing the likelihood of threat actor’s successfully carrying out their objectives. Additionally, post-infection analysis of shellcode, the executable code used as the payload, is made significantly more difficult by VenomSoftX’s use of bytemapping. Bytemapping prevents the encryption of shellcodes without its corresponding byte map, meaning that the payloads cannot easily be decrypted and analysed by security researchers. [3]

ViperSoftX also takes numerous attempts to prevent their C2 infrastructure from being identified by blocking access to it on browsers, and using multiple DGA domains, thus renderring defunct traditional security measures that rely on threat intelligence and static lists of indicators of compromise (IoCs).

Fortunately for Darktrace customers, Darktrace’s anomaly-based approach to threat detection means that it was able to detect and alert customers to this suspicious activity that may have gone unnoticed by other security tools.

Insights/Conclusion

Faced with the challenge of increasingly competent and capable security teams, malicious actors are having to adopt more sophisticated techniques to successfully compromise target systems and achieve their nefarious goals.

ViperSoftX information stealer makes use of numerous tactics, techniques and procedures (TTPs) designed to fly under the radar and carry out their objectives without being detected. ViperSoftX does not rely on just one information stealing malware, but two with the subsequent injection of the VenomSoftX browser extension, adding an additional layer of sophistication to the informational stealing operation and increasing the potential yield of sensitive data. Furthermore, the use of evasion techniques like disguising malicious file downloads as legitimate software and frequently changing DGA domains means that ViperSoftX is well equipped to infiltrate target systems and exfiltrate confidential information without being detected.

However, the anomaly-based detection capabilities of Darktrace DETECT allows it to identify subtle changes in a device’s behavior, that could be indicative of an emerging compromise, and bring it to the customer’s security team. Darktrace RESPOND is then autonomously able to take action against suspicious activity and shut it down without latency, minimizing disruption to the business and preventing potentially significant financial losses.

Credit to: Zoe Tilsiter, Senior Cyber Analyst, Nathan Lorenzo, Cyber Analyst.

Appendices

References

[1] https://www.fortinet.com/blog/threat-research/vipersoftx-new-javascript-threat

[2] https://www.trendmicro.com/en_us/research/23/d/vipersoftx-updates-encryption-steals-data.html

[3] https://decoded.avast.io/janrubin/vipersoftx-hiding-in-system-logs-and-spreading-venomsoftx/

Darktrace DETECT Model Detections

·       Anomalous File / Anomalous Octet Stream (No User Agent)

·       Anomalous Connection / PowerShell to Rare External

·       Anomalous Connection / Multiple HTTP POSTs to Rare Hostname

·       Anomalous Connection / Lots of New Connections

·       Anomalous Connection / Multiple Failed Connections to Rare Endpoint

·       Anomalous Server Activity / Outgoing from Server

·       Compromise / Large DNS Volume for Suspicious Domain

·       Compromise / Quick and Regular Windows HTTP Beaconing

·       Compromise / Beacon for 4 Days

·       Compromise / Suspicious Beaconing Behaviour

·       Compromise / Large Number of Suspicious Failed Connections

·       Compromise / Large Number of Suspicious Successful Connections

·       Compromise / POST and Beacon to Rare External

·       Compromise / DGA Beacon

·       Compromise / Agent Beacon (Long Period)

·       Compromise / Agent Beacon (Medium Period)

·       Compromise / Agent Beacon (Short Period)

·       Compromise / Fast Beaconing to DGA

·       Compromise / SSL or HTTP Beacon

·       Compromise / Slow Beaconing Activity To External Rare

·       Compromise / Beaconing Activity To External Rare

·       Compromise / Excessive Posts to Root

·       Compromise / Connections with Suspicious DNS

·       Compromise / HTTP Beaconing to Rare Destination

·       Compromise / High Volume of Connections with Beacon Score

·       Compromise / Sustained SSL or HTTP Increase

·       Device / New PowerShell User Agent

·       Device / New User Agent and New IP

Darktrace RESPOND Model Detections

·       Antigena / Network / External Threat / Antigena Suspicious File Block

·       Antigena / Network / External Threat / Antigena File then New Outbound Block

·       Antigena / Network / External Threat / Antigena Watched Domain Block

·       Antigena / Network / Significant Anomaly / Antigena Significant Anomaly from Client Block

·       Antigena / Network / External Threat / Antigena Suspicious Activity Block

·       Antigena / Network / Significant Anomaly / Antigena Breaches Over Time Block

·       Antigena / Network / Insider Threat / Antigena Large Data Volume Outbound Block

