Blog
/
Network
/
September 13, 2023

How Darktrace Stopped Akira Ransomware

Learn how Darktrace is uniquely placed to identify and contain the novel Akira ransomware strain, first observed in March 2023.
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
Manoel Kadja
Cyber Analyst
Default blog imageDefault blog imageDefault blog imageDefault blog imageDefault blog imageDefault blog image
13
Sep 2023

Introduction to Akira Ransomware

In the face of a seemingly never-ending production line of novel ransomware strains, security teams across the threat landscape are continuing to see a myriad of new variants and groups targeting their networks. Naturally, new strains and threat groups present unique challenges to organizations. The use of previously unseen tactics, techniques, and procedures (TTPs) means that threat actors can often completely bypass traditional rule and signature-based security solutions, thus rendering an organization’s digital environment vulnerable to attack.

What is Akira Ransomware?

One such example of a novel ransomware family is Akira, which was first observed in the wild in March 2023. Much like many other strains, Akira is known to target corporate networks worldwide, encrypting sensitive files and demanding huge sums of money to retrieve the data and stop it from being posted online [1].

Key characteristics of Akira Ransomware

  • Targeted Attacks: Focuses on specific industries and organizations, often targeting those with valuable data.
  • Double Extortion Tactics: Employs double extortion by encrypting data and threatening to release it publicly if the ransom is not paid.
  • Advanced Encryption: Utilizes sophisticated encryption algorithms to ensure that data recovery is impossible without the decryption key.
  • Custom Ransom Notes: Delivers personalized ransom notes tailored to the victim, often containing detailed instructions and specific payment demands.
  • Stealth Techniques: Uses advanced evasion techniques to avoid detection by security tools and to remain undetected for extended periods.
  • Fast Encryption Process: Known for its rapid encryption process, minimizing the time window for detection and response by the victim.
  • Frequent Updates: Regularly updates its malware to bypass the latest security defenses and to improve its effectiveness.
  • Professional Communication: Maintains professional and often polite communication with victims to facilitate ransom payments and decryption.

Darktrace AI capabilities detect Akira Ransomware

In late May 2023, Darktrace observed multiple instances of Akira ransomware affecting networks across its customer base. Thanks to its anomaly-based approach to threat detection, Darktrace successfully identified the novel ransomware attacks and provided full visibility over the cyber kill chain, from the initial compromise to the eventual file encryptions and ransom notes. In cases where Darktrace was enabled in autonomous response mode, these attacks were mitigated the early stages of the attack, thus minimizing any disruption or damage to customer networks.

Initial access and privileged escalation

Methods used by Akira ransomware for privileged escalation

The Akira ransomware group typically uses spear-phishing campaigns containing malicious downloads or links as their primary initial access vector; however, they have also been known to use Remote Desktop Protocol (RDP) brute-force attacks to access target networks [2].

While Darktrace did observe the early access activities that are detailed below, it is very likely that the actual initial intrusion happened prior to this, through targeted phishing attacks that fell outside of Darktrace’s purview. The first indicators of compromise (IoCs) that Darktrace observed on customer networks affected by Darktrace were typically unusual RDP sessions, and the use of compromised administrative credentials.

Darktrace detection of initial access and priviledged escalation

On one Darktrace customer’s network (customer A), Darktrace identified a highly privileged credential being used for the first time on an internal server on May 21, 2023. Around a week later, this server was observed establishing RDP connections with multiple internal destination devices via port 3389. Further investigation carried out by the customer revealed that this credential had indeed been compromised. On May 30, Darktrace detected another device scanning internal devices and repeatedly failing to authenticate via Kerberos.

As the customer had integrated Darktrace with Microsoft Defender, their security team received additional cyber threat intelligence from Microsoft which, coupled with the anomaly alerts provided by Darktrace, helped to further contextualize these anomalous events. One specific detail gleaned from this integration was that the anomalous scanning activity and failed authentication attempts were carried out using the compromised administrative credentials mentioned earlier.

By integrating Microsoft Defender with Darktrace, customers can efficiently close security gaps across their digital infrastructure. While Darktrace understands customer environments and provides valuable network-level insights, by integrating with Microsoft Defender, customers can further enrich these insights with endpoint-specific information and activity.

In another customer’s network (customer B), Darktrace detected a device, later observed writing a ransom note, receiving an unusual RDP connection from another internal device. The RDP cookie used during this activity was an administrative RDP cookie that appeared to have been compromised. This device was also observed making multiple connections to the domain, api.playanext[.]com, and using the user agent , AnyDesk/7.1.11, indicating the use of the AnyDesk remote desktop service.

