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February 29, 2024

Protecting Against AlphV BlackCat Ransomware

Learn how Darktrace AI is combating AlphV BlackCat ransomware, including the details of this ransomware and how to protect yourself from it.
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
Sam Lister
Specialist Security Researcher
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29
Feb 2024

As-a-Service malware trending

Throughout the course of 2023, “as-a-Service” strains of malware remained the most consistently observed threat type to affect Darktrace customers, mirroring their overall prominence across the cyber threat landscape. With this trend expected to continue throughout 2024, organizations and their security teams should be prepared to defend their network against increasingly versatile and tailorable malware-as-a-service (MaaS) and ransomware-as-a-service (RaaS) strains [1].

What is ALPHV ransomware?

The ALPHV ransomware, also known as ‘BlackCat’ or ‘Noberus’, is one example of a RaaS strain that has been prominent across the threat landscape over the last few years.

ALPHV is a ransomware strain coded in the Rust programming language. The ransomware is sold as part of the RaaS economy [2], with samples of the ransomware being provided and sold by a criminal group (the RaaS ‘operator’) to other cybercriminals (the RaaS ‘affiliates’) who then gain entry to organizations' networks with the intention of detonating the ransomware and demanding ransom payments.

ALPHV was likely first used in the wild back in November 2021 [3]. Since then, it has become one of the most prolific ransomware strains, with the Federal Bureau of Investigation (FBI) reporting nearly USD 300 million in ALPHV ransom payments as of September 2023 [4].

In December 2023, the FBI and the US Department of Justice announced a successful disruption campaign against the ALPHV group, which included a takedown of the their data leak site, and the release of a decryption tool for the ransomware strain [5], and in February 2024, the US Department of State announced  a reward of up to USD 10 million for information leading to the identification or location of anyone occupying a key leadership position in the group operating the ALPHV ransomware strain [6].

The disruption campaign against the ransomware group appeared to have been successful, as evidenced by the recent, significant decline in ALPHV attacks, however, it would not be surprising for the group to simply return with new branding, in a similar vein to its apparent predecessors, DarkSide and BlackMatter [7].

How does ALPHV ransomware work?

ALPHV affiliates have been known to employ a variety of methods to progress towards their objective of detonating ALPHV ransomware [4]. In the latter half of 2023, ALPHV affiliates were observed using malicious advertising (i.e, malvertising) to deliver a Python-based backdoor-dropper known as 'Nitrogen' to users' devices [8][12]. These malvertising operations consisted in affiliates setting up malicious search engine adverts for tools such as WinSCP and AnyDesk.

Users' interactions with these adverts led them to sites resembling legitimate software distribution sites. Users' attempts to download software from these spoofed sites resulted in the delivery of a backdoor-dropping malware sample dubbed 'Nitrogen' to their devices. Nitrogen has been observed dropping a variety of command-and-control (C2) implants onto users' devices, including Cobalt Strike Beacon and Sliver C2. ALPHV affiliates often used the backdoor access afforded to them by these C2 implants to conduct reconnaissance and move laterally, in preparation for detonating ALPHV ransomware payloads.

Darktrace Detection of ALPHV Ransomware

During October 2023, Darktrace observed several cases of ALPHV affiliates attempting to infiltrate organizations' networks via the use of malvertising to socially engineer users into downloading and installing Nitrogen from impersonation websites such as 'wireshhark[.]com' and wìnscp[.]net (i.e, xn--wnscp-tsa[.]net).

While the attackers managed to bypass traditional security measures and evade detection by using a device from the customer’s IT team to perform its malicious activity, Darktrace DETECT™ swiftly identified the subtle indicators of compromise (IoCs) in the first instance. This swift detection of ALPHV, along with Cyber AI Analyst™ autonomously investigating the wide array of post-compromise activity, provided the customer with full visibility over the attack enabling them to promptly initiate their remediation and recovery efforts.

Unfortunately, in this incident, Darktrace RESPOND™ was not fully deployed within their environment, hindering its ability to autonomously counter emerging threats. Had RESPOND been fully operational here, it would have effectively contained the attack in its early stages, avoiding the eventual detonation of the ALPHV ransomware.

Figure 1: Timeline of the ALPHV ransomware attack.

