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March 4, 2019

The VR Goldilocks Problem and Value of Continued Recognition

Security and Operations Teams face challenges when it comes to visibility and recognition. Learn more about how we find a solution to the problems!
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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04
Mar 2019

First, some context about VR

Security Operations teams face two fundamental challenges when it comes to 'finding bad'.

The first is gaining and maintaining appropriate visibility into what is happening in our environments. Visibility is provided through data (e.g. telemetry, logs). The trinity of data sources for visibility concern accounts/credentials, devices, and network traffic.

The second challenge is getting good recognition within the scope of what is visible. Recognition is fundamentally about what alerting and workflows you can implement and automate in response to activity that is suspicious or malicious.

Visibility and Recognition each have their own different associated issues.

Visibility is a problem about what is and can be generated and either read as telemetry, or logged and stored locally, or shipped to a central platform. The timelines and completeness of what visibility you have can depend on factors such as how much data you can or can't store locally on devices that generate data - and for how long; what your data pipeline and data platform look like (e.g. if you are trying to centralise data for analysis); or the capability of host software agents you have to process certain information locally.

The constraints on visibility sets the bar for factors like coverage, timelines and completeness of what recognition you can achieve. Without visibility, we cannot recognize at all. With limited visibility, what we can recognize may not have much value. With the right visibility, we can still fail to recognise the right things. And with too much recognition, we can quickly overload our senses.

A good example of a technology that offers the opportunity to solve these challenges at the network layer is Darktrace. Their technology provides visibility, from a network traffic perspective, into data that concerns devices and the accounts/credentials associated with them. They then provide recognition on top of this by using Machine Learning (ML) models for anomaly detection. Their models alert on a wide range of activities that may be indicative of threat activity, (e.g. malware execution and command and control, a technical exploit, data exfiltration and so on).

The major advantage they provide, compared to traditional Intrusion Detection Systems (IDS) and other vendors who also use ML for network anomaly detection, is that you can a) adjust the sensitivity of their algorithms and b) build your own recognition for particular patterns of interest. For example, if you want to monitor what connections are made to one or two servers, you can set up alerts for any change to expected patterns. This means you can create and adjust custom recognition based on your enterprise context and tune it easily in response to how context changes over time.

The Goldilocks VR Matrix

Below is what we call the VR Goldilocks Matrix at PBX Group Security. We use it to assess technology, measure our own capability and processes, and ask ourselves hard questions about where we need to focus to get the most value from our budget, (or make cuts / shift investment) if we need to.

In the squares are some examples of what you (maybe) should think about doing if you find yourself there.

Important questions to ask about VR

One of the things about Visibility and Recognition is that it’s not a given they are ‘always on’. Sometimes there are failure modes for visibility (causing a downstream issue with recognition). And sometimes there are failure modes or conditions under which you WANT to pause recognition.

The key questions you must have answers to about this include:

  • Under what conditions might I lose visibility?
  • How would I know if I have?
  • Is that loss a blind spot (i.e. data is lost for a given time period)…
  • …or is it 'a temporal delay’ (e.g. a connection fails and data is batched for moving from A to B but that doesn’t happen for a few hours)?
  • What are the recognitions that might be impacted by either of the above?
  • What is my expectation for the SLA on those recognitions from ‘cause of alert’ to ‘response workflow’?
  • Under what conditions would I be willing to pause recognition, change the workflow for what happens upon recognition, or stop it all together?
  • What is the stacked ranked list of ‘must, should, could’ for all recognition and why?

Alerts. Alerts everywhere.

More often than not, Security Operations teams suffer the costs of wasted time due to noisy alerts from certain data sources. As a consequence, it's more difficult for them to single out malicious behavior as suspicious or benign. The number of alerts that are generated due to out of the box SIEM platform configurations for sources like Web Proxies and Domain Controllers are often excessive, and the cost to tune those rules can also be unpalatable. Therefore, rather than trying to tune alerts, teams might make a call to switch them off until someone can get around to figuring out a better way. There’s no use having hypothetical recognition, but no workflow to act on what is generate (other than compliance).

This is where technologies that use ML can help. There are two basic approaches...

