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May 23, 2023

Darktrace’s Detection of a Hive Ransomware-as-Service

This blog investigates a new strain of ransomware, Hive, a ransomware-as-a-service. Darktrace was able to provide full visibility over the attacks.
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
Emily Megan Lim
Cyber Analyst
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23
May 2023

Update: On January 26, 2023, the Hive ransomware group was dismantled and servers associated with the sale of the ransomware were taken offline following an investigation by the FBI, German law enforcement and the National Crime Agency (NCA). The activity detailed in this blog took place in 2022, whilst the group was still active.

RaaS in Cyber Security

The threat of ransomware continues to be a constant concern for security teams across the cyber threat landscape. With the growing popularity of Ransomware-as-a-Service (RaaS), it is becoming more and more accessible for even inexperienced would-be attackers. As a result of this low barrier to entry, the volume of ransomware attacks is expected to increase significantly.

What’s more, RaaS is a highly tailorable market in which buyers can choose from varied kits and features to use in their ransomware deployments meaning attacks will rarely behave the same. To effectively detect and safeguard against these differentiations, it is crucial to implement security measures that put the emphasis on detecting anomalies and focusing on deviations in expected behavior, rather than relying on depreciated indicators of compromise (IoC) lists or playbooks that focus on attack chains unable to keep pace with the increasing speed of ransomware evolution.

In early 2022, Darktrace DETECT/Network™ identified several instances of Hive ransomware on the networks of multiple customers. Using its anomaly-based detection, Darktrace was able to successfully detect the attacks and multiple stages of the kill chain, including command and control (C2) activity, lateral movement, data exfiltration, and ultimately data encryption and the writing of ransom notes.

Hive Ransomware 

Hive ransomware is a relatively new strain that was first observed in the wild in June 2021. It is known to target a variety of industries including healthcare, energy providers, and retailers, and has reportedly attacked over 1,500 organizations, collecting more than USD 100m in ransom payments [1].

Hive is distributed via a RaaS model where its developers update and maintain the code, in return for a percentage of the eventual ransom payment, while users (or affiliates) are given the tools to carry out attacks using a highly sophisticated and complex malware they would otherwise be unable to use. Hive uses typical tactics, techniques and procedures (TTPs) associated with ransomware, though they do vary depending on the Hive affiliate carrying out the attack.

In most cases a double extortion attack is carried out, whereby data is first exfiltrated and then encrypted before a ransom demand is made. This gives attackers extra leverage as victims are at risk of having their sensitive data leaked to the public on websites such as the ‘HiveLeaks’ TOR website.

Attack Timeline

Owing to the highly customizable nature of RaaS, the tactics and methods employed by Hive actors are expected to differ on a case-by-case basis. Nonetheless in the majority of Hive ransomware incidents identified on Darktrace customer environments, Darktrace DETECT observed the following general attack stages and features. This is possibly indicative of the attacks originating from the same threat actor(s) or from a widely sold batch with a particular configuration to a variety of actors.

Figure 1: A typical timeline of a Hive attack observed by Darktrace.

Initial Access 

Although Hive actors are known to gain initial access to networks through multiple different vectors, the two primary methods reported by security researchers are the exploitation of Microsoft Exchange vulnerabilities, or the distribution of phishing emails with malicious attachments [2][3].

In the early stages of one Hive ransomware attack observed on the network of a Darktrace customer, for example, Darktrace detected a device connecting to the rare external location 23.81.246[.]84, with a PowerShell user agent via HTTP. During this connection, the device attempted to download an executable file named “file.exe”. It is possible that the file was initially accessed and delivered via a phishing email; however, as Darktrace/Email was not enabled at the time of the attack, this was outside of Darktrace’s purview. Fortunately, the connection failed the proxy authentication was thus blocked as seen in the packet capture (PCAP) in Figure 2. 

Shortly after this attempted download, the same device started to receive a high volume of incoming SSL connections from a rare external endpoint, namely 146.70.87[.]132. Darktrace logged that this endpoint was using an SSL certificate signed by Go Daddy CA, an easily obtainable and accessible SSL certificate, and that the increase in incoming SSL connections from this endpoint was unusual behavior for this device. 

It is likely that this highly anomalous activity detected by Darktrace indicates when the ransomware attack began, likely initial payload download.  

