Onomastics Gymnastics: How Darktrace Detects Spoofing and Business Email Compromise in Multi-Name Users
Spanish-language naming conventions complicate identity mapping for spoofing & especially whale-spoofing detection. Darktrace / EMAIL incorporates parsing logic that allows for faithful spoofing detection in conjunction with anomaly detection.
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
Roberto Romeu
Senior SOC Analyst
Share
05
Nov 2024
Note: For privacy reasons, actual surnames and email addresses observed in these incidents below have been replaced with fictitious placeholder names, using the common Spanish names “Fulano” and “Mengano”.
Naming conventions
Modeling names and their variants of members of an organization is a critical component to properly detect if those same names and variants are being spoofed by malicious actors. For many predominantly English-speaking organizations, these variants can largely be captured by variants of a person’s given name (e.g. James-Jimmy-Jim) and a consistent, singular surname or family name (e.g. Smith). Naming conventions, however, are far from universal. This piece will review how Darktrace / EMAIL manages the common naming conventions of much of the Spanish-speaking world, and can use its modeling to create high-fidelity detections of multiple types of spoofing attempts.
A brief summary of the common convention across Spain and much of Spanish-speaking America: most people are given one or two given names (e.g. Roberto, Juan, María, Natalia), and their surnames are the first surname of their father, followed by the first surname of their mother. While there are various exceptions to this norm, the below graphic Wikipedia [1][2] highlights the general rule.
Figure 1: Example Spanish naming convention for father “José García Torres” and mother “María Acosta Gómez” for child “Pablo García Acosta”. If shortened to one surname, the convention holds the child would be referred to as “Pablo García” [1].
Detection of improper name usage
Implicit in the above comment that shortening to one surname follows the convention of using the first surname, shortening to the second surname is often a tell-tale sign of someone unfamiliar with the person or their broader culture. This can be a useful corroborating feature in detecting a spoof attempt – analogous to a spelling error.
In the case of a Spanish customer, this misuse of name shortening contributed to the detection of a spoof attempt trying to solicit a response by impersonating an internal user forwarding information about ‘Data Protection’.
Figure 2: The Cyber AI Analyst summary of the Darktrace / EMAIL detections shows the use of the Gmail sender impersonating Isabel Maria Fulano Mengano, but incorrectly uses the second surname Mengano.
While the limited communication history from the sender and the nature of the text content already marks the mail as suspicious, Darktrace / EMAIL notes the personal name used in the email is similar to a high-value user (‘whale’ to use the terminology of spearphishing). The additional context provided by the detection of the attempted spoof prompted more severe actioning of this email, leading to a ‘Hold’ action instead of a less-severe ‘Unspoof’ action via a banner on the email.
Figure 3: The content summary of the sender showing the ‘Personal’ field of the email being ‘Isabel Mengano’, breaking from the standard name-shortening convention. The additional metrics identify features that might be anomalous about the sender.
Malicious email properly using both surnames
Misusing the name-shortening convention is not the only way that Darktrace / EMAIL can detect spoofing attempts. In the case of another Spanish customer, Darktrace observed a whale impersonation being sent to 230 users with solicitation content, but no links or attachments. Although the name was modeled internally in the “Surname, Given-name” format, Darktrace identified the spoofing attempt targeting a high-value user and took action, blocking the series of emails from reaching end-user inboxes to prevent unsuspecting users from responding.
Figure 4: Cyber AI Analyst summary of a suspicious email. The personal field is visible as ‘juan fulano mengano’, which is consistent with the reverse-order modelled user ‘fulano mengano, juan’. The subject line ‘Urgent Request’ sent to 230 users gives an intuitive indicator of the emails potentially being part of a malicious solicitation campaign.
In Summary: A case of onomastics gymnastics
The variety in valid usage of human language can be a barrier to evaluating when a given text is benign or malicious. Despite this, Darktrace / EMAIL is designed to manage this variety, as exemplified by the detections of two spoofing attempts seen against organizations using the distinct Spanish-speaking world’s common naming convention. The scope of this design as seen in this onomastic context, extends to a wide range of detections surrounding emails and their behavioral anomalies.
Credit to Roberto Romeu (Principal Cyber Analyst), Justin Torres (Senior Cyber Analyst) and Natalia Sánchez Rocafort (Senior Analyst Consultant).
Discover the most advanced cloud-native AI email security solution to protect your domain and brand while preventing phishing, novel social engineering, business email compromise, account takeover, and data loss.
Gain up to 13 days of earlier threat detection and maximize ROI on your current email security
Experience 20-25% more threat blocking power with Darktrace / EMAIL
Stop the 58% of threats bypassing traditional email security
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.
Why Data Classification Isn’t Enough to Prevent Data Loss
In a world of growing data volume and diversity, protecting and keeping track of your organization’s sensitive information is increasingly complex – particularly when 63% of breaches stem from malicious insiders or human error. This blog explores how security teams can achieve visibility beyond the limits of data classification, without adding to the burden of data management.
Email bombing exposed: Darktrace’s email defense in action
Darktrace detected an email bomb attack flooding inboxes with high volumes of messages, uncovering unusual email patterns and subsequent network anomalies.
FedRAMP High-compliant email security protects federal agencies from nation-state attacks
Not only has Darktrace Federal achieved its FedRAMP High Authority to Operate, one of the few cybersecurity vendors to do this, but we have also released Darktrace Commercial Government Cloud High/Email, a FedRAMP High-compliant email security solution for customers using Microsoft Government Community Cloud High.
Marcus Fowler
CEO of Darktrace Federal and SVP of Strategic Engagements and Threats
MFA Under Attack: AiTM Phishing Kits Abusing Legitimate Services
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.
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.
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.
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.
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].
Figure 5: Darktrace’s detection of the suspicious login from the US while the legitimate user was logged in from Germany.
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.
Figure 7: Cyber AI Analyst’s detection of unusual SaaS account activities in a single incident.
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.
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.
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.
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.
.jpg)
![Tycoon 2FA adnimistration panel login page dated from October 2023 [3].](https://cdn.prod.website-files.com/626ff4d25aca2edf4325ff97/6807b3eb07498494e192803a_Screenshot%202025-04-22%20at%208.20.57%E2%80%AFAM.png)
