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April 29, 2025

MFA Under Attack: AiTM Phishing Kits Abusing Legitimate Services

Tycoon 2FA uses AiTM phishing and legitimate services to bypass MFA. Darktrace AI stopped it, read the blog to learn how Self-Learning AI detects sophisticated threats.
Inside the SOC
Darktrace cyber analysts are world-class experts in threat intelligence, threat hunting and incident response, and provide 24/7 SOC support to thousands of Darktrace customers around the globe. Inside the SOC is exclusively authored by these experts, providing analysis of cyber incidents and threat trends, based on real-world experience in the field.
Written by
Alexandra Sentenac
Cyber Analyst
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29
Apr 2025

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.

[related-resource]

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

Experts breakdown of Identity Security in the Cloud Era

This white paper discusses the current identity threat landscape and how defenders can adopt new tools to better secure their users and data.

Inside the SOC
Darktrace cyber analysts are world-class experts in threat intelligence, threat hunting and incident response, and provide 24/7 SOC support to thousands of Darktrace customers around the globe. Inside the SOC is exclusively authored by these experts, providing analysis of cyber incidents and threat trends, based on real-world experience in the field.
Written by
Alexandra Sentenac
Cyber Analyst

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July 9, 2025

Defending the Cloud: Stopping Cyber Threats in Azure and AWS with Darktrace

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Real-world intrusions across Azure and AWS

As organizations pursue greater scalability and flexibility, cloud platforms like Microsoft Azure and Amazon Web Services (AWS) have become essential for enabling remote operations and digitalizing corporate environments. However, this shift introduces a new set of security risks, including expanding attack surfaces, misconfigurations, and compromised credentials frequently exploited by threat actors.

This blog dives into three instances of compromise within a Darktrace customer’s Azure and AWS environment which Darktrace.

  1. The first incident took place in early 2024 and involved an attacker compromising a legitimate user account to gain unauthorized access to a customer’s Azure environment.
  2. The other two incidents, taking place in February and March 2025, targeted AWS environments. In these cases, threat actors exfiltrated corporate data, and in one instance, was able to detonate ransomware in a customer’s environment.

Case 1 - Microsoft Azure

Simplified timeline of the attack on a customer’s Azure environment.
Figure 1: Simplified timeline of the attack on a customer’s Azure environment.

In early 2024, Darktrace identified a cloud compromise on the Azure cloud environment of a customer in the Europe, the Middle East and Africa (EMEA) region.

Initial access

In this case, a threat actor gained access to the customer’s cloud environment after stealing access tokens and creating a rogue virtual machine (VM). The malicious actor was found to have stolen access tokens belonging to a third-party external consultant’s account after downloading cracked software.

With these stolen tokens, the attacker was able to authenticate to the customer’s Azure environment and successfully modified a security rule to allow inbound SSH traffic from a specific IP range (i.e., securityRules/AllowCidrBlockSSHInbound). This was likely performed to ensure persistent access to internal cloud resources.

Detection and investigation of the threat

Darktrace / IDENTITY recognized that this activity was highly unusual, triggering the “Repeated Unusual SaaS Resource Creation” alert.

Cyber AI Analyst launched an autonomous investigation into additional suspicious cloud activities occurring around the same time from the same unusual location, correlating the individual events into a broader account hijack incident.

Cyber AI Analyst’s investigation into unusual cloud activity performed by the compromised account.
Figure 2: Cyber AI Analyst’s investigation into unusual cloud activity performed by the compromised account.
Figure 2: Surrounding resource creation events highlighted by Cyber AI Analyst.
Figure 3: Surrounding resource creation events highlighted by Cyber AI Analyst.
Figure 4: Surrounding resource creation events highlighted by Cyber AI Analyst.

“Create resource service limit” events typically indicate the creation or modification of service limits (i.e., quotas) for a specific Azure resource type within a region. Meanwhile, “Registers the Capacity Resource Provider” events refer to the registration of the Microsoft Capacity resource provider within an Azure subscription, responsible for managing capacity-related resources, particularly those related to reservations and service limits. These events suggest that the threat actor was looking to create new cloud resources within the environment.

Around ten minutes later, Darktrace detected the threat actor creating or modifying an Azure disk associated with a virtual machine (VM), suggesting an attempt to create a rogue VM within the environment.

Threat actors can leverage such rogue VMs to hijack computing resources (e.g., by running cryptomining malware), maintain persistent access, move laterally within the cloud environment, communicate with command-and-control (C2) infrastructure, and stealthily deliver and deploy malware.

