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March 17, 2021

AI Neutralized Hafnium-Inspired Cyber-Attacks

Learn from this real-life scenario where Darktrace detected a ProxyLogon vulnerability and took action to protect Exchange servers. Read 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
Max Heinemeyer
Global Field CISO
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17
Mar 2021

On March 11 and 12, 2021, Darktrace detected multiple attempts by a broad campaign to attack vulnerable servers in customer environments. The campaign targeted Internet-facing Microsoft Exchange servers, exploiting the recently discovered ProxyLogon vulnerability (CVE-2021-26855).

While this exploit was initially attributed to a group known as Hafnium, Microsoft has announced that the vulnerability is also being rapidly weaponized by other threat actors. These new, unattributed campaigns, which have never been seen before, have been disrupted by Cyber AI in real time.

Hafnium copycats

As soon as a vulnerability is made public it is common for there to be an influx of attacks as hackers capitalize on the chaos and attempt to compromise vulnerable networks.

Patches are rapidly reverse-engineered by hackers once they have been published by the vendor, leading to mass high-impact exploits. At the same time, the offensive tooling trickles down from the first adopters, such as nation-state actors, to ransomware gangs and other opportunistic attackers. Darktrace has observed this exact phenomenon as a result of Hafnium’s attacks against vulnerable Microsoft Exchange email servers this month.

Exchange servers attacked: AI analysis

Cyber AI has observed threat actors attempting to download and install malware using ProxyLogon as the initial attack vector. For customers with Autonomous Response, the malicious payload was intercepted at this point, stopping the attack before any developments.

In other Darktrace customer environments, the Darktrace Immune System identified and alerted on every stage of the attack. Generally, the malware has been observed acting as a generic backdoor, without much follow-up activity. Various forms of command and control (C2) channels were detected, including Telegra[.]ph. In a few intrusions, the attackers installed cryptocurrency miners.

Once a foothold has been established in the digital environment, it is likely that the actors will begin a hands-on-keyboard attack, exfiltrating data, moving laterally, or deploying ransomware.

Figure 1: Timeline of a typical ProxyLogon exploit

After the ProxyLogon vulnerability was exploited, the Exchange servers reached out to the malicious domain microsoftsoftwaredownload[.]com, utilizing a PowerShell User Agent. Darktrace flagged this anomalous behavior as the particular User Agent had never been used before by the Exchange server, let alone to access a malicious domain which had never been observed in the network.

Figure 2: Darktrace revealing an anomalous PowerShell connection

The malware executable was masqueraded as a ZIP file, further trying to obfuscate the attack. Darktrace identified this highly anomalous file download and the masqueraded file.

Figure 3: Darktrace revealing key information around the anomalous file download

In some cases, Darktrace AI also observed cryptocurrency mining seconds or minutes after the initial malware download.

Figure 4: Darktrace’s Crypto Currency Mining model is breached

In terms of C2 traffic, Darktrace has observed various potential channels. Around the time of the malware download, some of the Exchange servers began to beacon out to several external destinations using unusual SSL or TLS encrypted connections.

  • Telegra[.]ph — popular messenger application
  • dev.opendrive[.]com — cloud storage service
  • od[.]lk — cloud storage service

In this case, Darktrace recognized that none of these three external domains had ever been contacted before by anybody in the organization, let alone in a beaconing fashion. The fact that these communications started around the same time as the malware downloads strongly suggests a correlation. Darktrace’s Cyber AI Analyst automatically began an investigation into the incident, stitching together these events into one coherent narrative.

Investigating with AI

Cyber AI Analyst then automatically created a summary incident report about the activity, covering the malware download as well as the various C2 channels observed.

Figure 5: Cyber AI Analyst automatically generating a high-level incident summary

Looking at an infected Exchange server ([REDACTED].local) from a birds-eye perspective shows that Darktrace created various alerts when the attack hit. Every one of the colored dots in the graph below represents a major anomaly detected by Darktrace.

Figure 6: Darktrace reveals the anomalous number of connections and subsequent model breaches

This activity was prioritized as the most urgent incident in Cyber AI Analyst among a full week’s worth of data. In this particular organization, there were only four incidents for that week in total in Cyber AI Analyst. Such precise and clear alerting allows security teams to immediately understand the top threats facing their digital environment, without being overwhelmed by unnecessary alerts and false positives.

Machine-speed response

For customers with Darktrace Antigena, Antigena autonomously acted to block all outgoing traffic to malicious external endpoints on the relevant ports. This behavior is held for several hours to interrupt the threat actor from escalating the attack, while giving security teams time to react and remediate.

Antigena responded within seconds of the attack starting, effectively containing the attack in its earliest stage – without interrupting regular business activity (emails could still be sent and received), and despite this being a zero-day campaign.