Darktrace DETECT models:

  • Anomalous Connection / Powershell to Rare External
  • Anomalous Server Activity / New Internet Facing System
Figure 2: PCAP of the HTTP connection to the rare endpoint 23.81.246[.]84 showing the failed proxy authentication.

C2 Beaconing 

Following the successful initial access, Hive actors begin to establish their C2 infrastructure on infected networks through numerous connections to C2 servers, and the download of additional stagers. 

On customer networks infected by Hive ransomware, Darktrace identified devices initiating a high volume of connections to multiple rare endpoints. This very likely represented C2 beaconing to the attacker’s infrastructure. In one particular example, further open-source intelligence (OSINT) investigation revealed that these endpoints were associated with Cobalt Strike.

Darktrace DETECT models:

  • Anomalous Connection / Multiple Connections to New External TCP
  • Anomalous Server Activity / Anomalous External Activity from Critical Network Device
  • Compromise / High Volume of Connections with Beacon Score
  • Compromise / Sustained SSL or HTTP Increase
  • Compromise / Suspicious HTTP Beacons to Dotted Quad 
  • Compromise / SSL or HTTP Beacon
  • Device / Lateral Movement and C2 Activity

Internal Reconnaissance, Lateral Movement and Privilege Escalation

After C2 infrastructure has been established, Hive actors typically begin to uninstall antivirus products in an attempt to remain undetected on the network [3]. They also perform internal reconnaissance to look for vulnerabilities and open channels and attempt to move laterally throughout the network.

Amid the C2 connections, Darktrace was able to detect network scanning activity associated with the attack when a device on one customer network was observed initiating an unusually high volume of connections to other internal devices. A critical network device was also seen writing an executable file “mimikatz.exe” via SMB which appears to be the Mimikatz attack tool commonly used for credential harvesting. 

There were also several detections of lateral movement attempts via RDP and DCE-RPC where the attackers successfully authenticated using an “Administrator” credential. In one instance, a device was also observed performing ITaskScheduler activity. This service is used to remotely control tasks running on machines and is commonly observed as part of malicious lateral movement activity. Darktrace DETECT understood that the above activity represented a deviation from the devices’ normal pattern of behavior and the following models were breached:

Darktrace DETECT models:

  • Anomalous Connection / Anomalous DRSGetNCChanges Operation
  • Anomalous Connection / New or Uncommon Service Control
  • Anomalous Connection / Unusual Admin RDP Session
  • Anomalous Connection / Unusual SMB Version 1 Connectivity
  • Compliance / SMB Drive Write
  • Device / Anomalous ITaskScheduler Activity
  • Device / Attack and Recon Tools
  • Device / Attack and Recon Tools In SMB
  • Device / EXE Files Distributed to Multiple Devices
  • Device / Suspicious Network Scan Activity
  • Device / Increase in New RPC Services
  • User / New Admin Credentials on Server

Data Exfiltration

At this stage of the attack, Hive actors have been known to carry out data exfiltration activity on infected networks using a variety of different methods. The Cybersecurity & Infrastructure Security Agency (CISA) reported that “Hive actors exfiltrate data likely using a combination of Rclone and the cloud storage service Mega[.]nz” [4]. Darktrace DETECT identified an example of this when a device on one customer network was observed making HTTP connections to endpoints related to Mega, including “w.apa.mega.co[.]nz”, with the user agent “rclone/v1.57.0” with at least 3 GiB of data being transferred externally (Figure 3). The same device was also observed transferring at least 3.6 GiB of data via SSL to the rare external IP, 158.51.85[.]157.

Figure 3: A summary of a device’s external connections to multiple endpoints and the respective amounts of data exfiltrated to Mega storage endpoints.

In another case, a device was observed uploading over 16 GiB of data to a rare external endpoint 93.115.27[.]71 over SSH. The endpoint in question was seen in earlier beaconing activity suggesting that this was likely an exfiltration event. 

However, Hive ransomware, like any other RaaS kit, can differ greatly in its techniques and features, and it is important to note that data exfiltration may not always be present in a Hive ransomware attack. In one incident detected by Darktrace, there were no signs of any data leaving the customer environment, indicating data exfiltration was not part of the Hive actor’s objectives.

