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August 11, 2021

How One Email Compromised an Entire Logistics Company

A single phishing email led to a massive compromise at a logistics company in Europe. Discover the importance of email security with increasing SaaS usage.
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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.
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11
Aug 2021

Organizations are only as secure as their weakest link. In many cases, that weak link arises in the various cloud applications an organization relies on. Several high-profile groups including APT28 are known to exploit commonly-used passwords to bruteforce their way into businesses around the world. These ‘spray’ campaigns often target Microsoft Office 365 accounts and will only become more frequent as the use of SaaS increases.

This blog analyses how a single phishing email slipped under the radar of the gateway and other traditional tools in place, and eventually led to mass compromise at a logistics company in Europe.

Logistical nightmare

Logistics operators play a critical role across every industry sector. Managing the distribution of goods and services from the seller to the customer, they enable – or bottleneck – an efficient supply chain. Inevitably, logistics companies have become an attractive target for cyber-criminals, due to the high number of organizations they interact with, the pressure they’re under to deliver on time, and the sensitive data they often handle.

It is a simple equation for attackers: do they put in the hard work to infiltrate 20 well-defended organizations, or compromise just one, and from there gain access to all 20 or more? The majority of cyber-threats Darktrace has observed this year have gone for the latter – exploiting less protected third parties to gain a foothold across a range of businesses.

The vaccine supply in particular has fallen under attack, numerous times. Last autumn, threat actors infiltrated a German biomedical organization and launched a phishing campaign to harvest credentials and compromise several organizations involved in the COVID-19 cold chain.

Alongside ransomware, phishing attacks are one of the most pressing concerns facing the industry.

Breaking the chain

At a medium-sized logistics company, a user received one phishing email from a hijacked third party. The email came from a trusted source with a well established history of sending emails, so it easily passed the gateway.

Once the phishing email had reached the inbox, the user clicked on the malicious link and was led to a fake login page, where they were tricked into divulging their credentials.

Four days later, the attacker logged into the account from an unusual location, and proceeded to read files with sensitive information.

The next day, Darktrace detected a new email rule from another unusual location. Almost immediately, a large volume of outbound emails was sent from the account, all containing the suspicious link.

Figure 1: Timeline of the attack — the total dwell time was five days.

Supply and disrupt

Once you are inside an organization’s digital ecosystem, it is easy to move around and compromise more accounts. Most security tools and employees do not question an internal email sent by a trusted user, especially if the user is a senior figure with authority.

So, after this set of outbound emails, unusual activity from anomalous locations was duly seen on other company accounts. These users had been tricked into giving away their details from the emails supposedly sent by their colleague.

More sensitive customer files were read, followed by a second spike in outbound emails from these hijacked accounts.

This time, the emails were sent not internally, but to external contacts. The contacts likely were conducting business with the logistics company at the time, and so were used to receiving emails from the accounts.

In total, over 450 phishing emails were sent to a wide range of third parties. Many of these third parties in turn had their credentials compromised – repeating the cycle once again.

Figure 2: Cyber AI Analyst investigates the suspicious activity of a compromised user, providing a detailed summary with the unusual login location and actions carried out.

Hanging by a thread: The threat of third-party attacks

The source of the initial phishing email that kickstarted this attack was itself from a legitimate third party known to the customer, where presumably the same thing had occured.

This form of Vendor Email Compromise, which can be rinsed and repeated to form a vicious loop, is notoriously difficult for email security solutions to detect, and can lead to heavy reputational and financial damage. To complicate matters, acting against a suspicious email from a known sender can also cause severe business disruption if it turns out to be legitimate.

Because of this, security must move beyond the binary approach of ‘good’ and ‘bad’, towards a more holistic understanding of the contextual setting surrounding any email interaction.

Darktrace accurately detected the multiple anomalies when comparing it to other emails from senders of the same domain. It sent high-priority alerts to the security team, but could not prevent the email from reaching the inbox because it was only in detection mode.

Figure 3: Darktrace’s automatic summary of the initial phishing email gives an overview of the suspicious aspects of the email.

The phishing links during the attack used a third-party tool called Piktochart, designed to create various type of files such as infographics, charts, and forms. While Piktochart has several legitimate applications, it can also be exploited. Gateways thus have a hard time distinguishing between legitimate and malicious Piktochart links. In this case, the gateway rewrote the initial link for analysis, but did not identify it as malicious.

In comparison, Darktrace for Email easily identified the email to be suspicious because it noticed it was out of character for that particular sender, and because the link itself was suspicious. In active mode, the AI would have locked the link and moved the email to the Junk folder, effectively preventing the very first step of the attack and avoiding any further compromise.

Figure 4: Piktochart was rarely seen on the deployment up until this point – the domain was 100% rare. Darktrace therefore easily detected the anomalous nature of this third-party tool usage.

The butterfly effect

Most cyber-attacks begin with just a single point of entry – that is all an attacker requires. One phishing email can be enough to bring a whole supply chain to its knees. With 94% of cyber-attacks beginning in the inbox, and suppliers and vendors in constant communication over multiple SaaS platforms – including Microsoft Teams and Google Cloud – email security tools must be capable of detecting when a trusted third party is acting abnormally.

Especially with the rise of remote working, SaaS usage has surged in businesses worldwide and many have been forced to turn to cloud and SaaS to enable a flexible workforce. While there are obvious benefits, these additions have expanded the attack surface and stretched the limits of traditional security and human security teams.

When it comes to logistics companies – who often act as the middle man in global operations – credential harvesting not only has serious consequences for the customer, but for anyone in the customer’s email contacts, and can lead to major breaches for numerous people and businesses.

Figure 5: Darktrace’s user interface reveals the two spikes in outbound emails that were sent out by compromised company accounts.

Thanks to Darktrace analyst Emma Foulger for her insights on the above threat find.

Learn more about the threats facing logistics providers

Darktrace model detections:

  • SaaS / Compliance / New Email Rule
  • SaaS / Unusual Login and New Email Rule
  • Antigena Email models included
  • Unusual / Unusual Login Location and New Unknown Link
  • Link / Account Hijack Link
  • Link / Outlook Hijack
  • Internal Compromise / Recipient Surge from Unusual Login Location (outbound emails)
  • Internal Compromise / Recipient Surge with Suspicious Content (outbound emails)

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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.
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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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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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