In mid-October, a member of the IT team at a US-based Darktrace customer attempted to install the network traffic analysis software, Wireshark, onto their desktop. Due to the customer’s configuration, Darktrace's visibility over this device was limited to its internal traffic, despite this it was still able to identify and alert for a string of suspicious activity conducted by the device.

Initially, Darktrace observed the device making type A DNS requests for 'wiki.wireshark[.]org' immediately before making type A DNS requests for the domain names 'www.googleadservices[.]com', 'allpcsoftware[.]com', and 'wireshhark[.]com' (note the two 'h's). This pattern of activity indicates that the device’s user was redirected to the website, wireshhark[.]com, as a result of the user's interaction with a sponsored Google Search result pointing to allpcsoftware[.]com.

At the time of analysis, navigating to wireshhark[.]com directly from the browser search bar led to a YouTube video of Rick Astley's song "Never Gonna Give You Up". This suggests that the website, wireshhark[.]com, had been configured to redirect users to this video unless they had arrived at the website via the relevant sponsored Google Search result [8].

Although it was not possible to confirm this with certainty, it is highly likely that users who visited the website via the appropriate sponsored Google Search result were led to a fake website (wireshhark[.]com) posing as the legitimate website, wireshark[.]com. It seems that the actors who set up this fake version of wireshark[.]com were inspired by the well-known bait-and-switch technique known as 'rickrolling', where users are presented with a desirable lure (typically a hyperlink of some kind) which unexpectedly leads them to a music video of Rick Astley's "Never Gonna Give You Up".

After being redirected to wireshhark[.]com, the user unintentionally installed a malware sample which dropped what appears to be Cobalt Strike onto their device. The presence of Cobalt Strike on the user's desktop was evidenced by the subsequent type A DNS requests which the device made for the domain name 'pse[.]ac'. These DNS requests were responded to with the likely Cobalt Strike C2 server address, 194.169.175[.]132. Given that Darktrace only had visibility over the device’s internal traffic, it did not observe any C2 connections to this Cobalt Strike endpoint. However, the desktop's subsequent behavior suggests that a malicious actor had gained 'hands-on-keyboard' control of the device via an established C2 channel.

Figure 2: Advanced Search data showing an customer device being tricked into visiting the fake website, wireshhark[.]com.

Since the malicious actor had gained control of an IT member's device, they were able to abuse the privileged account credentials to spread Python payloads across the network via SMB and the Windows Management Instrumentation (WMI) service. The actor was also seen distributing the Windows Sys-Internals tool, PsExec, likely in an attempt to facilitate their lateral movement efforts. It was normal for this IT member's desktop to distribute files across the network via SMB, which meant that this malicious SMB activity was not, at first glance, out of place.

Figure 3: Advanced Search data showing that it was normal for the IT member's device to distribute files over SMB.

However, Darktrace DETECT recognized that the significant spike in file writes being performed here was suspicious, even though, on the surface, it seemed ‘normal’ for the device. Furthermore, Darktrace identified that the executable files being distributed were attempting to masquerade as a different file type, potentially in an attempt to evade the detection of traditional security tools.

Figure 4: Event Log data showing several Model Breaches being created in response to the IT member's DEVICE's SMB writes of Python-based executables.

An addition to DETECT’s identification of this unusual activity, Darktrace’s Cyber AI Analyst launched an autonomous investigation into the ongoing compromise and was able to link the SMB writes and the sharing of the executable Python payloads, viewing the connections as one lateral movement incident rather than a string of isolated events. After completing its investigation, Cyber AI Analyst was able to provide a detailed summary of events on one pane of glass, ensuring the customer could identify the affected device and begin their remediation.

Figure 5: Cyber AI Analyst investigation summary highlighting the IT member's desktop’s lateral movement activities.

C2 Activity

The Python payloads distributed by the IT member’s device were likely related to the Nitrogen malware, as evidenced by the payloads’ names and by the network behaviours which they engendered.  

Figure 6: Advanced Search data showing the affected device reaching out to the C2 endpoint, pse[.]ac, and then distributing Python-based executable files to an internal domain controller.

The internal devices to which these Nitrogen payloads were distributed immediately went on to contact C2 infrastructure associated with Cobalt Strike. These C2 connections were made over SSL on ports 443 and 8443.  Darktrace identified the attacker moving laterally to an internal SQL server and an internal domain controller.

