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February 27, 2025

Fighting the Real Enemy: The Importance of Responsible Vulnerability Disclosure Between Email Security Vendors

This blog explores an exploitation capability observed by Darktrace in another email security vendor’s link rewriting and the steps Darktrace took to inform and resolve the issue.
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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.
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27
Feb 2025

Part of being a cybersecurity vendor is recognizing our responsibility to the security community – while vendor competition exists, it pales in comparison to the threat of our shared adversary: malicious threat actors.

Darktrace is proud to be contributing to the shared mission of fighting attackers; without goodwill among defenders that task is made more difficult for everyone. Through collaboration, we can advance security standards across the board and make the world a safer place.  

With that in mind, Darktrace recently observed an exploitation capability latent in a competing email security vendor’s link rewriting infrastructure, which posed a risk to organizations. Following identification, Darktrace was able to report it to the vendor following their disclosure process. We’ll explore the vulnerability, the potential impact it may have had, how it could have been resolved, and the steps Darktrace took to raise it with the vendor.  

Please note that the following vulnerability we’re about to expose has already been resolved, so there is no risk of it being exploited by others. While keeping this vendor anonymous, we also want to thank them for their cordial response and swift remediation of the issue.

For more information about vulnerability disclosure best practices, refer to the UK National Cyber Security Center’s Vulnerability Disclosure Toolkit.

Details of the vulnerability

Let’s take a look at the weakness Darktrace identified in the link rewriting infrastructure.

In January 2025, Darktrace observed that links generated by a URL rewriting infrastructure could be re-engineered by a malicious actor to point to a URL of their choosing. In this way, a threat actor could effectively use the vendor’s domain to create a malicious domain under their control.

Because a majority of security vendors default to trust from known-safe domains, using one of these links as the payload greatly enhances the likelihood of that email being allow-listed to bypass email security, network URL filtering, and other such security tools, to reach the inbox. This issue meant any adversary could have abused the vendor’s safelink structure to deliver a malicious phishing link payload to any organization. It is likely this exploitation capability could have been found and abused at scale if not addressed.

The problem with said vendor’s link rewriting process was in using standard base-64 encoding instead of randomized encoding, so that anyone could replace the value of the parameter “b=” which contains a base64-encoded form of the original link with a base64-encoded form of a URL of their choosing.

This also posed issues from a privacy perspective. If, for example the encoded link was a SharePoint file, all the included folder names would be available for anyone to see in plaintext.

Example of a phishing attack caught by Darktrace that uses another email security solution’s compromised safelink
Fig 1: Example of a phishing attack caught by Darktrace that uses another email security solution’s compromised safelink

How the vulnerability was resolved

The solution for developers is to ensure the use of randomized encoding when developing link rewriting infrastructure to close the possibility of safelinks being deciphered and re-engineered by malicious actors.

Once Darktrace found this link issue we followed the vendor’s disclosure process to report the potential risk to customers and the wider community, while also conducting a review to ensure that Darktrace customers and their supply chains remained safe. We continued to follow up with the company directly to ensure that the vulnerability was fixed.

This instance highlights the importance of vendors having clear and visible vulnerability disclosure processes (such as RFC9116) and being available to listen to the security community in case of disclosures of this nature.

Why Darktrace was obliged to disclose this vulnerability

Here, Darktrace had two responsibilities: to the security community and to our customers.

As a company whose mission is to protect organizations today and for an ever-changing future, we will never stand by if there is a known risk. If attackers had used the safelinks to create new attacks, any organization could have been exposed due to the inherent trust in this vendor’s links within services that distribute or maintain global whitelists, harm which could have been multiplied by the interlinked nature of supply chains.

This means that not only the vendor’s customers were exposed, but any organization with their safelink in a whitelist was also exposed to this vulnerability. For Darktrace customers, an attack using this link would have been detected and stopped across various service offerings, and a secondary escalation by our Cyber AI Analyst would ensure security teams were aware. Even so, Darktrace has a responsibility to these customers to do everything in its power to minimize their exposure to risk, even if it comes from within their own security stack.

Why Darktrace customers remain protected

If a Darktrace / EMAIL, Darktrace / NETWORK, or any other Darktrace ActiveAI Security Platform customer was exposed to this type of vulnerability, our unique Self-Learning AI approach and defense-in-depth philosophy means they stay protected.

Darktrace / EMAIL doesn’t approach links from a binary perspective – as safe, or unsafe – instead every link is analyzed for hundreds of metrics including the content and context in which it was delivered. Because every user’s normal behavior is baselined, Darktrace can immediately detect anomalies in link-sharing patterns that may point to a threat. Furthermore, our advanced link analysis includes metrics on how links perform within a browser and in-depth visual analysis, to detect even well-disguised payloads.

None of Darktrace’s customers were compromised as a result of this vulnerability. But should a customer have clicked on a similar malicious link, that’s where a platform approach to security comes in. Detecting threats that traverse domains is one strength of the Darktrace ActiveAI Security Platform. Our AI correlates data from across the digital estate to spot suspicious activity in the network, endpoint or cloud that may have originated from a malicious email. Darktrace’s Cyber AI Analyst then performs triage and investigation of alerts to raise those of high importance to an incident, allowing for human-analyst validation and escalation.

As demonstrated by finding this vulnerability in another vendor, Darktrace’s R&D teams are always thinking like an attacker as they develop our products, to allow us to remain one step ahead for our customers.

Conclusion

We hope this example can be useful to developers working on link rewriting infrastructure, or to vendors figuring out how to proceed with a disclosure to another vendor. We’re pleased to have been able to collaborate with said vendor in this instance, and hope that it serves to illustrate the importance of defenders working together towards the common goal of keeping organizations safe from hostile cyber actors.

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
The Darktrace Community

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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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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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