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November 29, 2020

Darktrace Cyber Analyst Investigates Sodinokibi Ransomware

Darktrace’s Cyber AI Analyst uncovers the intricate details of a Sodinokibi ransomware attack on a retail organization. Dive into this real-time incident.
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
Max Heinemeyer
Global Field CISO
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29
Nov 2020

Sodinokibi is one of the most lucrative ransomware strains of 2020, with its creators, cyber-criminal gang REvil, recently claiming over $100 million in profits this year alone. The prevalent threat is known to wipe backup files, encrypt files on local shares and exfiltrate data.

Exfiltration before encryption is a technique being increasingly adopted by profit-seeking cyber-criminals, who can threaten to leak the stolen data should a target organization not comply with their demands. Sodinobiki also makes heavy use of code obfuscation and encryption techniques to evade detection by signature-based, anti-virus solutions.

Darktrace’s AI recently detected Sodinokibi targeting a retail organization in the US. Prior to this year, the company operated primarily face-to-face in physical stores, but have conducted the majority of their business in the digital realm since the onset of the pandemic.

Cyber AI Analyst automatically launched a full investigation into this incident in real time, as the attack was unfolding. The technology provided summary reports of the entire incident which the security team could immediately action for incident response. This blog explores its findings.

Sodinokibi timeline

Darktrace automatically investigated on the full scope of the Sodinokibi attack, with Cyber AI Analyst clearly identifying and summarising every stage of the attack lifecycle, which played out over the course of three weeks as below:

Figure 1: A timeline of the attack

Darktrace produced a large number of security-relevant anomalies associated with just three credentials, and displayed these along a common timeline shown below:

Figure 2: A timeline view of anomaly detections separated by users. Note the clusters of model breaches for the compromised credentials leading up to October 14.

While a human analyst might have been able to identify these unusual patterns and investigate what caused the clusters of anomalous activity, this process would have taken precious hours during a crisis. Cyber AI Analyst automatically performed the same analysis using supervised machine learning trained on Darktrace’s world-leading analysts, generating meaningful summaries of each stage of the event in real time, as the incident unfolded.

REvil ransomware attack

The following events occurred during a free trial period, and Darktrace was not being actively monitored. Its Autonomous Response technology, Darktrace Antigena, was installed in passive mode, and in the absence of automatic interference at an early stage, this compromise was allowed to unfold without interruption. However, with Darktrace’s AI learning normal ‘patterns of life’ for every device in the background, identifying anomalies, and launching an automated investigation into the attack, we are able to go back into the Threat Visualizer and see how the incident unfolded.

The attack began when the credentials of a highly privileged member of the retail organization’s IT team were compromised. REvil is known to make use of phishing emails, exploit kits, server vulnerabilities, and compromised MSP networks for initial intrusion.

In this case, the attacker used the IT credential to compromise a domain controller and exfiltrate data directly after initial reconnaissance. Darktrace’s AI detected the attacker logging into the domain controller via SMB, writing suspicious files and then deleting batch scripts and log files in the root directory to clear their tracks.

The domain controller then made connections to several rare external endpoints, and Darktrace witnessed a 28MB upload that was likely exfiltration of initial reconnaissance data. Four days later, the attacker connected to the same endpoint (sadstat[.]com) – likely a stager download for C2, which was then initiated via connections on port 443 later that same day.

A week on from the intial C2 connection, a SQL server was detected engaging in network scanning as the attacker sought to move laterally in search of sensitive and valuable data. Over the course of two weeks, Darktrace witnessed unusual internal RDP connections using administrative credentials, before data was uploaded to multiple cloud storage endpoints as well as an SSH server. PsExec was used to deploy the ransomware, resulting in file encryption.

The evasive nature of modern ransomware

REvil started with an inherent advantage in that they were armed with the credentials of a highly privileged IT admin. Nevertheless, they still made several attempts to evade traditional, signature-based tools, such as ‘Living off the Land’ – using common tools such PsExec, WMI, RDP to blend into to legitimate activity.

They leveraged frequently-used cloud storage solutions like Dropbox and pCloud for data transfer, and they conducted SSH on port 443, blending in with SSL connections on the same port. They used a newly-registered domain for C2 communication, meaning Open Source Intelligence Tools (OSINT) were blind to the threat.

Finally, the malware itself was evasive in that it made use of code obfuscation and encryption, and had no need for a system library or API imports. This is the basis for most modern ransomware attacks, and the reality is signature-based tools cannot keep up. Darktrace’s AI not only detected the anomalous activity associated with every stage of the attack, but generated fleshed-out summaries of each stage of the attack with Cyber AI Analyst.

Cyber AI Analyst: Real-time incident reporting

Between September 21 and October 12, Cyber AI Analyst created 15 incidents, investigating dozens of point detections and creating a coherent attack narrative.

Figure 3: Cyber AI Incident log of the first compromised DC. This incident tab details the connections to sadstat[.]com

Figure 4: The DC establishes C2 to the first GHOSTnet GmbH IP

Figure 5: This incident tab highlights the file encryption of files on network shares

Figure 6: Darktrace surfaces the IT admin account takeover

Figure 7: Example of a client type device involved in extensive administrative RDP and SMB activity, as well as data uploads to Dropbox (this upload to Dropbox occurs few seconds before file encryption begins)

REvil vs AI

This Sodinokibi ransomware attack slipped under the radar of a range of traditional tools deployed by the retail organization. However, despite the threat dwelling in the retail organization’s digital environment for over a month, and REvil using local tools to blend in to regular traffic, from Darktrace’s perspective these actions were noisy in comparison to the organization’s normal ‘pattern of life’, setting off a series of alerts and investigations.

Darktrace’s Cyber AI Analyst was able to autonomously investigate nearly every attack phase of the ransomware. The technology works around the clock, without requiring training or time off, and can often reduce hours or days of incident response into just minutes, reducing time to triage by up to 92% and augmenting the capabilities of the human security team.

Thanks to Darktrace analyst Joel Lee for his insights on the above threat find.

Learn more about Cyber AI Analyst

Darktrace model detections:

  • Anomalous Connection / Active Remote Desktop Tunnel
  • Anomalous Connection / Data Sent To New External Device
  • Anomalous Connection / Data Sent to Rare Domain
  • Anomalous Connection / High Volume of New or Uncommon Service Control
  • Anomalous Connection / SMB Enumeration
  • Anomalous Connection / Uncommon 1 GiB Outbound
  • Anomalous Connection / Unusual Admin RDP Session
  • Anomalous Connection / Unusual Admin SMB Session
  • Anomalous File / Internal / Additional Extension Appended to SMB File
  • Anomalous Server Activity / Anomalous External Activity from Critical Network Device
  • Compliance / SMB Drive Write
  • Compliance / Possible Tor Usage
  • Compromise / Ransomware / Ransom or Offensive Words Written to SMB
  • Compromise / Ransomware / Suspicious SMB Activity
  • Device / ICMP Address Scan
  • Device / Multiple Lateral Movement Model Breaches
  • Device / Network Scan
  • Device / New or Uncommon WMI Activity
  • Device / New or Unusual Remote Command Execution
  • Device / RDP Scan
  • Device / Suspicious Network Scan Activity
  • Unusual Activity / Enhanced Unusual External Data Transfer
  • Unusual Activity / Unusual Internal Connections
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
Max Heinemeyer
Global Field CISO

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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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About the author
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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About the author
David Ison
Cyber Analyst
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