Figure 7: Advanced Search data showing an internal SQL server contacting the Cobalt Strike C2 endpoint, 194.180.48[.]169, after receiving Python payloads from the IT member’s device.
Figure 8: Event Log data showing several DETECT model breaches triggering in response to an internal SQL server’s C2 connections to 194.180.48[.]169.

Once more, Cyber AI Analyst launched its own investigation into this activity and was able to successfully identify a series of separate SSL connections, linking them together into one wider C2 incident.

Figure 9: Cyber AI Analyst investigation summary highlighting C2 connections from the SQL server.

Darktrace observed the attacker using their 'hands-on-keyboard' access to these systems to elevate their privileges, conduct network reconnaissance (primarily port scanning), spread Python payloads further across the network, exfiltrate data from the domain controller and transfer a payload from GitHub to the domain controller.

Figure 10: Cyber AI Analyst investigation summary an IP address scan carried out by an internal domain controller.
Figure 12: Event Log data showing an internal domain controller contacting GitHub around the time that it was in communication with the C2 endpoint, 194.180.48[.]169.
Figure 13: Event Log data showing a DETECT model breach being created in response to an internal domain controller's large data upload to the C2 endpoint, 194.180.48[.]169.

After conducting extensive reconnaissance and lateral movement activities, the attacker was observed detonating ransomware with the organization's VMware environment, resulting in the successful encryption of the customer’s VMware vCenter server and VMware virtual machines. In this case, the attacker took around 24 hours to progress from initial access to ransomware detonation.  

If the targeted organization had been signed up for Darktrace's Proactive Threat Notification (PTN) service, they would have been promptly notified of these suspicious activities by the Darktrace Security Operations Center (SOC) in the first instance, allowing them to quickly identify affected devices and quarantine them before the compromise could escalate.

Additionally, given the quantity of high-severe alerts that triggered in response to this attack, Darktrace RESPOND would, under normal circumstances, have inhibited the attacker's activities as soon as they were identified by DETECT. However, due to RESPOND not being configured to act on server devices within the customer’s network, the attacker was able to seamlessly move laterally through the organization's server environment and eventually detonate the ALPHV ransomware.

Nevertheless, Darktrace was able to successfully weave together multiple Cyber AI Analyst incidents which it generated into a thread representing the chain of behavior that made up this attack. The thread of Incident Events created by Cyber AI Analyst provided a substantial account of the attack and the steps involved in it, which significantly facilitated the customer’s post-incident investigation efforts.  

Figure 14: Darktrace's AI Analyst weaved together 33 of the Incident Events it created together into a thread representing the attacker’s chain of behavior.

Conclusion

It is expected for malicious cyber actors to revise and upgrade their methods to evade organizations’ improving security measures. The continued improvement of email security tools, for example, has likely created a need for attackers to develop new means of Initial Access, such as the use of Microsoft Teams-based malware delivery.

This fast-paced ALPHV ransomware attack serves as a further illustration of this trend, with the actor behind the attack using malvertising to convince an unsuspecting user to download the Python-based malware, Nitrogen, from a fake Wireshark site. Unbeknownst to the user, this stealthy malware dropped a C2 implant onto the user’s device, giving the malicious actor the ‘hands-on-keyboard’ access they needed to move laterally, conduct network reconnaissance, and ultimately detonate ALPHV ransomware.

Despite the non-traditional initial access methods used by this ransomware actor, Darktrace DETECT was still able to identify the unusual patterns of network traffic caused by the attacker’s post-compromise activities. The large volume of alerts created by Darktrace DETECT were autonomously investigated by Darktrace’s Cyber AI Analyst, which was able to weave together related activities of different devices into a comprehensive timeline of the attacker’s operation. Given the volume of DETECT alerts created in response to this ALPHV attack, it is expected that Darktrace RESPOND would have autonomously inhibited the attacker’s operation had the capability been appropriately configured.

As the first post-compromise activities Darktrace observed in this ALPHV attack were seemingly performed by a member of the customer’s IT team, it may have looked normal to a human or traditional signature and rules-based security tools. To Darktrace’s Self-Learning AI, however, the observed activities represented subtle deviations from the device’s normal pattern of life. This attack, and Darktrace’s detection of it, is therefore a prime illustration of the value that Self-Learning AI can bring to the task of detecting anomalies within organizations’ digital estates.

