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November 13, 2024

Tactics Behind the Royal and Blacksuit Ransomware

Delve into the complexities of the Royal and Blacksuit ransomware strains and their implications for cybersecurity in today’s digital landscape.
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
Signe Zaharka
Principal Cyber Analyst
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13
Nov 2024

What is BlackSuit Ransomware?

Since late 2023, Darktrace has detected BlackSuit ransomware infiltrating multiple customer networks in the US. This ransomware has targeted a wide range of industries, including arts, entertainment, real estate, public administration, defense, and social security.

Emerging in May 2023, BlackSuit is believed to be a spinoff of Royal ransomware due to similarities in code and Conti, and most likely consists of Russian and Eastern European hackers [1]. Recorded Future reported that the ransomware had affected 95 organizations worldwide, though the actual number is likely much higher [2]. While BlackSuit does not appear to focus on any particular sector, it has targeted multiple organizations in the healthcare, education, IT, government, retail and manufacturing industries [3]. Employing double extortion tactics, BlackSuit not only encrypts files but also steals sensitive data to leverage ransom payments.

BlackSuit has demanded over USD 500 million in ransoms, with the highest individual demand reaching USD 60 million [4]. Notable targets include CDK Global, Japanese media conglomerate Kadokawa, multiple educational institutions, Octapharma Plasma, and the government of Brazil [5][6][7][8].

Darktrace’s Coverage of BlackSuit Ransomware Attack

Case 1, November 2023

The earliest attack on a Darktrace customer by BlackSuit was detected at the start of November 2023. The unusual network activity began on a weekend—a time commonly chosen by ransomware groups to increase their chances of success, as many security teams operate with reduced staff. Darktrace identified indicators of the attackers’ presence on the network for almost two weeks, during which a total of 15 devices exhibited suspicious behavior.

The attack commenced with unusual internal SMB (Server Message Block) connections using a compromised service account. An internal device uploaded an executable (zzza.exe) to a domain controller (DC) and shortly after, wrote a script (socks5.ps1) to another device. According to a Cybersecurity Advisory from the CISA (Cybersecurity and Infrastructure Security Agency, US), the script file was a PowerShell reverse proxy [9].

Approximately an hour and a half later, the device to which the script was written exhibited uncommon WMI (Windows Management Instrumentation) activity. Two hours after receiving the executable file, the DC was observed making an outgoing NTLM request, using PowerShell to remotely execute commands, distributing differently named executable files (<PART OF THE CUSTOMER’S NAME>.exe), and controlling services on other devices.

Eighteen hours after the start of the unusual activity, Darktrace detected another device making repeated connections to “mystuff.bublup[.]com”, which the aforementioned CISA Advisory identifies as a domain used by BlackSuit for data exfiltration [9].

About ten minutes after the suspicious executables were distributed across the network, and less than 24 hours after the start of the unusual activity, file encryption began. A total of ten devices were seen appending the “.blacksuit” extension to files saved on other devices using SMB, as well as writing ransom notes (readme.blacksuit.txt). The file encryption lasted less than 20 minutes.

 An example of the contents of a BlackSuit ransom note being written over SMB.
Figure 1: An example of the contents of a BlackSuit ransom note being written over SMB.

During this compromise, external connections to endpoints related to ConnectWise’s ScreenConnect remote management tool were also seen from multiple servers, suggesting that the tool was likely being abused for command-and-control (C2) activity. Darktrace identified anomalous connectivity associated with ScreenConnect was seen up to 11 days after the start of the attack.

10 days after the start of the compromise, an account belonging to a manager was detected adding “.blacksuit” extensions to the customer’s Software-a-Service (SaaS) resources while connecting from 173.251.109[.]106. Six minutes after file encryption began, Darktrace flagged the unusual activity and recommended a block. However, since Autonomous Response mode was not enabled, the customer’s security team needed to manually confirm the action. Consequently, suspicious activity continued for about a week after the initial encryption. This included disabling authentication on the account and an unusual Teams session initiated from the suspicious external endpoint 216.151.180[.]147.