Although this external domain does not appear directly related to Akira ransomware, open-source intelligence (OSINT) found associations with multiple malicious files, and it appeared to be associated with the AnyDesk user agent, AnyDesk/6.0.1 [3]. The connections to this endpoint likely represented the malicious use of AnyDesk to remotely control the customer’s device, rather than Akira command-and-control (C2) infrastructure or payloads. Alternatively, it could be indicative of a spoofing attempt in which the threat actor is attempting to masquerade as legitimate remote desktop service to remain undetected by security tools.

Around the same time, Darktrace observed many devices on customer B’s network making anomalous internal RDP connections and authenticating via Kerberos, NTLM, or SMB using the same administrative credential. These devices were later confirmed to be affected by Akira Ransomware.

Figure 1 shows how Darktrace detected one of those internal devices failing to login via SMB multiple times with a certain credential (indication of a possible SMB/NTLM brute force), before successfully accessing other internal devices via SMB, NTLM and RDP using the likely compromised administrative credential mentioned earlier.

Figure 1: Model Breach Event Log indicating unusual SMB, NTLM and RDP activity with different credentials detected which led to the Darktrace model breaches, "Unusual Admin RDP Session” and “Successful Admin Brute-Force Activity”.

Darktrace models observed for initial access and privilege escalation:

  • Device / Anomalous RDP Followed By Multiple Model Breaches
  • Anomalous Connection / Unusual Admin RDP Session
  • New Admin Credentials on Server
  • Possible SMB/NTLM Brute Force Indicator
  • Unusual Activity / Successful Admin Brute-Force Activity

Internal Reconnaissance and Lateral Movement

The next step Darktrace observed during Akira Ransomware attacks across the customer was internal reconnaissance and lateral movement.

How Akira Ransomware conducts internal reconnaissance

In another customer’s environment (customer C), after authenticating via NTLM using a compromised credential, a domain controller was observed accessing a large amount of SMB shares it had never previously accessed. Darktrace understood that this SMB activity represented a deviation in the device’s expected behavior and recognized that it could be indicative of SMB enumeration. Darktrace observed the device making at least 196 connections to 34 unique internal IPs via port 445. SMB actions read, write, and delete were observed during those connections. This domain controller was also one of many devices on the customer’s network that was received incoming connections from an external endpoint over port 3389 using the RDP protocol, indicating that the devices were likely being remotely controlled from outside the network. While there were no direct OSINT links with this endpoint and Akira ransomware, the domain controller in question was later confirmed to be compromised and played a key role in this phase of the attack.

Moreover, this represents the second IoC that Darktrace observed that had no obvious connection to Akira, likely indicating that Akira actors are establishing entirely new infrastructure to carry out their attacks, or even utilizing newly compromised legitimate infrastructure. As Darktrace adopts an anomaly-based approach to threat detection, it can recognize suspicious activity indicative of an emerging ransomware attack based on its unusualness, rather than having to rely on previously observed IoCs and lists of ‘known-bads’.

Darktrace further observed a flurry of activity related to lateral movement around this time, primarily via SMB writes of suspicious files to other internal destinations. One particular device on customer C’s network was detected transferring multiple executable (.exe) and script files to other internal devices via SMB.

Darktrace recognized that these transfers represented a deviation from the device’s normal SMB activity and may have indicated threat actors were attempting to compromise additional devices via the transfer of malicious software.

Figure 2: Advanced Search results showing 20 files associated with suspicious SMB write activity, amongst them executable files and dynamic link libraries (DLLs).

Darktrace DETECT models observed for internal reconnaissance and lateral movement:

  • Device / RDP Scan
  • Anomalous Connection / SMB Enumeration
  • Anomalous Connection / Possible Share Enumeration Activity
  • Scanning of Multiple Devices (Cyber AI Analyst Incident)
  • Device / Possible SMB/NTLM Reconnaissance
  • Compliance / Incoming Remote Desktop
  • Compliance / Outgoing NTLM Request from DC
  • Unusual Activity / Internal Data Transfer
  • Security Integration / Lateral Movement and Integration Detection
  • Device / Anomalous SMB Followed By Multiple Model Breaches

Ransomware deployment

In the final phase of Akira ransomware attacks detected on Darktrace customer networks, Darktrace identified the file extension “.akira” being added after encryption to a variety of files on the affected network shares, as well as a ransom note titled “akira_readme.txt” being dropped on affected devices.

On customer A’s network, after nearly 9,000 login failures and 2,000 internal connection attempts indicative of scanning activity, one device was detected transferring suspicious files over SMB to other internal devices. The device was then observed connecting to another internal device via SMB and continuing suspicious file activity, such as appending files on network shares with the “.akira” extension, and performing suspicious writes to SMB shares on other internal devices.

