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July 4, 2024

A Busy Agenda: Darktrace's Detection of Qilin Ransomware as a Service Operator

This blog breaks down how Darktrace detected and analyzed Qilin, a Ransomware-as-a-Service group behind recent high-impact attacks. You’ll see how Qilin affiliates customize attacks with flexible encryption, process termination, and double-extortion techniques, as well as why its cross-platform builds in Rust and Golang make it especially evasive. Darktrace highlights three real-world cases where its AI identified likely Qilin activity across customer environments, offering insights into how behavioral detection can spot novel ransomware before disruption occurs. Readers will gain a clear view of Qilin’s toolkit, tactics, and how self-learning defense adapts to these evolving 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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04
Jul 2024

Qilin ransomware has recently dominated discussions across the cyber security landscape following its deployment in an attack on Synnovis, a UK-based medical laboratory company. The ransomware attack ultimately affected patient services at multiple National Health Service (NHS) hospitals that rely on Synnovis diagnostic and pathology services. Qilin’s origins, however, date back further to October 2022 when the group was observed seemingly posting leaked data from its first known victim on its Dedicated Leak Site (DLS) under the name Agenda[1].

The Darktrace Threat Research team investigated network artifacts related to Qilin and identified three probable cases of the ransomware across the Darktrace customer base between June 2022 and May 2024.

Qilin Ransomware-as-a-Service Operator

Qilin operates as a Ransomware-as-a-Service (RaaS) that employs double extortion tactics, whereby harvested data is exfiltrated and threatened of publication on the group's DLS, which is hosted on Tor. Qilin ransomware has samples written in both the Golang and Rust programming languages, making it compilable with various operating systems, and is highly customizable. When building Qilin ransomware variants to be used on their target(s), affiliates can configure settings such as the encryption mode (i.e., skip-step, percent, and speed), the file extension being appended, files, extensions and directories to be skipped during the encryption, and the processes and services to be terminated, among others[1] [2].  

Trend Micro analysts, who were the first to discover Qilin samples in August 2022, when the name "Agenda" was still used in ransom notes, found that each analyzed sample was customized for the intended victims and that "unique company IDs were used as extensions of encrypted files" [3]. This information is configurable from within the Qilin's affiliate panel's 'Targets' section, shown below. The panel's background image features the eponym Chinese legendary chimerical creature Qilin (pronounced “Ke Lin”). Despite this Chinese mythology reference, Russian language was observed being used by a Qilin operator in an underground forum post aimed at hiring affiliates and advertising their RaaS operation[2].

Figure 1: Qilin ransomware’s affiliate panel.

Qilin's RaaS program purportedly has an attractive affiliates' payment structure, with affiliates allegedly able to earn 80% of ransom payments of USD 3m or less and 85% for payments above that figure[2], making it a possibly appealing option in the RaaS ecosystem.  Publication of stolen data and ransom payment negotiations are purportedly handled by Qilin operators. Qilin affiliates have been known to target companies located around the world and within a variety of industries, including critical sectors such as healthcare and energy.

As Qilin is a RaaS operation, the choice of targets does not necessarily reflect Qilin operators' intentions, but rather that of its affiliates.  Similarly, the tactics, techniques, procedures (TTPs) and indicators of compromise (IoC) identified by Darktrace are associated with the given affiliate deploying Qilin ransomware for their own purpose, rather than TTPs and IoCs of the Qilin group. Likewise, initial vectors of infection may vary from affiliate to affiliate. Previous studies show that initial access to networks were gained via spear phishing emails or by leveraging exposed applications and interfaces.

Differences have been observed in terms of data exfiltration and potential C2 external endpoints, suggesting the below investigations are not all related to the same group or actor(s).

Darktrace’s Threat Research Investigation

June 2022

Darktrace first detected an instance of Qilin ransomware back in June 2022, when an attacker was observed successfully accessing a customer’s Virtual Private Network (VPN) and compromising an administrative account, before using RDP to gain access to the customer’s Microsoft System Center Configuration Manager (SCCM) server

From there, an attack against the customer's VMware ESXi hosts was launched. Fortunately, a reboot of their virtual machines (VM) caught the attention of the security team who further uncovered that custom profiles had been created and remote scripts executed to change root passwords on their VM hosts. Three accounts were found to have been compromised and three systems encrypted by ransomware.  