Darktrace DETECT models:

  • Anomalous Connection / Data Sent to Rare Domain
  • Anomalous Connection / Lots of New Connections
  • Anomalous Connection / Multiple HTTP POSTs to Rare Hostname
  • Anomalous Connection / Suspicious Self-Signed SSL
  • Anomalous Connection / Uncommon 1 GiB Outbound
  • Device / New User Agent and New IP
  • Unusual Activity / Unusual External Data to New Endpoints
  • Unusual Activity / Unusual External Data Transfer
  • Unusual Activity / Enhanced Unusual External Data Transfer

Ransomware Deployment

In the final stage of a typical Hive ransomware attack, the ransomware payload is deployed and begins to encrypt files on infected devices. On one customer network, Darktrace detected several devices connecting to domain controllers (DC) to read a file named “xxx.exe”. Several sources have linked this file name with the Hive ransomware payload [5].

In another example, Darktrace DETECT observed multiple devices downloading the executable files “nua64.exe” and “nua64.dll” from a rare external location, 194.156.90[.]25. OSINT investigation revealed that the files are associated with Hive ransomware.

Figure 4: Security vendor analysis of the malicious file hash [6] associated with Hive ransomware. 

Shortly after the download of this executable, multiple devices were observed performing an unusual amount of file encryption, appending randomly generated strings of characters to file extensions. 

Although it has been reported that earlier versions of Hive ransomware encrypted files with a “.hive” extension [7], Darktrace observed across multiple customers that encrypted files had extensions that were partially-randomized, but consistently 20 characters long, matching the regular expression “[a-zA-Z0-9\-\_]{8}[\-\_]{1}[A-Za-z0-9\-\_]{11}”.

Figure 5: Device Event Log showing SMB reads and writes of encrypted files with a randomly generated extension of 20 characters. 

Following the successful encryption of files, Hive proceeds to drop a ransom note, named “HOW_TO_DECRYPT.txt”, into each affected directory. Typically, the ransom note will contain a link to Hive’s “sales department” and, in the event that exfiltration took place, a link to the “HiveLeaks” site, where attackers threaten to publish exfiltrated data if their demands are not met (Figure 6).  In cases of Hive ransomware detected by Darktrace, multiple devices were observed attempting to contact “HiveLeaks” TOR domains, suggesting that endpoint users had followed links provided to them in ransom notes.

Figure 6: Sample of a Hive ransom note [4].

Examples of file extensions:

  • 36C-AT9-_wm82GvBoCPC
  • 36C-AT9--y6Z1G-RFHDT
  • 36C-AT9-_x2x7FctFJ_q
  • 36C-AT9-_zK16HRC3QiL
  • 8KAIgoDP-wkQ5gnYGhrd
  • kPemi_iF_11GRoa9vb29
  • kPemi_iF_0RERIS1m7x8
  • kPemi_iF_7u7e5zp6enp
  • kPemi_iF_y4u7pB3d3f3
  • U-9Xb0-k__T0U9NJPz-_
  • U-9Xb0-k_6SkA8Njo5pa
  • zm4RoSR1_5HMd_r4a5a9 

Darktrace DETECT models:

  • Anomalous Connection / SMB Enumeration
  • Anomalous Connection / Sustained MIME Type Conversion
  • Anomalous Connection / Unusual Admin SMB Session
  • Anomalous File / Internal / Additional Extension Appended to SMB File
  • Compliance / SMB Drive Write
  • Compromise / Ransomware / Suspicious SMB Activity
  • Compromise / Ransomware / Ransom or Offensive Words Written to SMB
  • Compromise / Ransomware / Possible Ransom Note Write
  • Compromise / High Priority Tor2Web
  • Compromise / Tor2Web
  • Device / EXE Files Distributed to Multiple Devices

Conclusion

As Hive ransomware attacks are carried out by different affiliates using varying deployment kits, the tactics employed tend to vary and new IoCs are regularly identified. Furthermore, in 2022 a new variant of Hive was written using the Rust programming language. This represented a major upgrade to Hive, improving its defense evasion techniques and making it even harder to detect [8]. 

Hive is just one of many RaaS offerings currently on the market, and this market is only expected to grow in usage and diversity of presentations.  As ransomware becomes more accessible and easier to deploy it is essential for organizations to adopt efficient security measures to identify ransomware at the earliest possible stage. 

Darktrace DETECT’s Self-Learning AI understands customer networks and learns the expected patterns of behavior across an organization’s digital estate. Using its anomaly-based detection Darktrace is able to identify emerging threats through the detection of unusual or unexpected behavior, without relying on rules and signatures, or known IoCs. 