Persistence

Several weeks later, the compromised account was observed sending an invitation to collaborate to an external free mail (Google Mail) address.

Darktrace deemed this activity as highly anomalous, triggering a compliance alert for the customer to review and investigate further.

The next day, the threat actor further registered new multi-factor authentication (MFA) information. These actions were likely intended to maintain access to the compromised user account. The customer later confirmed this activity by reviewing the corresponding event logs within Darktrace.

Case 2 – Amazon Web Services

Simplified timeline of the attack on a customer’s AWS environment
Figure 5: Simplified timeline of the attack on a customer’s AWS environment

In February 2025, another cloud-based compromised was observed on a UK-based customer subscribed to Darktrace’s Managed Detection and Response (MDR) service.

How the attacker gained access

The threat actor was observed leveraging likely previously compromised credential to access several AWS instances within customer’s Private Cloud environment and collecting and exfiltrating data, likely with the intention of deploying ransomware and holding the data for ransom.

Darktrace alerting to malicious activity

This observed activity triggered a number of alerts in Darktrace, including several high-priority Enhanced Monitoring alerts, which were promptly investigated by Darktrace’s Security Operations Centre (SOC) and raised to the customer’s security team.

The earliest signs of attack observed by Darktrace involved the use of two likely compromised credentials to connect to the customer’s Virtual Private Network (VPN) environment.

Internal reconnaissance

Once inside, the threat actor performed internal reconnaissance activities and staged the Rclone tool “ProgramData\rclone-v1.69.0-windows-amd64.zip”, a command-line program to sync files and directories to and from different cloud storage providers, to an AWS instance whose hostname is associated with a public key infrastructure (PKI) service.

The threat actor was further observed accessing and downloading multiple files hosted on an AWS file server instance, notably finance and investment-related files. This likely represented data gathering prior to exfiltration.

Shortly after, the PKI-related EC2 instance started making SSH connections with the Rclone SSH client “SSH-2.0-rclone/v1.69.0” to a RockHoster Virtual Private Server (VPS) endpoint (193.242.184[.]178), suggesting the threat actor was exfiltrating the gathered data using the Rclone utility they had previously installed. The PKI instance continued to make repeated SSH connections attempts to transfer data to this external destination.

Darktrace’s Autonomous Response

In response to this activity, Darktrace’s Autonomous Response capability intervened, blocking unusual external connectivity to the C2 server via SSH, effectively stopping the exfiltration of data.

This activity was further investigated by Darktrace’s SOC analysts as part of the MDR service. The team elected to extend the autonomously applied actions to ensure the compromise remained contained until the customer could fully remediate the incident.

Continued reconissance

Around the same time, the threat actor continued to conduct network scans using the Nmap tool, operating from both a separate AWS domain controller instance and a newly joined device on the network. These actions were accompanied by further internal data gathering activities, with around 5 GB of data downloaded from an AWS file server.

The two devices involved in reconnaissance activities were investigated and actioned by Darktrace SOC analysts after additional Enhanced Monitoring alerts had triggered.

Lateral movement attempts via RDP connections

Unusual internal RDP connections to a likely AWS printer instance indicated that the threat actor was looking to strengthen their foothold within the environment and/or attempting to pivot to other devices, likely in response to being hindered by Autonomous Response actions.

This triggered multiple scanning, internal data transfer and unusual RDP alerts in Darktrace, as well as additional Autonomous Response actions to block the suspicious activity.

Suspicious outbound SSH communication to known threat infrastructure

Darktrace subsequently observed the AWS printer instance initiating SSH communication with a rare external endpoint associated with the web hosting and VPS provider Host Department (67.217.57[.]252), suggesting that the threat actor was attempting to exfiltrate data to an alternative endpoint after connections to the original destination had been blocked.

Further investigation using open-source intelligence (OSINT) revealed that this IP address had previously been observed in connection with SSH-based data exfiltration activity during an Akira ransomware intrusion [1].

Once again, connections to this IP were blocked by Darktrace’s Autonomous Response and subsequently these blocks were extended by Darktrace’s SOC team.

The above behavior generated multiple Enhanced Monitoring alerts that were investigated by Darktrace SOC analysts as part of the Managed Threat Detection service.

Enhanced Monitoring alerts investigated by SOC analysts as part of the Managed Detection and Response service.
Figure 5: Enhanced Monitoring alerts investigated by SOC analysts as part of the Managed Detection and Response service.

