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November 13, 2022

Prevent Brand Abuse with Darktrace | Protect Your Brand

Prevent brand abuse with Darktrace's AI-powered solution. Detect and stop impersonation attacks before they harm your reputation. Read to learn more here.
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
Elliot Stocker
Product SME
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13
Nov 2022

Brand abuse refers to the unauthorized imitation of an organization's brand. Its discovery is often a reminder to organizations that they need to protect more than just their data and IP – their reputation is at stake. But brand impersonation can also be used to launch a direct attack against the organization – and those around it. 

During a first demonstration meeting recently, Darktrace PREVENT discovered a website deploying a classic trick: the letters ‘rn’ were used in sequence in an attempt to imitate the letter ‘m’ in the company’s name (e.g. “exarnple-brand.com”). Whilst obvious when you’re looking out for it, for an unsuspecting employee this goes easily unnoticed. 

This website was set up by an attacker two weeks before the PREVENT demo. The website was taken down immediately, and the company was also advised to launch an internal investigation to find out if somebody had received an email from this address. The company also launched an information campaign informing their supply chain of this attack, and this last activity resulted in the discovery that one of their suppliers had been scammed through the same email domain and had transferred a large sum of money towards a shell company that was not related to the main brand. By alerting that supplier, additional money transfers were prevented.

This example is part of a broader trend being seen across the industry. ZDNET’s Fraud Trends Report found that roughly 250,000 attacks in Q2 of 2021 involved some form of brand abuse. These attacks harm companies by inflicting reputational damage, incurring financial losses from fraudulent competition, or serving as steppingstones for larger threats like supply chain attacks.

Organizations work hard to cultivate brand identities that differentiate themselves from competitors and build relationships with consumers. Yet, the stronger and more recognizable a brand is, the more often it is targeted for abuse as malicious actors take advantage of their success to reach more victims. Companies with greater online presences or international operations across multiple channels are also at higher risk. 

Brand abuse takes many forms. It can be a website designed to look like it belongs to the brand to collect personal information such as email addresses and passwords. It can be an invoice sent by a vendor with a slight typo in its name. It can be an unauthorized branded webshop that never ships products to buyers. It can be a fake social media account directing customers to malicious websites that distribute malware or spreading fake news. It can be as simple as copyright or trademark infringement.

Figure 1: The general pattern malicious actors use for brand abuse.

Responding to Brand Abuse

Reconquering brand reputation after a brand abuse incident can prove to be much more difficult and costly than investing beforehand to help secure the brand. Risk detection and monitoring require a holistic approach to cover the diverse forms of brand abuse, and requires patrolling the internet for copycats, typo squatters, and other malicious appropriations. 

Figure 2: Mapping to the stages of brand abusein Figure 1, the security team has a set of signals to look for and actions totake to stop brand abuse before it is too late.

Protecting the brand identity and external attack surface can seem like a daunting task for security teams, especially in an age where monitoring internal systems proves enough of a challenge itself. Moreover, how often should the team perform this brand abuse monitoring? Companies can try to search every six months, every quarter, even every month, however there would still be gaps between when a threat actor launches an attack and when the security team discovers it. This is when AI becomes a tremendous ally, as it works at a speed and scale that human teams cannot. 

The Power of PREVENT

PREVENT/Attack Surface ManagementTM works autonomously and continuously to uncover instances of brand abuse, and proactively hardens defenses against any attack that might be launched as a result. 

It uses AI to distinguish a company’s external assets from the rest of the global internet. Its processing features learn brand-related assets such as logos and domain names. It also leverages natural language processing and image classification algorithms to tackle even the most ambiguous and error-prone assets encountered to identify and stop copycats and typosquatters. 

PREVENT/ASM carries out this comprehensive level of monitoring continuously, closing the gap between when an attacker spins up malicious infrastructure and when the security team identifies it. With PREVENT, should an attacker create a malicious website tomorrow morning, the security team will be alerted tomorrow morning. 

In addition to identifying brand abuse, PREVENT/ASM helps the team to collect all the relevant data needed to support a Notice and Takedown procedure. It also integrates with the rest of Darktrace’s security ecosystem to ensure that cyber defense is hardened ahead of time, should malicious assets discovered by PREVENT/ASM be used to launch an attack. 

For example, identifying a webpage impersonating a brand is useful data for email security. PREVENT forewarns Darktrace/Email of malicious domains, which in turn heightens its sensitivity against emails sent from this site. The same is true with regards to network traffic as well as endpoint security: an endpoint device visiting this host will have Darktrace DETECTTM + Darktrace RESPONDTM on higher alert – ready to immediately neutralize threatening activity when it occurs. 

This is the power of the Cyber AI Loop, a virtuous feedback cycle in which AI engines continuously feed into and strengthen one another.

And PREVENT not only identifies instances of brand abuse (along with Shadow IT, misconfigurations, supply chain risk, and other vulnerabilities), but it also prioritizes these risks according to exposure and potential damage and impact. With PREVENT/End-to-EndTM using Darktrace’s understanding of every device and connection inside an organization – every user and their interactions, every possible attack path – insights from the internal and external attack surface combine to give security teams a fully informed understanding of how they can spend their time most effectively to reduce cyber risk. 

In these ways, PREVENT not only monitors for brand abuse at a scope and scale far beyond the capabilities of human security teams, but it also integrates with DETECT + RESPOND to harden a company’s cyber security. 

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
Elliot Stocker
Product SME

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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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