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July 8, 2021

Minimizing the REvil Impact Delivered via Kaseya Servers

Ransomware group REvil recently infiltrated Managed Service Providers for 1,500+ companies. See how Darktrace's autonomous response protected customer data.
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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08
Jul 2021

As the USA prepared for a holiday weekend ahead of the Fourth of July, the ransomware group REvil were leveraging a vulnerability in Kaseya software to attack Managed Service Providers (MSPs) and their downstream customers. At least 1,500 companies appear to have been affected, even ones with no direct relationship to Kaseya.

At the time of writing, it appears that a zero-day vulnerability was used to gain access to the Kaseya VSA servers, before deploying ransomware on the endpoints managed by those VSA servers. This modus operandi vastly differs from previous ransomware campaigns which have traditionally been human-operated, direct intrusions.

The analysis below offers Darktrace’s insights into the campaign by looking at a real-life example. It highlights how Self-Learning AI detected the ransomware attack, and how Antigena protected customer data on the network from being encrypted.

Dissecting REvil ransomware from the network perspective

Antigena detected the first signs of ransomware on the network as soon as encryption had begun. The graphic below illustrates the start of the ransomware encryption over SMB shares. When the graphic was taken, the attack was happening live and had never been seen before. As it was a novel threat, Darktrace stopped the network encryption without any static signatures or rules.

Figure 1: Darktrace detects encryption from the infected device

The ransomware began to take action at 11:08:32, shown by the ‘SMB Delete Success’ from the infected laptop to an SMB server. While the laptop sometimes reads files on that SMB server, it never deletes these types of files on this particular file share, so Darktrace detected this activity as new and unusual.

Simultaneously, the infected laptop created the ransom note ‘943860t-readme.txt’. Again, the ‘SMB Write Success’ to the SMB server was new activity – and crucially, Darktrace did not look for a static string or a known ransom note. Instead – by previously learning the ‘normal’ behavior of every entity, peer group, and the overall enterprise – it identified that the activity was unusual and new for this organization and device.

By detecting and correlating these subtle anomalies, Darktrace identified this as the earliest stages of ransomware encryption on the network and Antigena took immediate action.

Figure 2: Snapshot of Antigena’s actions

Antigena took two precise steps:

  1. Enforce ‘pattern of life’ for five minutes: This prevented the infected laptop from making any connections that were new or unusual. In this case, it prevented any further new SMB encryption activity.
  2. Quarantine device for 24 hours: Usually, Antigena would not take such drastic action, but it was clear that this activity closely resembled ransomware behavior, so Antigena decided to quarantine the device on the network completely to prevent it from doing any further damage.

For several minutes, the infected laptop kept trying to connect to other internal devices via SMB to continue the encryption activity. It was blocked by Antigena at every stage, limiting the spread of the attack and mitigating any damage posed via the network encryption.

Figure 3: End of the attack

On a technical level, Antigena delivered the blocking mechanisms via integrations with native security controls such as existing firewalls, or by taking action itself to disrupt the connections.

The below graphic shows the ‘pattern of life’ for all network connections for the infected laptop. The three red dots represent Darktrace’s detections and pinpoint the exact moment in time when REvil ransomware was installed on the laptop. The graphic also shows an abrupt stop to all network communication as Antigena quarantined the device.

Figure 4: Network connections from the compromised laptop

Attacks will always get in

During the incident, part of the encryption happened locally on the endpoint device, which Darktrace had no visibility over. Furthermore, the Internet-facing Kaseya VSA server that was initially compromised was not visible to Darktrace in this case.

Nevertheless, Self-Learning AI detected the infection as soon as it reached the network. This shows the importance of being able to defend against active ransomware within the enterprise. Organizations cannot rely solely on a single layer of defense to keep threats out. An attacker will always – eventually – breach your environment. Defense therefore needs to change its approach towards detecting and mitigating damage once an adversary is inside.

Many cyber-attacks succeed in bypassing endpoint controls and begin to spread aggressively in corporate environments. Autonomous Response can provide resilience in such cases, even for novel campaigns and new strains of malware.

Thanks to Self-Learning AI, ransomware from the REvil attack could not perform any encryption over the network, and files available on that network were saved. This included the organization’s critical file servers which did not have Kaseya installed and thus did not receive the initial payload via the malicious update directly. By interrupting the attack as it happened, Antigena prevented thousands of files on network shares from being encrypted.

Further observations

Data exfiltration

In contrast to other REvil intrusions Darktrace has caught in the past, no data exfiltration has been observed. This is interesting as it differs from the general trend this last year where cyber-criminal groups generally focus more on the exfiltration of data to hold their victims to ransom, in response to companies becoming better with backups.

Bitcoin

REvil has demanded a total payment of $70 million in Bitcoin. For a group that tries to maximize their profits, this seems odd for two reasons:

  1. How do they expect a single entity to collect $70 million from potentially thousands of affected organizations? They must be aware of the massive logistical challenges behind this, even if they do expect Kaseya to act as a focal point for collecting the money.
  2. Since DarkSide lost access to most of the Colonial Pipeline ransom, ransomware groups have shifted to demanding payments in Monero rather than Bitcoin. Monero appears to be more difficult to track for law enforcement agencies. The fact REvil are using Bitcoin, a more traceable cryptocurrency, appears counter-productive to their usual goal of maximizing profits.

Ransomware-as-a-Service (RaaS)

Darktrace also noticed that other, more traditional ‘big game hunting’ REvil ransomware operations took place over the same weekend. This is not surprising as REvil is running a RaaS model, so it is likely some affiliate groups continued their regular big game hunting attacks while the Kaseya supply chain attack was underway.

Unpredictable is not undefendable

The weekend of the Fourth of July experienced major supply chain attacks against Kaseya and separately, against California-based distributor Synnex. Threats are coming from every direction – leveraging zero-days, social engineering tactics, and other advanced tools.

The case study above demonstrates how self-learning technology detects such attacks and minimizes the damage. It functions as a crucial part of defense-in-depth when other layers – such as endpoint protection, threat intelligence or known signatures and rules – fail to detect unknown threats.

The attack happened in milliseconds, faster than any human security team could react. Autonomous Response has proven invaluable in outpacing this new generation of machine-speed threats. It keeps thousands of organizations safe around the world, around the clock, stopping an attack every second.

Darktrace model detections

  • Compromise / Ransomware / Suspicious SMB Activity
  • Compromise / Ransomware / Suspicious SMB File Extension
  • Compromise / Ransomware / Ransom or Offensive Words Written to SMB
  • Compromise / Ransomware / Ransom or Offensive Words Read from SMB
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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