Figure 7: Darktrace Antigena autonomously responds

Catching a zero-day exploit

This is not the first time Darktrace has stopped an attack leveraging a zero-day or a freshly released n-day vulnerability. Back in March 2020, Darktrace detected APT41 exploiting the Zoho ManageEngine vulnerability, two weeks before public attribution.

It is highly likely that there will be more cyber-criminals exploiting ProxyLogon in the wake of Hafnium. And while the recent Exchange server vulnerabilities were today’s threat, next time it might be a software or hardware supply chain attack, or a different zero-day. Novel threats are emerging every week. In this climate we now find ourselves in, where ‘known unknowns’ which are difficult or impossible to pre-define are the new norm, we need to be more adaptable and proactive than ever.

As soon as an attacker begins to exhibit unusual activity, Darktrace AI will detect it, even if there is no threat intelligence associated with the attack. This is where Darktrace works best, autonomously detecting, investigating and responding to advanced and never-before-seen threats in real time.

Learn more about the Darktrace Immune System

Example Darktrace model detections:

  • Antigena / Network / Compliance / Antigena Crypto Currency Mining Block
  • Compliance / Crypto Currency Mining Activity
  • Antigena / Network / Significant Anomaly / Antigena Breaches Over Time Block
  • Anomalous Connection / Suspicious Expired SSL
  • Antigena / Network / Significant Anomaly / Antigena Significant Anomaly from Client Block
  • Antigena / Network / Significant Anomaly / Antigena Enhanced Monitoring from Client Block
  • Device / Initial Breach Chain Compromise
  • Antigena / Network / Significant Anomaly / Antigena Breaches Over Time Block
  • Anomalous File / Masqueraded File Transfer
  • Anomalous File / EXE from Rare External Location
  • Antigena / Network / External Threat / Antigena Suspicious File Block
  • Antigena / Network / External Threat / Antigena File then New Outbound Block
  • Antigena / Network / Significant Anomaly / Antigena Controlled and Model Breach
  • Anomalous File / Internet Facing System File Download
  • Device / New PowerShell User Agent
  • Anomalous File / Multiple EXE from Rare External Locations
  • Anomalous Connection / Powershell to Rare External


Inside the SOC
Darktrace cyber analysts are world-class experts in threat intelligence, threat hunting and incident response, and provide 24/7 SOC support to thousands of Darktrace customers around the globe. Inside the SOC is exclusively authored by these experts, providing analysis of cyber incidents and threat trends, based on real-world experience in the field.
Written by
Max Heinemeyer
Global Field CISO

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December 18, 2025

Why organizations are moving to label-free, behavioral DLP for outbound email

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Why outbound email DLP needs reinventing

In 2025, the global average cost of a data breach fell slightly — but remains substantial at USD 4.44 million (IBM Cost of a Data Breach Report 2025). The headline figure hides a painful reality: many of these breaches stem not from sophisticated hacks, but from simple human error: mis-sent emails, accidental forwarding, or replying with the wrong attachment. Because outbound email is a common channel for sensitive data leaving an organization, the risk posed by everyday mistakes is enormous.

In 2025, 53% of data breaches involved customer PII, making it the most commonly compromised asset (IBM Cost of a Data Breach Report 2025). This makes “protection at the moment of send” essential. A single unintended disclosure can trigger compliance violations, regulatory scrutiny, and erosion of customer trust –consequences that are disproportionate to the marginal human errors that cause them.

Traditional DLP has long attempted to mitigate these impacts, but it relies heavily on perfect labelling and rigid pattern-matching. In reality, data loss rarely presents itself as a neat, well-structured pattern waiting to be caught – it looks like everyday communication, just slightly out of context.

How data loss actually happens

Most data loss comes from frustratingly familiar scenarios. A mistyped name in auto-complete sends sensitive data to the wrong “Alex.” A user forwards a document to a personal Gmail account “just this once.” Someone shares an attachment with a new or unknown correspondent without realizing how sensitive it is.

Traditional, content-centric DLP rarely catches these moments. Labels are missing or wrong. Regexes break the moment the data shifts formats. And static rules can’t interpret the context that actually matters – the sender-recipient relationship, the communication history, or whether this behavior is typical for the user.

It’s the everyday mistakes that hurt the most. The classic example: the Friday 5:58 p.m. mis-send, when auto-complete selects Martin, a former contractor, instead of Marta in Finance.

What traditional DLP approaches offer (and where gaps remain)

Most email DLP today follows two patterns, each useful but incomplete.

  • Policy- and label-centric DLP works when labels are correct — but content is often unlabeled or mislabeled, and maintaining classification adds friction. Gaps appear exactly where users move fastest
  • Rule and signature-based approaches catch known patterns but miss nuance: human error, new workflows, and “unknown unknowns” that don’t match a rule

The takeaway: Protection must combine content + behavior + explainability at send time, without depending on perfect labels.