·       Antigena / Network / External Threat / Antigena Suspicious File Pattern of Life Block

·       Antigena / Network / Significant Anomaly / Antigena Controlled and Model Breach

List of IoCs

Indicator - Type - Description

ahoravideo-blog[.]com - Hostname - ViperSoftX C2 endpoint

ahoravideo-blog[.]xyz - Hostname - ViperSoftX C2 endpoint

ahoravideo-cdn[.]com - Hostname - ViperSoftX C2 endpoint

ahoravideo-cdn[.]xyz - Hostname - ViperSoftX C2 endpoint

ahoravideo-chat[.]com - Hostname - ViperSoftX C2 endpoint

ahoravideo-chat[.]xyz - Hostname - ViperSoftX C2 endpoint

ahoravideo-endpoint[.]xyz - Hostname - ViperSoftX C2 endpoint

ahoravideo-schnellvpn[.]com - Hostname - ViperSoftX C2 endpoint

ahoravideo-schnellvpn[.]xyz - Hostname - ViperSoftX C2 endpoint

apibilng[.]com - Hostname - ViperSoftX C2 endpoint

arrowlchat[.]com - Hostname - ViperSoftX C2 endpoint

bideo-blog[.]com - Hostname - ViperSoftX C2 endpoint

bideo-blog[.]xyz - Hostname - ViperSoftX C2 endpoint

bideo-cdn[.]com - Hostname - ViperSoftX C2 endpoint

bideo-cdn[.]xyz - Hostname - ViperSoftX C2 endpoint

bideo-chat[.]com - Hostname - ViperSoftX C2 endpoint

bideo-chat[.]xyz - Hostname - ViperSoftX C2 endpoint

bideo-endpoint[.]com - Hostname - ViperSoftX C2 endpoint

bideo-endpoint[.]xyz - Hostname - ViperSoftX C2 endpoint

bideo-schnellvpn[.]com - Hostname - ViperSoftX C2 endpoint

chatgigi2[.]com - Hostname - ViperSoftX C2 endpoint

counter[.]wmail-service[.]com - Hostname - ViperSoftX C2 endpoint

fairu-cdn[.]xyz - Hostname - ViperSoftX C2 endpoint

fairu-chat[.]xyz - Hostname - ViperSoftX C2 endpoint

fairu-endpoint[.]com - Hostname - ViperSoftX C2 endpoint

fairu-schnellvpn[.]com - Hostname - ViperSoftX C2 endpoint

fairu-schnellvpn[.]xyz - Hostname - ViperSoftX C2 endpoint

privatproxy-blog[.]com - Hostname - ViperSoftX C2 endpoint

privatproxy-blog[.]xyz - Hostname - ViperSoftX C2 endpoint

privatproxy-cdn[.]com - Hostname - ViperSoftX C2 endpoint

privatproxy-cdn[.]xyz - Hostname - ViperSoftX C2 endpoint

privatproxy-endpoint[.]xyz - Hostname - ViperSoftX C2 endpoint

privatproxy-schnellvpn[.]com - Hostname - ViperSoftX C2 endpoint

privatproxy-schnellvpn[.]xyz - Hostname - ViperSoftX C2 endpoint

static-cdn-349[.]net - Hostname - ViperSoftX C2 endpoint

wmail-blog[.]com - Hostname - ViperSoftX C2 endpoint

wmail-cdn[.]xyz - Hostname - ViperSoftX C2 endpoint

wmail-chat[.]com - Hostname - ViperSoftX C2 endpoint

wmail-schnellvpn[.]com - Hostname - ViperSoftX C2 endpoint

wmail-schnellvpn[.]xyz - Hostname - ViperSoftX C2 endpoint

Mozilla/5.0 (Windows NT; Windows NT 10.0; en-US) WindowsPowerShell/5.1.19041.2364 - User Agent -PowerShell User Agent

MITRE ATT&CK Mapping

Tactic - Technique - Notes

Command and Control - T1568.002 Dynamic Resolution: Domain Generation Algorithms

Command and Control - T1321 Data Encoding

Credential Access - T1555.005 Credentials from Password Stores: Password Managers

Defense Evasion - T1027 Obfuscated Files or Information

Execution - T1059.001 Command and Scripting Interpreter: PowerShell

Execution - T1204 User Execution T1204.002 Malicious File

Persistence - T1176 Browser Extensions - VenomSoftX specific

Persistence, Privilege Escalation, Defense Evasion - T1574.002 Hijack Execution Flow: DLL Side-Loading

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
Zoe Tilsiter
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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