Credit to Sam Lister, Senior Cyber Analyst, Emma Foulger, Principal Cyber Analyst

Appendices

Darktrace DETECT Model Breaches

- Compliance / SMB Drive Write

- Compliance / High Priority Compliance Model Breach

- Anomalous File / Internal / Masqueraded Executable SMB Write

- Device / New or Uncommon WMI Activity

- Anomalous Connection / New or Uncommon Service Control

- Anomalous Connection / High Volume of New or Uncommon Service Control

- Device / New or Uncommon SMB Named Pipe

- Device / Multiple Lateral Movement Model Breaches

- Device / Large Number of Model Breaches  

- SMB Writes of Suspicious Files (Cyber AI Analyst)

- Suspicious Remote WMI Activity (Cyber AI Analyst)

- Suspicious DCE-RPC Activity (Cyber AI Analyst)

- Compromise / Connection to Suspicious SSL Server

- Compromise / High Volume of Connections with Beacon Score

- Anomalous Connection / Suspicious Self-Signed SSL

- Anomalous Connection / Anomalous SSL without SNI to New External

- Compromise / Suspicious TLS Beaconing To Rare External

- Compromise / Beacon to Young Endpoint

- Compromise / SSL or HTTP Beacon

- Compromise / Agent Beacon to New Endpoint

- Device / Long Agent Connection to New Endpoint

- Compromise / SSL Beaconing to Rare Destination

- Compromise / Large Number of Suspicious Successful Connections

- Compromise / Slow Beaconing Activity To External Rare

- Anomalous Server Activity / Outgoing from Server

- Device / Multiple C2 Model Breaches

- Possible SSL Command and Control (Cyber AI Analyst)

- Unusual Repeated Connections (Cyber AI Analyst)

- Device / ICMP Address Scan

- Device / RDP Scan

- Device / Network Scan

- Device / Suspicious Network Scan Activity

- Scanning of Multiple Devices (Cyber AI Analyst)

- ICMP Address Scan (Cyber AI Analyst)

- Device / Anomalous Github Download

- Unusual Activity / Unusual External Data Transfer

- Device / Initial Breach Chain Compromise

MITRE ATT&CK Mapping

Resource Development techniques:

- Acquire Infrastructure: Malvertising (T1583.008)

Initial Access techniques:

- Drive-by Compromise (T1189)

Execution techniques:

- User Execution: Malicious File (T1204.002)

- System Services: Service Execution (T1569.002)

- Windows Management Instrumentation (T1047)

Defence Evasion techniques:

- Masquerading: Match Legitimate Name or Location (T1036.005)

Discovery techniques:

- Remote System Discovery (T1018)

- Network Service Discovery (T1046)

Lateral Movement techniques:

- Remote Services: SMB/Windows Admin Shares

- Lateral Tool Transfer (T1570)

Command and Control techniques:

- Application Layer Protocol: Web Protocols (T1071.001)

- Encrypted Channel: Asymmetric Cryptography (T1573.002)

- Non-Standard Port (T1571)

- Ingress Tool Channel (T1105)

Exfiltration techniques:

- Exfiltration Over C2 Channel (T1041)

Impact techniques:

- Data Encrypted for Impact (T1486)

List of Indicators of Compromise

- allpcsoftware[.]com

- wireshhark[.]com

- pse[.]ac • 194.169.175[.]132

- 194.180.48[.]169

- 193.42.33[.]14

- 141.98.6[.]195

References  

[1] https://darktrace.com/threat-report-2023

[2] https://www.microsoft.com/en-us/security/blog/2022/05/09/ransomware-as-a-service-understanding-the-cybercrime-gig-economy-and-how-to-protect-yourself/

[3] https://www.bleepingcomputer.com/news/security/alphv-blackcat-this-years-most-sophisticated-ransomware/

[4] https://www.cisa.gov/news-events/cybersecurity-advisories/aa23-353a

[5] https://www.justice.gov/opa/pr/justice-department-disrupts-prolific-alphvblackcat-ransomware-variant