Final containment and collaborative response

Upon investigating the unusual scanning activity, outbound SSH connections, and internal data transfers, Darktrace analysts extended the Autonomous Response actions previously triggered on the compromised devices.

As the threat actor was leveraging these systems for data exfiltration, all outgoing traffic from the affected devices was blocked for an additional 24 hours to provide the customer’s security team with time to investigate and remediate the compromise.

Additional investigative support was provided by Darktrace analysts through the Security Operations Service, after the customer's opened of a ticket related to the unfolding incident.

Simplified timeline of the attack
Figure 8: Simplified timeline of the attack

Around the same time of the compromise in Case 2, Darktrace observed a similar incident on the cloud environment of a different customer.

Initial access

On this occasion, the threat actor appeared to have gained entry into the AWS-based Virtual Private Cloud (VPC) network via a SonicWall SMA 500v EC2 instance allowing inbound traffic on any port.

The instance received HTTPS connections from three rare Vultr VPS endpoints (i.e., 45.32.205[.]52, 207.246.74[.]166, 45.32.90[.]176).

Lateral movement and exfiltration

Around the same time, the EC2 instance started scanning the environment and attempted to pivot to other internal systems via RDP, notably a DC EC2 instance, which also started scanning the network, and another EC2 instance.  

The latter then proceeded to transfer more than 230 GB of data to the rare external GTHost VPS endpoint 23.150.248[.]189, while downloading hundreds of GBs of data over SMB from another EC2 instance.

Cyber AI Analyst incident generated following the unusual scanning and RDP connections from the initial compromised device.
Figure 7: Cyber AI Analyst incident generated following the unusual scanning and RDP connections from the initial compromised device.

The same behavior was replicated across multiple EC2 instances, whereby compromised instances uploaded data over internal RDP connections to other instances, which then started transferring data to the same GTHost VPS endpoint over port 5000, which is typically used for Universal Plug and Play (UPnP).

What Darktrace detected

Darktrace observed the threat actor uploading a total of 718 GB to the external endpoint, after which they detonated ransomware within the compromised VPC networks.

This activity generated nine Enhanced Monitoring alerts in Darktrace, focusing on the scanning and external data activity, with the earliest of those alerts triggering around one hour after the initial intrusion.

Darktrace’s Autonomous Response capability was not configured to act on these devices. Therefore, the malicious activity was not autonomously blocked and escalated to the point of ransomware detonation.

Conclusion

This blog examined three real-world compromises in customer cloud environments each illustrating different stages in the attack lifecycle.

The first case showcased a notable progression from a SaaS compromise to a full cloud intrusion, emphasizing the critical role of anomaly detection when legitimate credentials are abused.

The latter two incidents demonstrated that while early detection is vital, the ability to autonomously block malicious activity at machine speed is often the most effective way to contain threats before they escalate.

Together, these incidents underscore the need for continuous visibility, behavioral analysis, and machine-speed intervention across hybrid environments. Darktrace's AI-driven detection and Autonomous Response capabilities, combined with expert oversight from its Security Operations Center, give defenders the speed and clarity they need to contain threats and reduce operational disruption, before the situation spirals.

Credit to Alexandra Sentenac (Senior Cyber Analyst) and Dylan Evans (Security Research Lead)

References

[1] https://www.virustotal.com/gui/ip-address/67.217.57.252/community

Case 1

Darktrace / IDENTITY model alerts

IaaS / Compliance / Uncommon Azure External User Invite

SaaS / Resource / Repeated Unusual SaaS Resource Creation

IaaS / Compute / Azure Compute Resource Update

Cyber AI Analyst incidents

Possible Unsecured AzureActiveDirectory Resource

Possible Hijack of Office365 Account

Case 2

Darktrace / NETWORK model alerts

Compromise / SSH Beacon

Device / Multiple Lateral Movement Model Alerts

Device / Suspicious SMB Scanning Activity

Device / SMB Lateral Movement

Compliance / SSH to Rare External Destination

Device / Anomalous SMB Followed By Multiple Model Alerts

Device / Anonymous NTLM Logins

Anomalous Connection / SMB Enumeration

Device / New or Uncommon SMB Named Pipe Device / Network Scan

Device / Suspicious Network Scan Activity

Device / New Device with Attack Tools

Device / RDP Scan Device / Attack and Recon Tools

Compliance / High Priority Compliance Model Alert

Compliance / Outgoing NTLM Request from DC

Compromise / Large Number of Suspicious Successful Connections

Device / Large Number of Model Alerts

Anomalous Connection / Multiple Failed Connections to Rare Endpoint

Unusual Activity / Internal Data Transfer

Anomalous Connection / Unusual Internal Connections

Device / Anomalous RDP Followed By Multiple Model Alerts

Unusual Activity / Unusual External Activity

Unusual Activity / Enhanced Unusual External Data Transfer

Unusual Activity / Unusual External Data Transfer

Unusual Activity / Unusual External Data to New Endpoint

Anomalous Connection / Multiple Connections to New External TCP Port

Darktrace / Autonomous Response model alerts

Antigena / Network / Significant Anomaly / Antigena Enhanced Monitoring from Server Block