Case 2, February 2024

Another BlackSuit compromise occurred at the start of February 2024, when Darktrace identified approximately 50 devices exhibiting ransomware-related activity in another US customer’s environment. Further investigation revealed that a significant number of additional devices had also been compromised. These devices were outside Darktrace’s purview to the customer’s specific deployment configuration. The threat actors managed to exfiltrate around 4 TB of data.

Initial access to the network was gained via a virtual private network (VPN) compromise in January 2024, when suspicious connections from a Romanian IP address were detected. According to CISA, the BlackSuit group often utilizes the services of initial access brokers (IAB)—actors who specialize in infiltrating networks, such as through VPNs, and then selling that unauthorized access to other threat actors [9]. Other initial access vectors include phishing emails, RDP (Remote Desktop Protocol) compromise, and exploitation of vulnerable public-facing applications.

Similar to the first case, the file encryption began at the end of the working week. During this phase of the attack, affected devices were observed encrypting files on other internal devices using two compromised administrator accounts. The encryption activity lasted for approximately six and a half hours. Multiple alerts were sent to the customer from Darktrace’s Security Operations Centre (SOC) team, who began reviewing the activity within four minutes of the start of the file encryption.

Darktrace’s Cyber AI Analyst clustering together multiple events related to unusual activity on the network, including file encryption over SMB by BlackSuit.
Figure 2: Darktrace’s Cyber AI Analyst clustering together multiple events related to unusual activity on the network, including file encryption over SMB by BlackSuit.
Figure 3: A spike in model alerts on the day when file encryption by BlackSuit was observed in the network.

In this case, the threat actor utilized SystemBC proxy malware for command and control (C2). A domain controller (DC) was seen connecting to 137.220.61[.]94 on the same day the file encryption took place. The DC was also observed connecting to a ProxyScrape domain around the same time, which is related to the SOCKS5 protocol used by SystemBC. During this compromise, RDP, SSH, and SMB were used for lateral movement within the network.

Figure 4: A Cyber AI Analyst investigation alerting to a device on the VPN subnet making suspicious internal SSH connections due to malicious actors moving laterally within the network.

Signs of threat actors potentially being on the network were observed as early as two days prior to the file encryption. This included unusual internal network scanning via multiple protocols (ICMP, SMB, RDP, etc.), credential brute-forcing, SMB access failures, and anonymous SMBv1 sessions. These activities were traced to IP addresses belonging to two desktop devices in the VPN subnet associated with two regular employee user accounts. Threat actors were seemingly able to exploit at least one of these accounts due to LDAP legacy policies being in place on the customer’s environment.

A Cyber AI Analyst incident summary alerting to a device on the VPN subnet conducting internal reconnaissance.
Figure 5: A Cyber AI Analyst incident summary alerting to a device on the VPN subnet conducting internal reconnaissance.
Examples of the proposed Darktrace Autonomous Response actions on the day BlackSuit initiated file encryption.
Figure 6: Examples of the proposed Darktrace Autonomous Response actions on the day BlackSuit initiated file encryption.

Case 3, August 2024

The most recently observed BlackSuit compromise occurred in August 2024, when a device was observed attempting to brute-force the credentials of an IT administrator. This activity continued for 11 days.

Once the admin’s account was successfully compromised, network scanning, unusual WMI, and SAMR (Security Account Manager Remote protocol) activity followed. A spike in the use of this account was detected on a Sunday—once again, the attackers seemingly targeting the weekend—when the account was used by nearly 50 different devices.

The compromised admin’s account was exploited for data gathering via SMB, resulting in the movement of 200 GB of data between internal devices in preparation for exfiltration. The files were then archived using the naming convention “*.part<number>.rar”.

Around the same time, Darktrace observed data transfers from 19 internal devices to “bublup-media-production.s3.amazonaws[.]com,” totaling just over 200 GB—the same volume of data gathered internally. Connections to other Bublup domains were also detected. The internal data download and external data transfer activity took approximately 8-9 hours.

Unfortunately, Darktrace was not configured in Autonomous Response mode at the time of the attack, meaning any mitigative actions to stop the data gathering or exfiltration required human confirmation.  