One is to avoid alerting until multiple conditions are met that indicate a high probability of threat activity. In this scenario, rather than alerting on the 1st, 2nd, 3rd and 4th ‘suspicious activities’, you wait until you have a critical mass of indicators, and then you generate one high fidelity alert that has a much greater weighting to be malicious. This requires both a high level of precision and accuracy in alerting, and naturally some trade off in the time that can pass before an alert for malicious activity is generated.

The other is to alert on ‘suspicious actives 1-4' and let an analyst or automated process decide if this merits further investigation. This approach sacrifices accuracy for precision, but provides rapid context on whether one, or multiple, conditions are met that push the machine(s) up the priority list in the triage queue. To solve for the lower level of accuracy, this approach can make decisions about how long to sustain alerting. For example, if a host triggers multiple anomaly detection models, rather than continue to send alerts (and risk the SOC deciding to turn them off), the technology can pause alerts after a certain threshold. If a machine has not been quarantined or taken off the network after 10 highly suspicious behaviors are flagged, there is a reasonable assumption that the analyst will have dug into these and found the activity is legitimate.

Punchline 1: the value of Continued Recognition even when 'not malicious'

The topic of paused detections was raised after a recent joint exercise between PBX Group Security and Darktrace in testing Darktrace’s recognition. After a machine being used by the PBX Red Team breached multiple high priority models on Darktrace, the technology stopped alerting on further activity. This was because the initial alerts would have been severe enough to trigger a SOC workflow. This approach is designed to solve the problem of alert overload on a machine that is behaving anomalously but is not in fact malicious. Rather than having the SOC turn off alerts for that machine (which could later be used maliciously), the alerts are paused.

One of the outcomes of the test was that the PBX Detect team advised they would still want those alerts to exist for context to see what else the machine does (i.e. to understand its pattern of life). Now, rather than pausing alerts, Darktrace is surfacing this to customers to show where a rule is being paused and create an option to continue seeing alerts for a machine that has breached multiple models.

Which leads us on to our next point…

Punchline 2: the need for Atomic Tests for detection

Both Darktrace and Photobox Security are big believers in Atomic Red Team testing, which involves ‘unit tests’ that repeatedly (or at a certain frequency) test a detection using code. Unit tests automate the work of Red Teams when they discovery control strengths (which you want to monitor continuously for uptime) or control gaps (which you want to monitor for when they are closed). You could design atomic tests to launch a series of particular attacks / threat actor actions from one machine in a chained event. Or you could launch different discreet actions from different machines, each of which has no prior context for doing bad stuff. This allows you to scale the sample size for testing what recognition you have (either through ML or more traditional SIEM alerting). Doing this also means you don't have to ask Red Teams to repeat the same tests again, allowing them to focus on different threat paths to achieve objectives.

Mitre Att&ck is an invaluable framework for this. Many vendors are now aligning to Att&ck to show what they can recognize relating to attack TTPs (Tools, Tactics and Procedures). This enables security teams to map what TTPs are relevant to them (e.g. by using threat intel about the campaigns of threat actor groups that are targeting them). Atomic Red Team tests can then be used to assure that expected detections are operational or find gaps that need closing.

If you miss detections, then you know you need to optimise the recognition you have. If you get too many recognitions outside of the atomic test conditions, you either have to accept a high false positive rate because of the nature of the network, or you can tune your detection sensitivity. The opportunities to do this with technology based on ML and anomaly detection are significant, because you can quickly see for new attack types what a unit test tells you about your current detections and that coverage you think you have is 'as expected'.

Punchline 3: collaboration for the win

Using well-structured Red Team exercises can help your organisation and your technology partners learn new things about how we can collectively find and halt evil. They can also help defenders learn more about good assumptions to build into ML models, as well as covering edge cases where alerts have 'business intelligence' value vs ‘finding bad’.

If you want to understand the categorisations of ways that your populations of machines act over time, there is no better way to do it than through anomaly detection and feeding alerts into a system that supports SOC operations as well as knowledge management (e.g. a graph database).

Working like this means that we also help get the most out of the visibility and recognition we have. Security solutions can be of huge help to Network and Operations teams for troubleshooting or answering questions about network architecture. Often, it’s just a shift in perspective that unlocks cross-functional value from investments in security tech and process. Understanding that recognition doesn’t stop with security is another great example of where technologies that let you build your own logic into recognition can make a huge difference above protecting the bottom line, to adding top line value.

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.

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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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