Antigena / Network / Manual / Quarantine Device

Antigena / MDR / MDR-Quarantined Device

Antigena / MDR / Model Alert on MDR-Actioned Device

Antigena / Network / Significant Anomaly / Antigena Enhanced Monitoring from Client Block

Antigena / Network / Significant Anomaly / Antigena Alerts Over Time Block

Antigena / Network / Insider Threat / Antigena Network Scan Block

Antigena / Network / Significant Anomaly / Antigena Significant Server Anomaly Block

Antigena / Network / Insider Threat / Antigena SMB Enumeration Block

Antigena / Network / Significant Anomaly / Antigena Controlled and Model Alert

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

Antigena / Network / External Threat / Antigena Suspicious Activity Block

Antigena / Network / Insider Threat / Antigena Internal Data Transfer Block

Cyber AI Analyst incidents

Possible Application Layer Reconnaissance Activity

Scanning of Multiple Devices

Unusual Repeated Connections

Unusual External Data Transfer

Case 3

Darktrace / NETWORK model alerts

Unusual Activity / Unusual Large Internal Transfer

Compliance / Incoming Remote Desktop

Unusual Activity / High Volume Server Data Transfer

Unusual Activity / Internal Data Transfer

Anomalous Connection / Unusual Internal Remote Desktop

Anomalous Connection / Unusual Incoming Data Volume

Anomalous Server Activity / Domain Controller Initiated to Client

Device / Large Number of Model Alerts

Anomalous Connection / Possible Flow Device Brute Force

Device / RDP Scan

Device / Suspicious Network Scan Activity

Device / Network Scan

Anomalous Server Activity / Anomalous External Activity from Critical Network Device

Anomalous Connection / Download and Upload

Unusual Activity / Unusual External Data Transfer

Unusual Activity / High Volume Client Data Transfer

Unusual Activity / Unusual External Activity

Anomalous Connection / Uncommon 1 GiB Outbound

Device / Increased External Connectivity

Compromise / Large Number of Suspicious Successful Connections

Anomalous Connection / Data Sent to Rare Domain

Anomalous Connection / Low and Slow Exfiltration to IP

Unusual Activity / Enhanced Unusual External Data Transfer

Anomalous Connection / Multiple Connections to New External TCP Port

Anomalous Server Activity / Outgoing from Server

Anomalous Connection / Multiple Connections to New External UDP Port

Anomalous Connection / Possible Data Staging and External Upload

Unusual Activity / Unusual External Data to New Endpoint

Device / Large Number of Model Alerts from Critical Network Device

Compliance / External Windows Communications

Anomalous Connection / Unusual Internal Connections

Cyber AI Analyst incidents

Scanning of Multiple Devices

Extensive Unusual RDP Connections

MITRE ATT&CK mapping

(Technique name – Tactic ID)

Case 1

Defense Evasion - Modify Cloud Compute Infrastructure: Create Cloud Instance

Persistence – Account Manipulation

Case 2

Initial Access - External Remote Services

Execution - Inter-Process Communication

Persistence - External Remote Services

Discovery - System Network Connections Discovery

Discovery - Network Service Discovery

Discovery - Network Share Discovery

Lateral Movement - Remote Desktop Protocol

Lateral Movement - Remote Services: SMB/Windows Admin Shares

Collection - Data from Network Shared Drive

Command and Control - Protocol Tunneling

Exfiltration - Exfiltration Over Asymmetric Encrypted Non-C2 Protocol

Case 3

Initial Access - Exploit Public-Facing Application

Discovery - Remote System Discovery

Discovery - Network Service Discovery

Lateral Movement - Remote Services

Lateral Movement - Remote Desktop Protocol  

Collection - Data from Network Shared Drive

Collection - Data Staged: Remote Data Staging

Exfiltration - Exfiltration Over C2 Channel

Command and Control - Non-Standard Port

Command and Control – Web Service

Impact - Data Encrypted for Impact

List of IoCs

IoC         Type      Description + Probability

193.242.184[.]178 - IP Address - Possible Exfiltration Server  

45.32.205[.]52  - IP Address  - Possible C2 Infrastructure

45.32.90[.]176 - IP Address - Possible C2 Infrastructure

207.246.74[.]166 - IP Address - Likely C2 Infrastructure

67.217.57[.]252 - IP Address - Likely C2 Infrastructure

23.150.248[.]189 - IP Address - Possible Exfiltration Server

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About the author
Alexandra Sentenac
Cyber Analyst

