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June 3, 2024

The Price of Admission: Countering Stolen Credentials with Darktrace

This blog examines a network compromise that stemmed from the purchase of leaked credentials from the dark web. Credentials purchased from dark web marketplaces allow unauthorized access to internal systems. Such access can be used to exfiltrate data, disrupt operations, or deploy malware.
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
Charlotte Thompson
Cyber Analyst
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03
Jun 2024

Using leaked credentials to gain unauthorized access

Dark web marketplaces selling sensitive data have increased accessibility for malicious actors, similar to Ransomware-as-a-Service (RaaS), lowering the barrier to entry usually associated with malicious activity. By utilizing leaked credentials, malicious actors can easily gain unauthorized access to accounts and systems which they can leverage to carry out malicious activities like data exfiltration or malware deployment.

Usage of leaked credentials by malicious actors is a persistent concern for both organizations and security providers. Google Cloud’s ‘H1 2024 Threat Horizons Report’ details that initial access seen in 2.9% of cloud compromises observed on Google Cloud resulted from leaked credential usage [1], with the ‘IBM X-Force Threat Intelligence Index 2024’ reporting 71% year-on-year increase in cyber-attacks which utilize stolen or compromised credentials [2].

Darktrace coverage of leaked credentials

In early 2024, one Darktrace customer was compromised by a malicious actor after their internal credentials had been leaked on the dark web. Subsequent attack phases were detected by Darktrace/Network and the customer was alerted to the suspicious activity via the Proactive Threat Notification (PTN) service, following an investigation by Darktrace’s Security Operation Center (SOC).

Darktrace detected a device on the network of a customer in the US carrying out a string of anomalous activity indicative of network compromise. The device was observed using a new service account to authenticate to a Virtual Private Network (VPN) server, before proceeding to perform a range of suspicious activity including internal reconnaissance and lateral movement.

Malicious actors seemingly gained access to a previously unused service account for which they were able to set up multi-factor authentication (MFA) to access the VPN. As this MFA setup was made possible by the configuration of the customer’s managed service provider (MSP), the initial access phase of the attack fell outside of Darktrace’s purview.

Unfortunately for the customer in this case, Darktrace RESPOND™ was not enabled on the network at the time of the attack. Had RESPOND been active, it would have been able to autonomously act against the malicious activity by disabling users, strategically blocking suspicious connections and limiting devices to their expected patterns of activity.

Attack timeline of leaked credentials spotted by darktrace

Network Scanning Activity

On February 22, 2024, Darktrace detected the affected device performing activity indicative of network scanning, namely initiating connections on multiple ports, including ports 80, 161 389 and 445, to other internal devices. While many of these internal connection attempts were unsuccessful, some successful connections were observed.

Devices on a network can gather information about other internal devices by performing network scanning activity. Defensive scanning can be used to support network security, allowing internal security teams to discover vulnerabilities and potential entry points that require their attention, however attackers are also able to take advantage of such information, such as open ports and services available on internal devices, with offensive scanning.

Brute Force Login Attempts

Darktrace proceeded to identify the malicious actor attempting to access a previously unused service account for which they were able to successfully establish MFA to access the organization’s VPN. As the customer’s third-party MSP had been configured to allow all users to login to the organization’s VPN using MFA, this login was successful. Moreover, the service account had never previously been used and MFA and never been established, allowing the attacker to leverage it for their own nefarious means.

Darktrace/Network identified the attacker attempting to authenticate over the Kerberos protocol using a total of 30 different usernames, of which two were observed successfully authenticating. There was a total of 6 successful Kerberos logins identified from two different credentials.  Darktrace also observed over 100 successful NTLM attempts from the same device for multiple usernames including “Administrator” and “mail”. These credentials were later confirmed by the customer to have been stolen and leaked on the dark web.

Advanced Search query results showing the usernames that successfully authenticated via NTLM.
Figure 1: Advanced Search query results showing the usernames that successfully authenticated via NTLM.

Even though MFA requirements had been satisfied when the threat actor accessed the organization’s VPN, Darktrace recognized that this activity represented a deviation from its previously learned behavior.

Malicious actors frequently attempt to gain unauthorized access to accounts and internal systems by performing login attempts using multiple possible usernames and passwords. This type of brute-force activity is typically accomplished using computational power via the use of software or scripts to attempt different username/password combinations until one is successful.

By purchasing stolen credentials from dark web marketplaces, attackers are able to significantly increase the success rate of brute-force attacks and, if they do gain access, they can easily act on their objectives, be that exfiltrating sensitive data or moving through their target networks to further the compromise.