One of the compromised devices was seen sending 80 GB of data to bublup-media-production.s3.amazonaws[.]com within a span of 4 hours.
Figure 7: One of the compromised devices was seen sending 80 GB of data to bublup-media-production.s3.amazonaws[.]com within a span of 4 hours.

Once the information was stolen, the threat actor moved on to the final stage of the attack—file encryption. Five internal devices, using either the compromised admin account or connecting via anonymous SMBv1 sessions, were seen encrypting files and writing ransom notes to five other devices on the network. The attempts at file encryption continued for around two hours, but Darktrace’s Autonomous Response capability was able to block the activity and prevent the attack from escalating.

Conclusion

The persistent and evolving threat posed by ransomware like BlackSuit underscores the critical importance of robust cybersecurity measures across all sectors. Since its emergence in 2023, BlackSuit has demonstrated a sophisticated approach to infiltrating networks, leveraging double extortion tactics, and demanding substantial ransoms. The cases highlighted above illustrate the varied methods and persistence of BlackSuit attackers, from exploiting VPN vulnerabilities to abusing remote management tools and targeting off-hours to maximize impact.

Although many similar connection patterns, such as the abuse of Bublup services for data exfiltration or the use of SOCKS5 proxies for C2, were observed during cases investigated by Darktrace, BlackSuit actors are highly sophisticated and tailors their attacks to each target organization. The consequences of a successful attack can be highly disruptive, and remediation efforts can be time-consuming and costly. This includes taking the entire network offline while responding to the incident, restoring encrypted files from backups (if available), dealing with damage to the organization’s reputation, and potential lawsuits.

These BlackSuit ransomware incidents emphasize the need for continuous vigilance, timely updates to security protocols, and the adoption of autonomous response technologies to swiftly counteract such attacks. As ransomware tactics continue to evolve, organizations must remain agile and informed to protect their critical assets and data. By learning from these incidents and enhancing their cybersecurity frameworks, organizations can better defend against the relentless threat of ransomware and ensure the resilience of their operations in an increasingly digital world.

Credit to Signe Zaharka (Principal Cyber Analyst) and Adam Potter (Senior Cyber Analyst)

Insights from Darktrace’s First 6: Half-year threat report for 2024

First 6: half year threat report darktrace screenshot

Darktrace’s First 6: Half-Year Threat Report 2024 highlights the latest attack trends and key threats observed by the Darktrace Threat Research team in the first six months of 2024.

  • Focuses on anomaly detection and behavioral analysis to identify threats
  • Maps mitigated cases to known, publicly attributed threats for deeper context
  • Offers guidance on improving security posture to defend against persistent threats

Appendices

Darktrace Model Detections

Anomalous Connection / Data Sent to Rare Domain

Anomalous Connection / High Volume of New or Uncommon Service Control

Anomalous Connection / New or Uncommon Service Control

Anomalous Connection / Rare WinRM Outgoing

Anomalous Connection / SMB Enumeration

Anomalous Connection / Suspicious Activity On High Risk Device

Anomalous Connection / Suspicious Read Write Ratio

Anomalous Connection / Suspicious Read Write Ratio and Unusual SMB

Anomalous Connection / Sustained MIME Type Conversion

Anomalous Connection / Uncommon 1 GiB Outbound

Anomalous Connection / Unusual Admin SMB Session

Anomalous File / Internal / Additional Extension Appended to SMB File

Anomalous File / Internal / Executable Uploaded to DC

Anomalous File / Internal / Unusual SMB Script Write

Anomalous Server Activity / Anomalous External Activity from Critical Network Device

Anomalous Server Activity / Outgoing from Server

Anomalous Server Activity / Rare External from Server

Anomalous Server Activity / Write to Network Accessible WebRoot

Compliance / Outgoing NTLM Request from DC

Compliance / Remote Management Tool On Server

Compliance / SMB Drive Write

Compromise / Beacon to Young Endpoint

Compromise / Beaconing Activity To External Rare

Compromise / Ransomware / Possible Ransom Note Read

Compromise / Ransomware / Possible Ransom Note Write

Compromise / Ransomware / SMB Reads then Writes with Additional Extensions

Compromise / Ransomware / Suspicious SMB Activity

Device / Anomalous RDP Followed By Multiple Model Breaches

Device / EXE Files Distributed to Multiple Devices

Device / Internet Facing Device with High Priority Alert

Device / Large Number of Model Breaches

Device / Large Number of Model Breaches from Critical Network Device

Device / Multiple Lateral Movement Model Breaches

Device / Network Scan

Device / New or Uncommon WMI Activity

Device / New or Unusual Remote Command Execution

Device / New User Agent To Internal Server

Device / SMB Lateral Movement

Device / SMB Session Brute Force (Admin)