Unfortunately, Darktrace was not configured to monitor the affected subnets at the time of the attack. Despite this, the customer was able to work directly with Darktrace analysts via the Ask the Expert (ATE) service to add the subnets in question to Darktrace’s visibility, allowing it to monitor for any further unusual behavior.

Once visibility over the compromised SCCM server was established, Darktrace observed a series of unusual network scanning activities and the use of Kali (a Linux distribution designed for digital forensics and penetration testing). Furthermore, the server was observed making connections to multiple rare external hosts, many using the “[.]ru” Top Level Domain (TLD). One of the external destinations the server was attempting to connect was found to be related to SystemBC, a malware that turns infected hosts into SOCKS5 proxy bots and provides command-and-control (C2) functionality.

Additionally, the server was observed making external connections over ports 993 and 143 (typically associated with the use of the Interactive Message Access Protocol (IMAP) to multiple rare external endpoints. This was likely due to the presence of Tofsee malware on the device.

After the compromise had been contained, Darktrace identified several ransom notes following the naming convention “README-RECOVER-<extension/company_id>.txt”” on the network. This naming convention, as well as the similar “<company_id>-RECOVER-README.txt” have been referenced by open-source intelligence (OSINT) providers as associated with Qilin ransom notes[5] [6] [7].

April 2023

The next case of Qilin ransomware observed by Darktrace took place in April 2023 on the network of a customer in the manufacturing sector in APAC. Unfortunately for the customer in this instance, Darktrace RESPOND™ was not active on their environment and no autonomous response actions were taken to contain the compromise.

Over the course of two days, Darktrace identified a wide range of malicious activity ranging from extensive initial scanning and lateral movement attempts to the writing of ransom notes that followed the aforementioned naming convention (i.e., “README-RECOVER-<extension/company_id>.txt”).

Darktrace observed two affected devices attempting to move laterally through the SMB, DCE-RPC and RDP network protocols. Default credentials (e.g., UserName, admin, administrator) were also observed in the large volumes of SMB sessions initiated by these devices. One of the target devices of these SMB connections was a domain controller, which was subsequently seen making suspicious WMI requests to multiple devices over DCE-RPC and enumerating SMB shares by binding to the ‘server service’ (srvsvc) named pipe to a high number of internal devices within a short time frame. The domain controller was further detected establishing an anomalously high number of connections to several internal devices, notably using the RDP administrative protocol via a default admin cookie.  

Repeated connections over the HTTP and SSL protocol to multiple newly observed IPs located in the 184.168.123.0/24 range were observed, indicating C2 connectivity.  WebDAV user agent and a JA3 fingerprint potentially associated with Cobalt Strike were notably observed in these connections. A few hours later, Darktrace detected additional suspicious external connections, this time to IPs associated with the MEGA cloud storage solution. Storage solutions such as MEGA are often abused by attackers to host stolen data post exfiltration. In this case, the endpoints were all rare for the network, suggesting this solution was not commonly used by legitimate users. Around 30 GB of data was exfiltrated over the SSL protocol.

Darktrace did not observe any encryption-related activity on this customer’s network, suggesting that encryption may have taken place locally or within network segments not monitored by Darktrace.

May 2024

The most recent instance of Qilin observed by Darktrace took place in May 2024 and involved a customer in the US. In this case, Darktrace initially detected affected devices using unusual administrative and default credentials, before additional internal systems were observed making extensive suspicious DCE-RPC requests to a range of internal locations, performing network scanning, making unusual internal RDP connections, and transferring suspicious executable files like 'a157496.exe' and '83b87b2.exe'.  SMB writes of the file "LSM_API_service" were also observed, activity which was considered 100% unusual by Darktrace; this is an RPC service that can be abused to enumerate logged-in users and steal their tokens. Various repeated connections likely representative of C2 communications were detected via both HTTP and SSL to rare external endpoints linked in OSINT to Cobalt Strike use. During these connections, HTTP GET requests for the following URIs were observed:

/asdffHTTPS

/asdfgdf

/asdfgHTTP

/download/sihost64.dll

Notably, this included a GET request a DLL file named "sihost64.dll" from a domain controller using PowerShell.  