Your technology primer: The three pillars that make outbound DLP effective

1) Label-free (vs. data classification)

Protects all content, not just what’s labeled. Label-free analysis removes classification overhead and closes gaps from missing or incorrect tags. By evaluating content and context at send time, it also catches misdelivery and other payload-free errors.

  • No labeling burden; no regex/rule maintenance
  • Works when tags are missing, wrong, or stale
  • Detects misdirected sends even when labels look right

2) Behavioral (vs. rules, signatures, threat intelligence)

Understands user behavior, not just static patterns. Behavioral analysis learns what’s normal for each person, surfacing human error and subtle exfiltration that rules can’t. It also incorporates account signals and inbound intel, extending across email and Teams.

  • Flags risk without predefined rules or IOCs
  • Catches misdelivery, unusual contacts, personal forwards, odd timing/volume
  • Blends identity and inbound context across channels

3) Proprietary DSLM (vs. generic LLM)

Optimized for precise, fast, explainable on-send decisions. A DSLM understands email/DLP semantics, avoids generative risks, and stays auditable and privacy-controlled, delivering intelligence reliably without slowing mail flow.

  • Low-latency, on-send enforcement
  • Non-generative for predictable, explainable outcomes
  • Governed model with strong privacy and auditability

The Darktrace approach to DLP

Darktrace / EMAIL – DLP stops misdelivery and sensitive data loss at send time using hold/notify/justify/release actions. It blends behavioral insight with content understanding across 35+ PII categories, protecting both labeled and unlabeled data. Every action is paired with clear explainability: AI narratives show exactly why an email was flagged, supporting analysts and helping end-users learn. Deployment aligns cleanly with existing SOC workflows through mail-flow connectors and optional Microsoft Purview label ingestion, without forcing duplicate policy-building.

Deployment is simple: Microsoft 365 routes outbound mail to Darktrace for real-time, inline decisions without regex or rule-heavy setup.

A buyer’s checklist for DLP solutions

When choosing your DLP solution, you want to be sure that it can deliver precise, explainable protection at the moment it matters – on send – without operational drag.  

To finish, we’ve compiled a handy list of questions you can ask before choosing an outbound DLP solution:

  • Can it operate label free when tags are missing or wrong? 
  • Does it truly learn per user behavior (no shortcuts)? 
  • Is there a domain specific model behind the content understanding (not a generic LLM)? 
  • Does it explain decisions to both analysts and end users? 
  • Will it integrate with your label program and SOC workflows rather than duplicate them? 

For a deep dive into Darktrace’s DLP solution, check out the full solution brief.

[related-resource]

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About the author
Carlos Gray
Senior Product Marketing Manager, Email

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December 17, 2025

Beyond MFA: Detecting Adversary-in-the-Middle Attacks and Phishing with Darktrace

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What is an Adversary-in-the-middle (AiTM) attack?

Adversary-in-the-Middle (AiTM) attacks are a sophisticated technique often paired with phishing campaigns to steal user credentials. Unlike traditional phishing, which multi-factor authentication (MFA) increasingly mitigates, AiTM attacks leverage reverse proxy servers to intercept authentication tokens and session cookies. This allows attackers to bypass MFA entirely and hijack active sessions, stealthily maintaining access without repeated logins.

This blog examines a real-world incident detected during a Darktrace customer trial, highlighting how Darktrace / EMAILTM and Darktrace / IDENTITYTM identified the emerging compromise in a customer’s email and software-as-a-service (SaaS) environment, tracked its progression, and could have intervened at critical moments to contain the threat had Darktrace’s Autonomous Response capability been enabled.

What does an AiTM attack look like?

Inbound phishing email

Attacks typically begin with a phishing email, often originating from the compromised account of a known contact like a vendor or business partner. These emails will often contain malicious links or attachments leading to fake login pages designed to spoof legitimate login platforms, like Microsoft 365, designed to harvest user credentials.

Proxy-based credential theft and session hijacking

When a user clicks on a malicious link, they are redirected through an attacker-controlled proxy that impersonates legitimate services.  This proxy forwards login requests to Microsoft, making the login page appear legitimate. After the user successfully completes MFA, the attacker captures credentials and session tokens, enabling full account takeover without the need for reauthentication.

Follow-on attacks

Once inside, attackers will typically establish persistence through the creation of email rules or registering OAuth applications. From there, they often act on their objectives, exfiltrating sensitive data and launching additional business email compromise (BEC) campaigns. These campaigns can include fraudulent payment requests to external contacts or internal phishing designed to compromise more accounts and enable lateral movement across the organization.