Device / Suspicious SMB Scanning Activity

Device / Unusual LDAP Query For Domain Admins

SaaS / Access / Teams Activity from Rare Endpoint

SaaS / Resource / SaaS Resources With Additional Extensions

SaaS / Unusual Activity / Disabled Strong Authentication

SaaS / Unusual Activity / Multiple Unusual SaaS Activity Scores

SaaS / Unusual Activity / Unusual SaaS Activity Score

SaaS / Unusual Activity / Unusual Volume of SaaS Modifications

Unusual Activity / Anomalous SMB Delete Volume

Unusual Activity / Anomalous SMB Move & Write

Unusual Activity / High Volume Client Data Transfer

Unusual Activity / High Volume Server Data Transfer

Unusual Activity / Internal Data Transfer

Unusual Activity / SMB Access Failures

Unusual Activity / Sustained Anomalous SMB Activity

Unusual Activity / Unusual External Data to New Endpoint

User / New Admin Credentials on Client

User / New Admin Credentials on Server

User/ Kerberos Password Bruteforce

Autonomous Response Models

Antigena / Network / External Threat / Antigena File then New Outbound Block

Antigena / Network / External Threat / Antigena Ransomware Block

Antigena / Network / External Threat / Antigena Suspicious Activity Block

Antigena / Network / External Threat / SMB Ratio Antigena Block

Antigena / Network / Insider Threat / Antigena Internal Anomalous File Activity

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

Antigena / Network / Insider Threat / Antigena Large Data Volume Outbound Block

Antigena / Network / Insider Threat / Antigena Network Scan Block

Antigena / Network / Insider Threat / Antigena Unusual Privileged User Activities Block

Antigena / Network / Insider Threat / Antigena Unusual Privileged User Activities Pattern of Life Block

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

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

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

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

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

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

Antigena / Network / Significant Anomaly / Repeated Antigena Breaches

Antigena / SaaS / Antigena Unusual Activity Block

List of Indicators of Compromise (IoCs)

IoC - Type - Description + Confidence

.blacksuit - File extension – When encrypting the files, this extension is appended to the filename – High

readme.blacksuit.txt – ransom note - A file demanding cryptocurrency payment in exchange for decrypting the victim's files and not leaking the stolen data – High

mystuff.bublup[.]com, bublup-media-production.s3.amazonaws[.]com – data exfiltration domains related to an organization and project management app that has document sharing functionality – High

137.220.61[.]94:4001 – SystemBC C2 related IP address (this tool is often used by other ransomware groups as well) - Medium

173.251.109[.]106 – IP address seen during a SaaS BlackSuit compromise (during file encryption) – Medium

216.151.180[.]147 – IP address seen during a SaaS BlackSuit compromise (during an unusual Teams session) - Medium

