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January 14, 2020

How RESPOND Neutralizes Zero-Day Ransomware Attacks

Discover how Cyber AI is taking back the advantage over cyber security threats. See how Darktrace helps save time, money, resources, and reputation.
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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14
Jan 2020

The FBI estimates that, on average, more than 4,000 ransomware attacks have occurred every day since 2016. Operating at machine speeds, ransomware is capable of wreaking havoc on a digital enterprise within mere seconds. And unfortunately, traditional security tools are only programmed to detect known cyber-threats using rules and signatures – leaving them blind to tailored and novel ransomware threats that have never been seen before in the wild.

Because Darktrace’s fundamental approach to cyber defense does not rely on rules and signatures to identify emerging threats, it is in a unique position to neutralize novel attacks. In one recent customer environment, Darktrace RESPOND (formerly known as 'Antigena') stopped a previously-unknown ‘zero-day’ ransomware attack targeting an electronics manufacturer. Even when deployed over a fraction of the digital estate, Darktrace RESPOND was able to neutralize this never-before-seen ransomware strain before it could do any damage.

Imperfect visibility, perfect response

While Darktrace provides 100% coverage of the entire digital infrastructure, from email and cloud to IoT and networks, business challenges sometimes prevent users from obtaining full visibility into their environment. However, even when working with imperfect data and suboptimal coverage, Cyber AI can still identify ongoing threats as they emerge. In the below attack, Darktrace was not covering the initial stages of the attack lifecycle, including the initial infection and command & control establishment – yet the AI was able to autonomously respond within seconds, before the attack escalated into a crisis.

Anatomy of a ransomware attack

In this example, Darktrace’s AI identified patient zero deviating significantly from its typical pattern of internal behavior. This was illustrated by a spike in the pattern of regular connections made by patient zero and a series of high-confidence alerts firing in quick succession. These included:

  1. Compromise / Ransomware / Suspicious SMB Activity — triggers when a device begins making unusual SMB connections across the organization
  2. Antigena Ransomware Block — triggers Antigena to take an action when the behavior is significantly similar to ransomware
  3. Device / Reverse DNS Sweep — triggers when a device makes unusual reverse DNS lookups, a tactic often used during reconnaissance

Figure 1: Several Darktrace alerts fire, and a deviation from the regular pattern of life is visible

Indeed, not only was the device observed making an unexpectedly large number of connections, but it was also reading and writing a large number of SMB files and transferring this data internally to a server it did not usually communicate with. The spike in internal connections between patient zero and the server was a strong indicator of malware attempting to move laterally through the network.

Figure 2: Four model breaches observed on October 30th and a dotted line representing Antigena’s actions

Further investigation into the SMB activity revealed that hundreds of Dropbox-related files were accessed on SMB shares that the device had not previously accessed. Moreover, several of these files started becoming encrypted, appended with a [HELP_DECRYPT] extension.

Figure 3: Darktrace detects SMB activity relating to Dropbox files

Fortunately, Darktrace RESPOND was in Active Mode, and kicked in a second later, enforcing the usual pattern of life by blocking anomalous connections for five minutes, immediately stopping the encryption. By the time Darktrace’s AI took action, only four of these files were successfully encrypted.

Figure 4: Darktrace RESPOND kicks in 1 second after ransomware was detected

Figure 5: More Antigena (RESPOND) alerts and a clear indication of the unusual activity detected

RESPOND then took a second action to stop the ransomware from spreading to other devices. The combination of various anomalous activities was sufficient evidence for Autonomous Response to neutralize the threat: patient zero was quarantined for 24 hours, unable to connect to the server or any other device on the network.

Figure 6: Darktrace stops the infected device from conducting lateral movement & ransom activity

Darktrace RESPOND therefore not only stopped the encryption activity in its tracks, but also prevented the attackers from moving laterally across the network unimpeded – either by scanning, using harvested admin credentials, or performing internal reconnaissance. Autonomous Response initiated a surgical intervention that halted the malware’s spread, all while allowing normal business operations to continue.

No signatures, no problem

Crucially, this strain of ransomware was not associated with any publicly known indicators of compromise such as blacklisted command & control domains or malware file hashes. Darktrace was able to detect this never-before-seen attack based purely on its comprehensive understanding of the normal pattern of life for every device and user within the organization. Once the deviation from this normal behavior was identified, Antigena was able to stop it immediately – without relying on rules, signatures, or historical data. With autonomous response acting decisively and immediately, the security team had enough time to catch up and perform hands-on incident response work.

Darktrace’s AI provides a potent combination: Darktrace DETECT's capacity to reveal deviations in a device’s behavior together with RESPOND acting to block connections and contain the ransomware from spreading across the enterprise. AI-enabled Autonomous Response neutralized the threat by recognizing the lethal recipe of these unusual internal alerts and taking targeted action against the ransomware. This stealthy strain of ransomware is unlikely to have been noticed, let alone stopped, by a security team reliant on legacy tools.

The Return-On-Security-Investment (ROSI) is often discussed when it comes to cyber security expenditure, and this incident provides a great example of the ROSI manifesting itself – recent ransomware attacks usually demand hundreds of thousands of dollars’ worth of ransom payments. Without Darktrace RESPOND containing the threat at an early stage, it is likely that thousands of files would have been encrypted. By relying on Cyber AI, the company was able to take back the advantage over an ever-evolving adversary, saving time, money, resources, and – perhaps most critically – the company’s reputation.

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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