Credit to: Emily Megan Lim, Cyber Analyst, Hyeongyung Yeom, Senior Cyber Analyst & Analyst Team Lead.

Appendices

MITRE AT&CK Mapping

Reconnaissance

T1595.001 – Scanning IP Blocks

T1595.002 – Vulnerability Scanning

Resource Development

T1583.006 – Web Services

Initial Access

T1078 – Valid Accounts

T1190 – Exploit Public-Facing Application

T1200 – Hardware Additions

Execution

T1053.005 – Scheduled Task

T1059.001 – PowerShell

Persistence/Privilege Escalation

T1053.005 – Scheduled Task

T1078 – Valid Accounts

Defense Evasion

T1078 – Valid Accounts

T1207 – Rogue Domain Controller

T1550.002 – Pass the Hash

Discovery

T1018 – Remote System Discovery

T1046 – Network Service Discovery

T1083 – File and Directory Discovery

T1135 – Network Share Discovery

Lateral Movement

T1021.001 – Remote Desktop Protocol

T1021.002 – SMB/Windows Admin Shares

T1021.003 – Distributed Component Object Model

T1080 – Taint Shared Content

T1210 – Exploitation of Remote Services

T1550.002 – Pass the Hash

T1570 – Lateral Tool Transfer

Collection

T1185 – Man in the Browser

Command and Control

T1001 – Data Obfuscation

T1071 – Application Layer Protocol

T1071.001 – Web Protocols

T1090.003 – Multi-hop proxy

T1095 – Non-Application Layer Protocol

T1102.003 – One-Way Communication

T1571 – Non-Standard Port

Exfiltration

T1041 – Exfiltration Over C2 Channel

T1567.002 – Exfiltration to Cloud Storage

Impact

T1486 – Data Encrypted for Impact

T1489 – Service Stop

List of IoCs 

23.81.246[.]84 - IP Address - Likely Malicious File Download Endpoint

146.70.87[.]132 - IP Address - Possible Ransomware Endpoint

5.199.162[.]220 - IP Address - C2 Endpoint

23.227.178[.]65 - IP Address - C2 Endpoint

46.166.161[.]68 - IP Address - C2 Endpoint

46.166.161[.]93 - IP Address - C2 Endpoint

93.115.25[.]139 - IP Address - C2 Endpoint

185.150.1117[.]189 - IP Address - C2 Endpoint

192.53.123[.]202 - IP Address - C2 Endpoint

209.133.223[.]164 - IP Address - Likely C2 Endpoint

cltrixworkspace1[.]com - Domain - C2 Endpoint

vpnupdaters[.]com - Domain - C2 Endpoint

93.115.27[.]71 - IP Address - Possible Exfiltration Endpoint

158.51.85[.]157 - IP Address - Possible Exfiltration Endpoint

w.api.mega.co[.]nz - Domain - Possible Exfiltration Endpoint

*.userstorage.mega.co[.]nz - Domain - Possible Exfiltration Endpoint

741cc67d2e75b6048e96db9d9e2e78bb9a327e87 - SHA1 Hash - Hive Ransomware File

2f9da37641b204ef2645661df9f075005e2295a5 - SHA1 Hash - Likely Hive Ransomware File

hiveleakdbtnp76ulyhi52eag6c6tyc3xw7ez7iqy6wc34gd2nekazyd[.]onion - TOR Domain - Likely Hive Endpoint

References

[1] https://www.justice.gov/opa/pr/us-department-justice-disrupts-hive-ransomware-variant

[2] https://www.varonis.com/blog/hive-ransomware-analysis

[3] https://www.trendmicro.com/vinfo/us/security/news/ransomware-spotlight/ransomware-spotlight-hive 

[4]https://www.cisa.gov/news-events/cybersecurity-advisories/aa22-321a

[5] https://www.trendmicro.com/en_us/research/22/c/nokoyawa-ransomware-possibly-related-to-hive-.html

[6] https://www.virustotal.com/gui/file/60f6a63e366e6729e97949622abd9de6d7988bba66f85a4ac8a52f99d3cb4764/detection

[7] https://heimdalsecurity.com/blog/what-is-hive-ransomware/

[8] https://www.microsoft.com/en-us/security/blog/2022/07/05/hive-ransomware-gets-upgrades-in-rust/ 

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
Emily Megan Lim
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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