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March 22, 2022

Stopping Trickbot: Darktrace's Autonomous Response

Darktrace's autonomous response successfully thwarted a Trickbot intrusion. See how AI played a crucial role in this defense.
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
Tony Jarvis
VP, Field CISO
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22
Mar 2022

In the lead-up to the 2020 US election, Microsoft and its partners attempted to bring down the pernicious Trickbot malware and reduce election tampering attempts. These efforts were successful, to an extent: the takedown effectively eliminated 94% of Trickbot’s infrastructure and massively reduced its influence in late 2020.

Malware rarely stays dead, however. We discussed previously how the arrests which followed REvil’s widespread attacks in 2021 have done little to disrupt that group’s Ransomware-as-a-Service operation, and how Ryuk ransomware fell into new hands after being abandoned by its creators.

Trickbot has seen a resurrection of even greater proportions. By June 2021, when Darktrace detected a Trickbot intrusion in one of its customer environments, the malware was far from a forgotten, ineffectual strain. It had instead become the most prevalent malware in the world.

It was only due to a last-minute activation of Darktrace’s Autonomous Response that this customer was able to avoid falling victim to a successful ransomware attack. Because it can take action at any stage of an attack, Autonomous Response could interrupt Trickbot even after it had taken root within the digital environment, and successfully prevent the execution of ransomware.

Trickbot takes root

The intrusion took place at a public administration organization in the EMEA region. Prior to Darktrace’s deployment, a single internal domain controller had been compromised by Trickbot, which then lay dormant for at least a month. By the time the malware began to take action, however, Darktrace’s AI had been deployed. Despite entering a compromised environment, the AI was able to differentiate between benign and malicious activity and immediately detect the threat, though at this point Autonomous Response was configured to not take any action without human confirmation.

Darktrace detected the compromised domain controller uploading a malicious DLL file – very likely Trickbot itself – to approximately 280 devices in the organization over SMB, and then using Windows Management Instrumentation (WMI) to configure and execute it. Despite Trickbot’s age and infamy, tools dependent on threat intelligence remained silent at this stage.

Figure 1: Timeline of the attack

How attackers resurrected Trickbot

Trickbot’s modular nature makes it a perfect gateway for a host of criminal activities, and keeps the malware itself adaptable and therefore hard to defend against. The action coordinated by Microsoft successfully took down the known IP addresses of multiple Trickbot command and control (C2) servers and temporarily prevented Trickbot operators from purchasing or leasing new ones. But it did not take long for the Trickbot infrastructure to be rebuilt, and in May and June of 2021 it was again deemed the most prevalent malware in a Global Threat Index.

Trickbot’s ability to evolve and circumvent existing OSINT was demonstrated in this attack, as Darktrace noticed 160 of the 280 compromised devices it had detected beginning to connect to a host of new C2 endpoints. None of these had OSINT associating them with malicious activity, but Darktrace considered the activity highly unusual in the context of previous behavior, and the security team were notified of this potential high-severity incident via a Proactive Threat Notification (PTN).

The attackers laid low for over a month, before the compromised devices were detected downloading masqueraded executable files and conducting anomalous scanning activity. These files were likely Ryuk ransomware payloads. By spacing out these stages of the attack, the threat actors made it harder for human teams to connect the dots and reveal the full scope of the threat.

Darktrace’s Cyber AI Analyst, which investigates and triages threats across entire digital environments, was able to piece these disparate events into a single attack narrative, however, and deliver a further PTN. Due to the severity of the situation, the customer submitted to Darktrace’s Ask the Expert (ATE) service to receive assistance with their threat response.

Figure 2: Cyber AI Analyst investigates suspicious executable files being spread to multiple internal devices

Autonomous Response shuts down a late-stage attack

Having understood the scale of the threat they now faced, the team activated Autonomous Response to take autonomous action to contain the threat. If Autonomous Response had been in place from the beginning, it would have stopped this attack in its earliest stages, while it was restricted to a single compromised domain controller. Crucially, however, Autonomous Response can take action at any stage of a ransomware attack.

Even at this late stage, it was able to halt the attackers and prevent Ryuk from being executed on the network. The AI blocked a chain of malicious activities including SMB enumeration, networking scanning, and suspicious outbound connections in seconds, disrupting the attack while enforcing normal business operations to ensure that the rest of the company’s work could continue uninterrupted.

With their C2 communications and lateral movement efforts disrupted, the attackers were unable to execute Ryuk, and the attack came to an end just in time. It is likely that this last-minute activation of Autonomous Response avoided widespread data encryption and possibly exfiltration, as well as the numerous costs which follow a successful ransomware attack even if a ransom is paid.

Deploying Autonomous Response before it’s too late

Despite only being activated once the attack had taken root, Darktrace was still able to distinguish malicious activity from normal business operations and stop the threat without causing disruption. Next time an attack strikes, this organization will be prepared with Autonomous Response in fully autonomous mode from the outset, ready to take action at the first sign of an emerging threat and minimize their remediation efforts.

The journey to fully autonomous security requires organizations to build trust in AI’s accuracy and decision-making. What this journey looks like for each individual organization will differ, but the need for technology that can autonomously respond to emerging threats is not a lesson any organization ought to learn the hard way.

Thanks to Darktrace analyst Sam Lister for his insights on the above threat find.

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
Tony Jarvis
VP, 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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