[6] https://www.state.gov/u-s-department-of-state-announces-reward-offers-for-criminal-associates-of-the-alphv-blackcat-ransomware-variant/

[7] https://www.bleepingcomputer.com/news/security/blackcat-alphv-ransomware-linked-to-blackmatter-darkside-gangs/

[8] https://www.trendmicro.com/en_us/research/23/f/malvertising-used-as-entry-vector-for-blackcat-actors-also-lever.html

[9] https://news.sophos.com/en-us/2023/07/26/into-the-tank-with-nitrogen/

[10] https://www.esentire.com/blog/persistent-connection-established-nitrogen-campaign-leverages-dll-side-loading-technique-for-c2-communication

[11] https://www.esentire.com/blog/nitrogen-campaign-2-0-reloads-with-enhanced-capabilities-leading-to-alphv-blackcat-ransomware

[12] https://www.esentire.com/blog/the-notorious-alphv-blackcat-ransomware-gang-is-attacking-corporations-and-public-entities-using-google-ads-laced-with-malware-warns-esentire

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
Sam Lister
Specialist Security Researcher

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December 18, 2025

Why organizations are moving to label-free, behavioral DLP for outbound email

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Why outbound email DLP needs reinventing

In 2025, the global average cost of a data breach fell slightly — but remains substantial at USD 4.44 million (IBM Cost of a Data Breach Report 2025). The headline figure hides a painful reality: many of these breaches stem not from sophisticated hacks, but from simple human error: mis-sent emails, accidental forwarding, or replying with the wrong attachment. Because outbound email is a common channel for sensitive data leaving an organization, the risk posed by everyday mistakes is enormous.

In 2025, 53% of data breaches involved customer PII, making it the most commonly compromised asset (IBM Cost of a Data Breach Report 2025). This makes “protection at the moment of send” essential. A single unintended disclosure can trigger compliance violations, regulatory scrutiny, and erosion of customer trust –consequences that are disproportionate to the marginal human errors that cause them.

Traditional DLP has long attempted to mitigate these impacts, but it relies heavily on perfect labelling and rigid pattern-matching. In reality, data loss rarely presents itself as a neat, well-structured pattern waiting to be caught – it looks like everyday communication, just slightly out of context.

How data loss actually happens

Most data loss comes from frustratingly familiar scenarios. A mistyped name in auto-complete sends sensitive data to the wrong “Alex.” A user forwards a document to a personal Gmail account “just this once.” Someone shares an attachment with a new or unknown correspondent without realizing how sensitive it is.

Traditional, content-centric DLP rarely catches these moments. Labels are missing or wrong. Regexes break the moment the data shifts formats. And static rules can’t interpret the context that actually matters – the sender-recipient relationship, the communication history, or whether this behavior is typical for the user.

It’s the everyday mistakes that hurt the most. The classic example: the Friday 5:58 p.m. mis-send, when auto-complete selects Martin, a former contractor, instead of Marta in Finance.

What traditional DLP approaches offer (and where gaps remain)

Most email DLP today follows two patterns, each useful but incomplete.

  • Policy- and label-centric DLP works when labels are correct — but content is often unlabeled or mislabeled, and maintaining classification adds friction. Gaps appear exactly where users move fastest
  • Rule and signature-based approaches catch known patterns but miss nuance: human error, new workflows, and “unknown unknowns” that don’t match a rule

The takeaway: Protection must combine content + behavior + explainability at send time, without depending on perfect labels.

Your technology primer: The three pillars that make outbound DLP effective

1) Label-free (vs. data classification)

Protects all content, not just what’s labeled. Label-free analysis removes classification overhead and closes gaps from missing or incorrect tags. By evaluating content and context at send time, it also catches misdelivery and other payload-free errors.

  • No labeling burden; no regex/rule maintenance
  • Works when tags are missing, wrong, or stale
  • Detects misdirected sends even when labels look right

2) Behavioral (vs. rules, signatures, threat intelligence)

Understands user behavior, not just static patterns. Behavioral analysis learns what’s normal for each person, surfacing human error and subtle exfiltration that rules can’t. It also incorporates account signals and inbound intel, extending across email and Teams.