Blog

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Identity

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July 8, 2025

Top Eight Threats to SaaS Security and How to Combat Them

login screen for mutli factor authentication Default blog imageDefault blog image

The latest on the identity security landscape

Following the mass adoption of remote and hybrid working patterns, more critical data than ever resides in cloud applications – from Salesforce and Google Workspace, to Box, Dropbox, and Microsoft 365.

On average, a single organization uses 130 different Software-as-a-Service (SaaS) applications, and 45% of organizations reported experiencing a cybersecurity incident through a SaaS application in the last year.

As SaaS applications look set to remain an integral part of the digital estate, organizations are being forced to rethink how they protect their users and data in this area.

What is SaaS security?

SaaS security is the protection of cloud applications. It includes securing the apps themselves as well as the user identities that engage with them.

Below are the top eight threats that target SaaS security and user identities.

1.  Account Takeover (ATO)

Attackers gain unauthorized access to a user’s SaaS or cloud account by stealing credentials through phishing, brute-force attacks, or credential stuffing. Once inside, they can exfiltrate data, send malicious emails, or escalate privileges to maintain persistent access.

2. Privilege escalation

Cybercriminals exploit misconfigurations, weak access controls, or vulnerabilities to increase their access privileges within a SaaS or cloud environment. Gaining admin or superuser rights allows attackers to disable security settings, create new accounts, or move laterally across the organization.

3. Lateral movement

Once inside a network or SaaS platform, attackers move between accounts, applications, and cloud workloads to expand their foot- hold. Compromised OAuth tokens, session hijacking, or exploited API connections can enable adversaries to escalate access and exfiltrate sensitive data.

4. Multi-Factor Authentication (MFA) bypass and session hijacking

Threat actors bypass MFA through SIM swapping, push bombing, or exploiting session cookies. By stealing an active authentication session, they can access SaaS environments without needing the original credentials or MFA approval.

5. OAuth token abuse

Attackers exploit OAuth authentication mechanisms by stealing or abusing tokens that grant persistent access to SaaS applications. This allows them to maintain access even if the original user resets their password, making detection and mitigation difficult.

6. Insider threats

Malicious or negligent insiders misuse their legitimate access to SaaS applications or cloud platforms to leak data, alter configurations, or assist external attackers. Over-provisioned accounts and poor access control policies make it easier for insiders to exploit SaaS environments.

7. Application Programming Interface (API)-based attacks

SaaS applications rely on APIs for integration and automation, but attackers exploit insecure endpoints, excessive permissions, and unmonitored API calls to gain unauthorized access. API abuse can lead to data exfiltration, privilege escalation, and service disruption.

8. Business Email Compromise (BEC) via SaaS

Adversaries compromise SaaS-based email platforms (e.g., Microsoft 365 and Google Workspace) to send phishing emails, conduct invoice fraud, or steal sensitive communications. BEC attacks often involve financial fraud or data theft by impersonating executives or suppliers.

BEC heavily uses social engineering techniques, tailoring messages for a specific audience and context. And with the growing use of generative AI by threat actors, BEC is becoming even harder to detect. By adding ingenuity and machine speed, generative AI tools give threat actors the ability to create more personalized, targeted, and convincing attacks at scale.

Protecting against these SaaS threats

Traditionally, security leaders relied on tools that were focused on the attack, reliant on threat intelligence, and confined to a single area of the digital estate.

However, these tools have limitations, and often prove inadequate for contemporary situations, environments, and threats. For example, they may lack advanced threat detection, have limited visibility and scope, and struggle to integrate with other tools and infrastructure, especially cloud platforms.

AI-powered SaaS security stays ahead of the threat landscape

New, more effective approaches involve AI-powered defense solutions that understand the digital business, reveal subtle deviations that indicate cyber-threats, and action autonomous, targeted responses.

[related-resource]

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About the author
Carlos Gray
Senior Product Marketing Manager, Email
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