Darktrace’s autonomous threat investigator, Cyber AI Analyst™, was able to analyze the multiple events related to this encryption activity and collate them into one AI Analyst incident, presenting a detailed and comprehensive summary of the entire incident within 10 minutes of Darktrace’s initial detection. Rather than simply viewing individual breaches as standalone activity, AI Analyst can identify the individual steps of an ongoing attack to provide complete visibility over emerging compromises and their kill chains. Not only does this bolster the network’s defenses, but the autonomous investigations carried out by AI Analyst also help to save the security team’s time and resources in triaging and monitoring ongoing incidents.

Figure 3: Darktrace Cyber AI Analyst incident correlated multiple model breaches together to show Akira ransomware encryption activity.

In addition to analyzing and compiling Darktrace model breaches, AI Analyst also leveraged the host-level insights provided by Microsoft Defender to enrich its investigation into the encryption event. By using the Security Integration model breaches, AI Analyst can retrieve timestamp and device details from a Defender alert and further investigate any unusual activity surrounding the alert to present a full picture of the suspicious activity.

In customer B’s environment, following the unusual RDP sessions and rare external connections using the AnyDesk user agent, an affected device was later observed writing around 2,000 files named "akira_readme.txt" to multiple internal SMB shares. This represented the malicious actor dropping ransom notes, containing the demands and extortion attempts of the actors.

Figure 4: Model Breach Event Log indicating the ransom note detected on May 12, 2023, which led to the Darktrace DETECT model breach, Anomalous Server Activity / Write to Network Accessible WebRoot.
Figure 5: Packet Capture (PCAP) demonstrating the Akira ransom note captured from the connection details seen in Figure 4.

As a result of this ongoing activity, an Enhanced Monitoring model breach, a high-fidelity detection model type that detects activities that are more likely to be indicative of compromise, was escalated to Darktrace’s Security Operations Center (SOC) who, in turn were able to further investigate and triage this ransomware activity. Customers who have subscribed to Darktrace’s Proactive Threat Notification (PTN) service would receive an alert from the SOC team, advising urgent follow up action.

Darktrace detection models observed during ransomware deployment:

  • Security Integration / Integration Ransomware Incident
  • Security Integration / High Severity Integration Detection
  • Security Integration / Integration Ransomware Detected
  • Device / Suspicious File Writes to Multiple Hidden SMB Shares
  • Compliance / SMB Drive Write
  • Compromise / Ransomware / Suspicious SMB Activity (Proactive Threat Notification Alerted by the Darktrace SOC)
  • Anomalous File / Internal / Additional Extension Appended to SMB File
  • Anomalous File / Internal / Unusual SMB Script Write
  • Compromise / Ransomware / Ransom or Offensive Words Written to SMB
  • Anomalous Server Activity /Write to Network Accessible WebRoot
  • Anomalous Server Activity /Write to Network Accessible WebRoot

Darktrace autonomous response neutralizes Akira Ransomware

When Darktrace is configured in autonomous response mode, it is able to follow up successful threat identifications with instant autonomous actions that stop malicious actors in their tracks and prevent them from achieving their end goals.

In the examples of Darktrace customers affected by Akira Ransomware outlined above, only customer A had autonomous response mode enabled during their ransomware attack. The autonomous response capability of Darktrace helped the customer to minimize disruption to the business through multiple targeted actions on devices affected by ransomware.

One action carried out by Darktrace's Autonomous Respose was to block all on-going traffic from affected devices. In doing so, Darktrace effectively shuts down communications between devices affected by Akira and the malicious infrastructure used by threat actors, preventing the spread of data on the client network or threat actor payloads.

Another crucial response action applied on this customer’s network was combat Akira was to “Enforce a Pattern of Life” on affected devices. This action is designed to prevent devices from performing any activity that would constitute a deviation from their expected behavior, while allowing them to continue their ‘usual’ business operations without causing any disruption.

While the initial intrusion of the attack on customer A’s network likely fell outside of the scope of Darktrace’s visibility, Darktrace was able to minimize the disruption caused by Akira, containing the ransomware and allowing the customer to further investigate and remediate.

Darktrace Autonomous Response model breaches:

  • Antigena / Network / External Threat / Antigena Ransomware Block
  • Antigena / Network / External Threat / Antigena Suspicious Activity Block
  • Antigena / Network / Significant Anomaly / Antigena Enhanced Monitoring from Server Block
  • Antigena / Network / External Threat / Antigena Suspicious Activity Block
  • Antigena / Network / External Threat / Antigena File then New Outbound Block
  • Antigena / Network / Insider Threat / Antigena Unusual Privileged User Activities Block
  • Antigena / Network / Significant Anomaly / Antigena Breaches Over Time Block
  • Antigena / Network / Significant Anomaly / Antigena Significant Anomaly from Client Block
  • Antigena / Network /Insider Threat /Antigena SMB Enumeration Block

Conclusion

The impact of cyber attacks

Novel ransomware strains like Akira Ransomware present a significant challenge to security teams across the globe due to the constant evolution of attack methods and tactics, making it huge a challenge for security teams to stay up to date with the most current threat intelligence.  