  • Flags risk without predefined rules or IOCs
  • Catches misdelivery, unusual contacts, personal forwards, odd timing/volume
  • Blends identity and inbound context across channels

3) Proprietary DSLM (vs. generic LLM)

Optimized for precise, fast, explainable on-send decisions. A DSLM understands email/DLP semantics, avoids generative risks, and stays auditable and privacy-controlled, delivering intelligence reliably without slowing mail flow.

  • Low-latency, on-send enforcement
  • Non-generative for predictable, explainable outcomes
  • Governed model with strong privacy and auditability

The Darktrace approach to DLP

Darktrace / EMAIL – DLP stops misdelivery and sensitive data loss at send time using hold/notify/justify/release actions. It blends behavioral insight with content understanding across 35+ PII categories, protecting both labeled and unlabeled data. Every action is paired with clear explainability: AI narratives show exactly why an email was flagged, supporting analysts and helping end-users learn. Deployment aligns cleanly with existing SOC workflows through mail-flow connectors and optional Microsoft Purview label ingestion, without forcing duplicate policy-building.

Deployment is simple: Microsoft 365 routes outbound mail to Darktrace for real-time, inline decisions without regex or rule-heavy setup.

A buyer’s checklist for DLP solutions

When choosing your DLP solution, you want to be sure that it can deliver precise, explainable protection at the moment it matters – on send – without operational drag.  

To finish, we’ve compiled a handy list of questions you can ask before choosing an outbound DLP solution:

  • Can it operate label free when tags are missing or wrong? 
  • Does it truly learn per user behavior (no shortcuts)? 
  • Is there a domain specific model behind the content understanding (not a generic LLM)? 
  • Does it explain decisions to both analysts and end users? 
  • Will it integrate with your label program and SOC workflows rather than duplicate them? 

For a deep dive into Darktrace’s DLP solution, check out the full solution brief.

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Carlos Gray
Senior Product Marketing Manager, Email

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December 17, 2025

Beyond MFA: Detecting Adversary-in-the-Middle Attacks and Phishing with Darktrace

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What is an Adversary-in-the-middle (AiTM) attack?

Adversary-in-the-Middle (AiTM) attacks are a sophisticated technique often paired with phishing campaigns to steal user credentials. Unlike traditional phishing, which multi-factor authentication (MFA) increasingly mitigates, AiTM attacks leverage reverse proxy servers to intercept authentication tokens and session cookies. This allows attackers to bypass MFA entirely and hijack active sessions, stealthily maintaining access without repeated logins.

This blog examines a real-world incident detected during a Darktrace customer trial, highlighting how Darktrace / EMAILTM and Darktrace / IDENTITYTM identified the emerging compromise in a customer’s email and software-as-a-service (SaaS) environment, tracked its progression, and could have intervened at critical moments to contain the threat had Darktrace’s Autonomous Response capability been enabled.

What does an AiTM attack look like?

Inbound phishing email

Attacks typically begin with a phishing email, often originating from the compromised account of a known contact like a vendor or business partner. These emails will often contain malicious links or attachments leading to fake login pages designed to spoof legitimate login platforms, like Microsoft 365, designed to harvest user credentials.

Proxy-based credential theft and session hijacking

When a user clicks on a malicious link, they are redirected through an attacker-controlled proxy that impersonates legitimate services.  This proxy forwards login requests to Microsoft, making the login page appear legitimate. After the user successfully completes MFA, the attacker captures credentials and session tokens, enabling full account takeover without the need for reauthentication.

Follow-on attacks

Once inside, attackers will typically establish persistence through the creation of email rules or registering OAuth applications. From there, they often act on their objectives, exfiltrating sensitive data and launching additional business email compromise (BEC) campaigns. These campaigns can include fraudulent payment requests to external contacts or internal phishing designed to compromise more accounts and enable lateral movement across the organization.

Darktrace’s detection of an AiTM attack

At the end of September 2025, Darktrace detected one such example of an AiTM attack on the network of a customer trialling Darktrace / EMAIL and Darktrace / IDENTITY.

In this instance, the first indicator of compromise observed by Darktrace was the creation of a malicious email rule on one of the customer’s Office 365 accounts, suggesting the account had likely already been compromised before Darktrace was deployed for the trial.