Over 102 GB of data may have been transferred to another previously unseen endpoint, 194.165.16[.]13, via the unencrypted File Transfer Protocol (FTP). Additionally, many non-FTP connections to the endpoint could be observed, over which more than 783 GB of data was exfiltrated. Regarding file encryption activity, a wide range of destination devices and shares were targeted.

Figure 2: Advanced Search graph displaying the total volume of data transferred over FTP to a malicious IP.

During investigations, Darktrace’s Threat Research team identified an additional customer, also based in the United States, where similar data exfiltration activity was observed in April 2024. Although no indications of ransomware encryption were detected on the network, multiple similarities were observed with the case discussed just prior. Notably, the same exfiltration IP and protocol (194.165.16[.]13 and FTP, respectively) were identified in both cases. Additional HTTP connectivity was further observed to another IP using a self-signed certificate (i.e., CN=ne[.]com,OU=key operations,O=1000,L=,ST=,C=KM) located within the same ASN (i.e., AS48721 Flyservers S.A.). Some of the URIs seen in the GET requests made to this endpoint were the same as identified in that same previous case.

Information regarding another device also making repeated connections to the same IP was described in the second event of the same Cyber AI Analyst incident. Following this C2 connectivity, network scanning was observed from a compromised domain controller, followed by additional reconnaissance and lateral movement over the DCE-RPC and SMB protocols. Darktrace again observed SMB writes of the file "LSM_API_service", as in the previous case, activity which was also considered 100% unusual for the network. These similarities suggest the same actor or affiliate may have been responsible for activity observed, even though no encryption was observed in the latter case.

Figure 3: First event of the Cyber AI Analyst investigation following the compromise activity.

According to researchers at Microsoft, some of the IoCs observed on both affected accounts are associated with Pistachio Tempest, a threat actor reportedly associated with ransomware distribution. The Microsoft threat actor naming convention uses the term "tempest" to reference criminal organizations with motivations of financial gain that are not associated with high confidence to a known non-nation state or commercial entity. While Pistachio Tempest’s TTPs have changed over time, their key elements still involve ransomware, exfiltration, and extortion. Once they've gained access to an environment, Pistachio Tempest typically utilizes additional tools to complement their use of Cobalt Strike; this includes the use of the SystemBC RAT and the SliverC2 framework, respectively. It has also been reported that Pistacho Tempest has experimented with various RaaS offerings, which recently included Qilin ransomware[4].

Conclusion

Qilin is a RaaS group that has gained notoriety recently due to high-profile attacks perpetrated by its affiliates. Despite this, the group likely includes affiliates and actors who were previously associated with other ransomware groups. These individuals bring their own modus operandi and utilize both known and novel TTPs and IoCs that differ from one attack to another.

Darktrace’s anomaly-based technology is inherently threat-agnostic, treating all RaaS variants equally regardless of the attackers’ tools and infrastructure. Deviations from a device’s ‘learned’ pattern of behavior during an attack enable Darktrace to detect and contain potentially disruptive ransomware attacks.

Credit to: Alexandra Sentenac, Emma Foulger, Justin Torres, Min Kim, Signe Zaharka for their contributions.