Therefore, it is paramount for organizations to adopt a technology designed around an intelligent decision maker able to identify unusual activity that could be indicative of a ransomware attack without depending solely on rules, signatures, or statistic lists of malicious IoCs.

Importance of AI-powered cybersecurity solutions

Darktrace identified Akira ransomware at every stage of the attack’s kill chain on multiple customer networks, even when threat actors were utilizing seemingly legitimate services (or spoofed versions of them) to carry out malicious activity. While this may have gone unnoticed by traditional security tools, Darktrace’s anomaly-based detection enabled it to recognize malicious activity for what it was. When enabled in autonomous response mode, Darktrace is able to follow up initial detections with machine-speed preventative actions to stop the spread of ransomware and minimize the damage caused to customer networks.  

There is no silver bullet to defend against novel cyber-attacks, however Darktrace’s anomaly-based approach to threat detection and autonomous response capabilities are uniquely placed to detect and respond to cyber disruption without latency.

Credit to: Manoel Kadja, Cyber Analyst, Nahisha Nobregas, SOC Analyst.

Appendices

IOC - Type - Description/Confidence

202.175.136[.]197 - External destination IP -Incoming RDP Connection

api.playanext[.]com - External hostname - Possible RDP Host

.akira - File Extension - Akira Ransomware Extension

akira_readme.txt - Text File - Akira Ransom Note

AnyDesk/7.1.11 - User Agent -AnyDesk User Agent

MITRE ATT&CK Mapping

Tactic & Technique

DISCOVERY

T1083 - File and Directory Discovery

T1046 - Network Service Scanning

T1135 - Network Share Discovery

RECONNAISSANCE

T1595.002 - Vulnerability Scanning

CREDENTIAL ACCESS, COLLECTION

T1557.001 - LLMNR/NBT-NS Poisoning and SMB Relay

DEFENSE EVASION, LATERAL MOVEMENT

T1550.002 - Pass the Hash

DEFENSE EVASION, PERSISTENCE, PRIVILEGE ESCALATION, INITIAL ACCESS

T1078 - Valid Accounts

DEFENSE EVASION

T1006 - Direct Volume Access

LATERAL MOVEMENT

T1563.002 - RDP Hijacking

T1021.001 - Remote Desktop Protocol

T1080 - Taint Shared Content

T1021.002 - SMB/Windows Admin Shares

INITIAL ACCESS

T1190 - Exploit Public-Facing Application

T1199 - Trusted Relationship

PERSISTENCE, INITIAL ACCESS

T1133 - External Remote Services

PERSISTENCE

T1505.003 - Web Shell

IMPACT

T1486 - Data Encrypted for Impact

References

[1] https://www.bleepingcomputer.com/news/security/meet-akira-a-new-ransomware-operation-targeting-the-enterprise/

[2] https://www.civilsdaily.com/news/cert-in-warns-against-akira-ransomware/#:~:text=Spread%20Methods%3A%20Akira%20ransomware%20is,Desktop%20connections%20to%20infiltrate%20systems

[3] https://hybrid-analysis.com/sample/0ee9baef94c80647eed30fa463447f000ec1f50a49eecfb71df277a2ca1fe4db?environmentId=100

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
Manoel Kadja
Cyber Analyst

More in this series

No items found.

Blog

/

/

April 29, 2025

MFA Under Attack: AiTM Phishing Kits Abusing Legitimate Services

fingerprintDefault blog imageDefault blog image

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

Continue reading
About the author
Alexandra Sentenac
Cyber Analyst

Blog

/

/

April 29, 2025

The Importance of NDR in Resilient XDR

picture of hands typing on laptop Default blog imageDefault blog image

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

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

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

Threat actors see local security agents as targets

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

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

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

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

What are the limitations of relying solely on EDR?

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

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

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

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

Why is network detection & response (NDR) critical?

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

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

Detecting exploitation of Ivanti CS/PS with Darktrace / NETWORK

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

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

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

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

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

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

Unlocking adaptive protection for evolving cyber risks

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

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

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

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

Continue reading
About the author
Nathaniel Jones
VP, Security & AI Strategy, Field CISO
Your data. Our AI.
Elevate your network security with Darktrace AI