MITRE ATT&CK Mapping

Tactic - Technqiue

Account Manipulation - PERSISTENCE - T1098

Alarm Suppression - INHIBIT RESPONSE FUNCTION - T0878

Application Layer Protocol - COMMAND AND CONTROL - T1071

Automated Collection - COLLECTION - T1119

Block Command Message - INHIBIT RESPONSE FUNCTION - T0803

Block Reporting Message - INHIBIT RESPONSE FUNCTION - T0804

Browser Extensions - PERSISTENCE - T1176

Brute Force I/O - IMPAIR PROCESS CONTROL - T0806

Brute Force - CREDENTIAL ACCESS - T1110

Client Configurations - RECONNAISSANCE - T1592.004 - T1592

Cloud Accounts - DEFENSE EVASION, PERSISTENCE, PRIVILEGE ESCALATION, INITIAL ACCESS - T1078.004 - T1078

Data Destruction - IMPACT - T1485

Data Destruction - INHIBIT RESPONSE FUNCTION - T0809

Data Encrypted for Impact - IMPACT - T1486

Data from Cloud Storage Object - COLLECTION - T1530

Data Staged - COLLECTION - T1074

Domain Groups - DISCOVERY - T1069.002 - T1069

Email Collection - COLLECTION - T1114

Exfiltration Over C2 Channel - EXFILTRATION - T1041

Exfiltration to Cloud Storage - EXFILTRATION - T1567.002 - T1567

Exploit Public - Facing Application - INITIAL ACCESS - T1190

Exploitation for Privilege Escalation - PRIVILEGE ESCALATION - T0890

Exploitation of Remote Services - LATERAL MOVEMENT - T1210

File and Directory Discovery - DISCOVERY - T1083

File Deletion - DEFENSE EVASION - T1070.004 - T1070

IP Addresses - RECONNAISSANCE - T1590.005 - T1590

Lateral Tool Transfer - LATERAL MOVEMENT - T1570

LLMNR/NBT - NS Poisoning and SMB Relay - CREDENTIAL ACCESS, COLLECTION - T1557.001 - T1557

Modify Alarm Settings - INHIBIT RESPONSE FUNCTION - T0838

Modify Control Logic - IMPAIR PROCESS CONTROL, INHIBIT RESPONSE FUNCTION - T0833

Modify Parameter - IMPAIR PROCESS CONTROL - T0836

Network Service Scanning - DISCOVERY - T1046

Network Share Discovery - DISCOVERY - T1135

Pass the Hash - DEFENSE EVASION, LATERAL MOVEMENT - T1550.002 - T1550

RDP Hijacking - LATERAL MOVEMENT - T1563.002 - T1563

Remote Access Software - COMMAND AND CONTROL - T1219

Remote Desktop Protocol - LATERAL MOVEMENT - T1021.001 - T1021

Remote System Discovery - DISCOVERY - T1018

Rename System Utilities - DEFENSE EVASION - T1036.003 - T1036

Scanning IP Blocks - RECONNAISSANCE - T1595.001 - T1595

Scheduled Transfer - EXFILTRATION - T1029

Service Execution - EXECUTION - T1569.002 - T1569

Service Stop - IMPACT - T1489

SMB/Windows Admin Shares - LATERAL MOVEMENT - T1021.002 - T1021

Stored Data Manipulation - IMPACT - T1565.001 - T1565

Taint Shared Content - LATERAL MOVEMENT - T1080

Valid Accounts - DEFENSE EVASION, PERSISTENCE, PRIVILEGE ESCALATION, INITIAL ACCESS - T1078

Vulnerability Scanning - RECONNAISSANCE - T1595.002 - T1595

Web Protocols - COMMAND AND CONTROL - T1071.001 - T1071

Web Services - RESOURCE DEVELOPMENT - T1583.006 - T1583

Web Shell - PERSISTENCE - T1505.003 - T1505

Windows Management Instrumentation - EXECUTION - T1047

Windows Remote Management - LATERAL MOVEMENT - T1021.006 - T1021

References

1.     https://www.trendmicro.com/en_us/research/23/e/investigating-blacksuit-ransomwares-similarities-to-royal.html

2.     https://www.reuters.com/technology/cybersecurity/blacksuit-hacker-behind-cdk-global-attack-hitting-us-car-dealers-2024-06-27/

3.     https://www.sentinelone.com/anthology/blacksuit/

4.     https://thehackernews.com/2024/08/fbi-and-cisa-warn-of-blacksuit.html

5.     https://www.techtarget.com/whatis/feature/The-CDK-Global-outage-Explaining-how-it-happened

6.     https://therecord.media/japanese-media-kadokawa-investigating-cyber

7.     https://therecord.media/plasma-donation-company-cyberattack-blacksuit

8.     https://thecyberexpress.com/government-of-brazil-cyberattack-by-blacksuit/

9.     https://www.cisa.gov/news-events/cybersecurity-advisories/aa23-061a

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
Signe Zaharka
Principal 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.

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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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