Darktrace / IDENTITY observed the account creating a new email rule with a randomly generated name, likely to hide its presence from the legitimate account owner. The rule marked all inbound emails as read and deleted them, while ignoring any existing mail rules on the account. This rule was likely intended to conceal any replies to malicious emails the attacker had sent from the legitimate account owner and to facilitate further phishing attempts.

Darktrace’s detection of the anomalous email rule creation.
Figure 1: Darktrace’s detection of the anomalous email rule creation.

Internal and external phishing

Following the creation of the email rule, Darktrace / EMAIL observed a surge of suspicious activity on the user’s account. The account sent emails with subject lines referencing payment information to over 9,000 different external recipients within just one hour. Darktrace also identified that these emails contained a link to an unusual Google Drive endpoint, embedded in the text “download order and invoice”.

Darkrace’s detection of an unusual surge in outbound emails containing suspicious content, shortly following the creation of a new email rule.
Figure 2: Darkrace’s detection of an unusual surge in outbound emails containing suspicious content, shortly following the creation of a new email rule.
Darktrace / EMAIL’s detection of the compromised account sending over 9,000 external phishing emails, containing an unusual Google Drive link.
Figure 3: Darktrace / EMAIL’s detection of the compromised account sending over 9,000 external phishing emails, containing an unusual Google Drive link.

As Darktrace / EMAIL flagged the message with the ‘Compromise Indicators’ tag (Figure 2), it would have been held automatically if the customer had enabled default Data Loss Prevention (DLP) Action Flows in their email environment, preventing any external phishing attempts.

Figure 4: Darktrace / EMAIL’s preview of the email sent by the offending account.
Figure 4: Darktrace / EMAIL’s preview of the email sent by the offending account.

Darktrace analysis revealed that, after clicking the malicious link in the email, recipients would be redirected to a convincing landing page that closely mimicked the customer’s legitimate branding, including authentic imagery and logos, where prompted to download with a PDF named “invoice”.

Figure 5: Download and login prompts presented to recipients after following the malicious email link, shown here in safe view.

After clicking the “Download” button, users would be prompted to enter their company credentials on a page that was likely a credential-harvesting tool, designed to steal corporate login details and enable further compromise of SaaS and email accounts.

Darktrace’s Response

In this case, Darktrace’s Autonomous Response was not fully enabled across the customer’s email or SaaS environments, allowing the compromise to progress,  as observed by Darktrace here.

Despite this, Darktrace / EMAIL’s successful detection of the malicious Google Drive link in the internal phishing emails prompted it to suggest ‘Lock Link’, as a recommended action for the customer’s security team to manually apply. This action would have automatically placed the malicious link behind a warning or screening page blocking users from visiting it.

Autonomous Response suggesting locking the malicious Google Drive link sent in internal phishing emails.
Figure 6: Autonomous Response suggesting locking the malicious Google Drive link sent in internal phishing emails.

Furthermore, if active in the customer’s SaaS environment, Darktrace would likely have been able to mitigate the threat even earlier, at the point of the first unusual activity: the creation of a new email rule. Mitigative actions would have included forcing the user to log out, terminating any active sessions, and disabling the account.

Conclusion

AiTM attacks represent a significant evolution in credential theft techniques, enabling attackers to bypass MFA and hijack active sessions through reverse proxy infrastructure. In the real-world case we explored, Darktrace’s AI-driven detection identified multiple stages of the attack, from anomalous email rule creation to suspicious internal email activity, demonstrating how Autonomous Response could have contained the threat before escalation.

MFA is a critical security measure, but it is no longer a silver bullet. Attackers are increasingly targeting session tokens rather than passwords, exploiting trusted SaaS environments and internal communications to remain undetected. Behavioral AI provides a vital layer of defense by spotting subtle anomalies that traditional tools often miss

Security teams must move beyond static defenses and embrace adaptive, AI-driven solutions that can detect and respond in real time. Regularly review SaaS configurations, enforce conditional access policies, and deploy technologies that understand “normal” behavior to stop attackers before they succeed.

Credit to David Ison (Cyber Analyst), Bertille Pierron (Solutions Engineer), Ryan Traill (Analyst Content Lead)

Appendices

Models

SaaS / Anomalous New Email Rule

Tactic – Technique – Sub-Technique  

Phishing - T1566

Adversary-in-the-Middle - T1557

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