Darktrace’s detection of an AiTM attack

At the end of September 2025, Darktrace detected one such example of an AiTM attack on the network of a customer trialling Darktrace / EMAIL and Darktrace / IDENTITY.

In this instance, the first indicator of compromise observed by Darktrace was the creation of a malicious email rule on one of the customer’s Office 365 accounts, suggesting the account had likely already been compromised before Darktrace was deployed for the trial.

Darktrace / IDENTITY observed the account creating a new email rule with a randomly generated name, likely to hide its presence from the legitimate account owner. The rule marked all inbound emails as read and deleted them, while ignoring any existing mail rules on the account. This rule was likely intended to conceal any replies to malicious emails the attacker had sent from the legitimate account owner and to facilitate further phishing attempts.

Darktrace’s detection of the anomalous email rule creation.
Figure 1: Darktrace’s detection of the anomalous email rule creation.

Internal and external phishing

Following the creation of the email rule, Darktrace / EMAIL observed a surge of suspicious activity on the user’s account. The account sent emails with subject lines referencing payment information to over 9,000 different external recipients within just one hour. Darktrace also identified that these emails contained a link to an unusual Google Drive endpoint, embedded in the text “download order and invoice”.

Darkrace’s detection of an unusual surge in outbound emails containing suspicious content, shortly following the creation of a new email rule.
Figure 2: Darkrace’s detection of an unusual surge in outbound emails containing suspicious content, shortly following the creation of a new email rule.
Darktrace / EMAIL’s detection of the compromised account sending over 9,000 external phishing emails, containing an unusual Google Drive link.
Figure 3: Darktrace / EMAIL’s detection of the compromised account sending over 9,000 external phishing emails, containing an unusual Google Drive link.

As Darktrace / EMAIL flagged the message with the ‘Compromise Indicators’ tag (Figure 2), it would have been held automatically if the customer had enabled default Data Loss Prevention (DLP) Action Flows in their email environment, preventing any external phishing attempts.

Figure 4: Darktrace / EMAIL’s preview of the email sent by the offending account.
Figure 4: Darktrace / EMAIL’s preview of the email sent by the offending account.

Darktrace analysis revealed that, after clicking the malicious link in the email, recipients would be redirected to a convincing landing page that closely mimicked the customer’s legitimate branding, including authentic imagery and logos, where prompted to download with a PDF named “invoice”.

Figure 5: Download and login prompts presented to recipients after following the malicious email link, shown here in safe view.

After clicking the “Download” button, users would be prompted to enter their company credentials on a page that was likely a credential-harvesting tool, designed to steal corporate login details and enable further compromise of SaaS and email accounts.

Darktrace’s Response

In this case, Darktrace’s Autonomous Response was not fully enabled across the customer’s email or SaaS environments, allowing the compromise to progress,  as observed by Darktrace here.

Despite this, Darktrace / EMAIL’s successful detection of the malicious Google Drive link in the internal phishing emails prompted it to suggest ‘Lock Link’, as a recommended action for the customer’s security team to manually apply. This action would have automatically placed the malicious link behind a warning or screening page blocking users from visiting it.

Autonomous Response suggesting locking the malicious Google Drive link sent in internal phishing emails.
Figure 6: Autonomous Response suggesting locking the malicious Google Drive link sent in internal phishing emails.

Furthermore, if active in the customer’s SaaS environment, Darktrace would likely have been able to mitigate the threat even earlier, at the point of the first unusual activity: the creation of a new email rule. Mitigative actions would have included forcing the user to log out, terminating any active sessions, and disabling the account.

Conclusion

AiTM attacks represent a significant evolution in credential theft techniques, enabling attackers to bypass MFA and hijack active sessions through reverse proxy infrastructure. In the real-world case we explored, Darktrace’s AI-driven detection identified multiple stages of the attack, from anomalous email rule creation to suspicious internal email activity, demonstrating how Autonomous Response could have contained the threat before escalation.

MFA is a critical security measure, but it is no longer a silver bullet. Attackers are increasingly targeting session tokens rather than passwords, exploiting trusted SaaS environments and internal communications to remain undetected. Behavioral AI provides a vital layer of defense by spotting subtle anomalies that traditional tools often miss

Security teams must move beyond static defenses and embrace adaptive, AI-driven solutions that can detect and respond in real time. Regularly review SaaS configurations, enforce conditional access policies, and deploy technologies that understand “normal” behavior to stop attackers before they succeed.

Credit to David Ison (Cyber Analyst), Bertille Pierron (Solutions Engineer), Ryan Traill (Analyst Content Lead)

Appendices

Models

SaaS / Anomalous New Email Rule

Tactic – Technique – Sub-Technique  

Phishing - T1566

Adversary-in-the-Middle - T1557

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