References

[1] https://www.sentinelone.com/anthology/agenda-qilin/  

[2] https://www.group-ib.com/blog/qilin-ransomware/

[3] https://www.trendmicro.com/en_us/research/22/h/new-golang-ransomware-agenda-customizes-attacks.html

[4] https://www.microsoft.com/en-us/security/security-insider/pistachio-tempest

[5] https://www.trendmicro.com/en_us/research/22/h/new-golang-ransomware-agenda-customizes-attacks.html

[6] https://www.bleepingcomputer.com/forums/t/790240/agenda-qilin-ransomware-id-random-10-char;-recover-readmetxt-support/

[7] https://github.com/threatlabz/ransomware_notes/tree/main/qilin

Darktrace Model Detections

Internal Reconnaissance

Device / Suspicious SMB Scanning Activity

Device / Network Scan

Device / RDP Scan

Device / ICMP Address Scan

Device / Suspicious Network Scan Activity

Anomalous Connection / SMB Enumeration

Device / New or Uncommon WMI Activity

Device / Attack and Recon Tools

Lateral Movement

Device / SMB Session Brute Force (Admin)

Device / Large Number of Model Breaches from Critical Network Device

Device / Multiple Lateral Movement Model Breaches

Anomalous Connection / Unusual Admin RDP Session

Device / SMB Lateral Movement

Compliance / SMB Drive Write

Anomalous Connection / New or Uncommon Service Control

Anomalous Connection / Anomalous DRSGetNCChanges Operation

Anomalous Server Activity / Domain Controller Initiated to Client

User / New Admin Credentials on Client

C2 Communication

Anomalous Server Activity / Outgoing from Server

Anomalous Connection / Multiple Connections to New External TCP Port

Anomalous Connection / Anomalous SSL without SNI to New External

Anomalous Connection / Rare External SSL Self-Signed

Device / Increased External Connectivity

Unusual Activity / Unusual External Activity

Compromise / New or Repeated to Unusual SSL Port

Anomalous Connection / Multiple Failed Connections to Rare Endpoint

Device / Suspicious Domain

Device / Increased External Connectivity

Compromise / Sustained SSL or HTTP Increase

Compromise / Botnet C2 Behaviour

Anomalous Connection / POST to PHP on New External Host

Anomalous Connection / Multiple HTTP POSTs to Rare Hostname

Anomalous File / EXE from Rare External Location

Exfiltration

Unusual Activity / Enhanced Unusual External Data Transfer

Anomalous Connection / Data Sent to Rare Domain

Unusual Activity / Unusual External Data Transfer

Anomalous Connection / Uncommon 1 GiB Outbound

Unusual Activity / Unusual External Data to New Endpoint

Compliance / FTP / Unusual Outbound FTP

File Encryption

Compromise / Ransomware / Suspicious SMB Activity

Anomalous Connection / Sustained MIME Type Conversion

Anomalous File / Internal / Additional Extension Appended to SMB File

Compromise / Ransomware / Possible Ransom Note Write

Compromise / Ransomware / Possible Ransom Note Read

Anomalous Connection / Suspicious Read Write Ratio

IoC List

IoC – Type – Description + Confidence

93.115.25[.]139 IP C2 Server, likely associated with SystemBC

194.165.16[.]13 IP Probable Exfiltration Server

91.238.181[.]230 IP C2 Server, likely associated with Cobalt Strike

ikea0[.]com Hostname C2 Server, likely associated with Cobalt Strike

lebondogicoin[.]com Hostname C2 Server, likely associated with Cobalt Strike

184.168.123[.]220 IP Possible C2 Infrastructure

184.168.123[.]219 IP Possible C2 Infrastructure

184.168.123[.]236 IP Possible C2 Infrastructure

184.168.123[.]241 IP Possible C2 Infrastructure

184.168.123[.]247 IP Possible C2 Infrastructure

184.168.123[.]251 IP Possible C2 Infrastructure

184.168.123[.]252 IP Possible C2 Infrastructure

184.168.123[.]229 IP Possible C2 Infrastructure

184.168.123[.]246 IP Possible C2 Infrastructure

184.168.123[.]230 IP Possible C2 Infrastructure

gfs440n010.userstorage.me ga.co[.]nz Hostname Possible Exfiltration Server. Not inherently malicious; associated with MEGA file storage.

gfs440n010.userstorage.me ga.co[.]nz Hostname Possible Exfiltration Server. Not inherently malicious; associated with MEGA file storage.

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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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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.

[related-resource]

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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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