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December 2, 2019

Containing Cyber Threats with Autonomous Response

Autonomous response technology can stop cyber threats in their tracks. Discover how these solutions enable rapid threat containment.
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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02
Dec 2019
“The next phase in our journey toward autonomous security is Autonomous Response decision-making.”

Lawrence Pingree, Research Vice President, Gartner

We’ve talked extensively on this blog about Autonomous Response: the AI-powered technology that, according to Gartner, represents a paradigm shift in cyber defense. As the first such Autonomous Response tool, Darktrace Antigena has already thwarted countless cyber-attacks, from a spear phishing campaign against a major city to an IoT smart locker attack targeting a popular amusement park. Antigena’s surgical intervention afforded their security teams the time they needed to investigate — stopping the clock in seconds by containing just the malicious behavior.

For all its benefits, however, Autonomous Response does have one drawback: it can make for slightly anticlimactic blog posts. In place of captivating, step-by-step descriptions of malware spreading throughout the enterprise and inflicting irrevocable damage, Antigena case studies end a mere moment after they start, with the “patient zero” employee completely unaware of the compromise that could have been.

In this particular case, however, Antigena was deployed in Human Confirmation Mode — a starter mode wherein the AI’s actions must first be approved by the security team. Absent such approval, the result was both an in-depth look at a sophisticated ransomware attack, as well as a remarkable illustration of how Antigena reacted in real time to every stage of that attack’s lifecycle:

Initial download

Patient zero here was a device that Darktrace detected downloading an executable file from a server with which no other devices on the network had ever communicated. Downloads like this one regularly bypass conventional endpoint tools, since they cannot be programmed in advance to catch the full range of unpredictable future threats. By contrast, because Darktrace AI learned the typical behavior of the company’s unique users and devices while ‘on the job’, it easily determined the download to be anomalous.

Figure 1: Darktrace alerts on the 100% rare connection and subsequent download — as it occurs.

Had Antigena been in Active Mode at the time, this would have marked the end of the blog post. By blocking all connections to the associated IP and port, Antigena would have instantly stopped the download — without otherwise impacting the device at all.

Figure 2: Antigena, in Human Confirmation Mode, recommends that it block the suspicious activity.

Command and control

Following the download, Darktrace observed the device making an HTTP GET request to the same rare endpoint. The continuation of this suspicious activity precipitated an escalation in Antigena’s recommended response, which would now have blocked all outgoing traffic from the breached device to prevent any infection from spreading.

Darktrace then detected the device making yet more unusual external connections to endpoints that, in many cases, had self-signed SSL certificates. Such self-signed certificates do not require verification by a trusted authority and are therefore frequently utilized by cyber-criminals. As a consequence, the outgoing connections from our infected device are likely the installed malware communicating with its command and control infrastructure, as Darktrace flagged below:

Figure 3: Darktrace alerts on the suspicious SSL certificates.

Figure 4: Antigena recommends taking action to block the connections in question.

Internal reconnaissance

Beyond the unusual external activity observed from the breached device, it also began to deviate significantly from its typical pattern of internal behavior. Indeed, Darktrace detected the device making over 160,000 failed internal connections on two key ports: Remote Desktop Protocol port 3389 and SMB port 445. This activity — known as network scanning — provides crucial reconnaissance, giving the attacker insight into the network structure, the services available on each device, and any potential vulnerabilities. Ports 3389 and 445 are especially common targets.

Figure 5: Darktrace tracks this ransomware attack at every step, though the security team does not mount a response in time.

The unusual external connections to self-signed SSL certificates, combined with the highly anomalous internal connectivity from the device, would have caused Antigena to escalate further. Alas, the attack proceeds.

Darktrace detected no further anomalous activity from patient zero for the next four days — perhaps a mechanism to remain under the radar. Yet this period of dormancy concluded when, once again, the device connected to a rare domain with a self-signed SSL certificate, likely reaching out to its command and control infrastructure for additional instructions.

Lateral movement

A day later — in a sign that suggests the prior scanning was somewhat fruitful — the infected device performed a large amount of unusual SMB activity consistent with the malware attempting to move laterally across the network. Darktrace picked up on the breached device sending unusual outgoing SMB writes to the remote administration tool PsExec to a total of 38 destination devices, 28 of which it compromised with a malicious file.

Darktrace recognized this activity as highly anomalous for the particular device, as it doesn’t usually communicate with these destination devices in this manner. Antigena would therefore would have surgically blocked the remote administration behavior by first containing the patient zero device to its normal ‘pattern of life’, and then by escalating to blocking all outgoing connections from the device if lateral movement had continued. Antigena’s escalation can be seen below: the first action is taken at 08:03, the second, more severe action at 08:43.

Figure 6: Darktrace repeatedly alerts on the unusual SMB traffic with high confidence — thanks to its evolving understanding of the device’s typical ‘pattern of life’.
Figure 7: Antigena again recommends immediate intervention, this time to impede lateral movement.

Encryption

Darktrace observed the first sign of the ransomware’s ultimate objective — encrypting files — on a different device, which also performed a large volume of unusual SMB activity. After accessing a multitude of SMB shares that it hadn’t accessed previously, it systematically appended those files with the .locked extension. When all was said and done, this encryption activity was seen from no less than 40 internal devices.

In Active Mode, Antigena Ransomware Block would have fully quarantined the devices — a culmination of increasingly severe Antigena actions from the initial infection of patient zero, to the command and control communication, to the internal reconnaissance, to the lateral movement, and finally to the file encryption.

Figure 8: Antigena Ransomware Block was fully armed and prepared to fight back against the infection.

The case for boring blog posts

No other approach to cyber security is able to track ransomware so comprehensively throughout its lifecycle, as programming legacy tools to flag all remote administration behavior, for instance, would inundate security teams with thousands of false positive alerts. Thus, only Darktrace’s understanding ‘self’ for each infected device can shed light on such activities — in the rare cases when they are anomalous.

Figure 9: An overview of Darktrace’s myriad warnings throughout the five-day attack with each colored dot representing a high-confidence alert.

However, intriguing though it may be to track this lifecycle to conclusion, the technology to write far less intriguing blog posts already exists and is already proven. Autonomous Response will render this kind of threat story a relic of the past, and for organizations with sensitive data and critical intellectual property to safeguard, the days of boring security blogs cannot come soon enough.

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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