Share Enumeration

Around 30 minutes after the initial network scanning activity, the compromised device was observed performing SMB enumeration using one of the aforementioned accounts. Darktrace understood that this activity was suspicious as the device had never previously been used to perform SMB activity and had not been tagged as a security device.

Darktrace/Network identifying the suspicious SMB enumeration performed by the compromised device.
Figure 2: Darktrace/Network identifying the suspicious SMB enumeration performed by the compromised device.

Such enumeration can be used by malicious actors to gain insights into the structures and configurations of a target device, view permissions associated with shared resources, and also view general identifying information about the system.

Darktrace further identified that the device connected to the named pipe “srvsvc”. By enumerating over srvsvc, a threat actor is able to request a list of all available SMB shares on a destination device, enabling further data gathering as part of network reconnaissance. Srvsvc also provides access to remote procedure call (RPC) for various services on a destination device.

At this stage, a Darktrace/Network Enhanced Monitoring model was triggered for lateral movement activity taking place on the customer’s network. As this particular customer was subscribed to the PTN service, the Enhanced Monitoring model alert was promptly triaged and investigated by the Darktrace SOC. The customer was alerted to the emerging activity and given full details of the incident and the SOC team’s investigation.

Attack and Reconnaissance Tool Usage

A few minutes later, Darktrace observed the device making a connection with a user agent associated with the Nmap network scanning tool, “Mozilla/5.0 (compatible; Nmap Scripting Engine; https://nmap.org/book/nse[.]html)”. While these tools are often used legitimately by an organization’s security team, they can also be used maliciously by attackers to exploit vulnerabilities that attackers may have unearthed during earlier reconnaissance activity.

As such services are often seen as normal network traffic, attackers can often use them to bypass traditional security measures. Darktrace’s Self-Learning AI, however, was able to recognize that the affected device was not a security device and therefore not expected to carry out such activity, even if it was using a legitimate Nmap service.

Darktrace/Network identifying the compromised device using the Nmap scanning tool.
Figure 3: Darktrace/Network identifying the compromised device using the Nmap scanning tool.

Further Lateral Movement

Following this suspicious Nmap usage, Darktrace observed a range of additional anomalous SMB activity from the aforementioned compromised account. The affected device attempted to establish almost 900 SMB sessions, as well as performing 65 unusual file reads from 29 different internal devices and over 300 file deletes for the file “delete.me” from over 100 devices using multiple paths, including ADMIN$, C$, print$.

Darktrace also observed the device making several DCE-RPC connections associated with Active Directory Domain enumeration, including DRSCrackNames and DRSGetNCChanges; a total of more than 1000 successful DCE-RPC connection were observed to a domain controller.

As this customer did not have Darktrace/Network's autonomous response deployed on their network, the above detailed lateral movement and network reconnaissance activity was allowed to progress unfettered, until Darktrace’s SOC alerted the customer’s security team to take urgent action. The customer also received follow-up support through Darktrace’s Ask the Expert (ATE) service, allowing them to contact the analyst team directly for further details and support on the incident.

Thanks to this early detection, the customer was able to quickly identify and disable affected user accounts, effectively halting the attack and preventing further escalation.

Conclusions

Given the increasing trend of ransomware attackers exfiltrating sensitive data for double extortion and the rise of information stealers, stolen credentials are commonplace across dark web marketplaces. Malicious actors can exploit these leaked credentials to drastically lower the barrier to entry associated with brute-forcing access to their target networks.

While implementing well-configured MFA and enforcing regular password changes can help protect organizations, these measures alone may not be enough to fully negate the advantage attackers gain with stolen credentials.

In this instance, an attacker used leaked credentials to compromise an unused service account, allowing them to establish MFA and access the customer’s VPN. While this tactic may have allowed the attacker to evade human security teams and traditional security tools, Darktrace’s AI detected the unusual use of the account, indicating a potential compromise despite the organization’s MFA requirements being met. This underscores the importance of adopting an intelligent decision maker, like Darktrace, that is able to identify and respond to anomalies beyond standard protective measures.

Credit to Charlotte Thompson, Cyber Security Analyst, Ryan Traill, Threat Content Lead

Appendices

Darktrace DETECT Model Coverage

-       Device / Suspicious SMB Scanning Activity (Model Alert)

-       Device / ICMP Address Scan (Model Alert)

-       Device / Network Scan (Model Alert)

-       Device / Suspicious LDAP Search Operation (Model Alert)

-       User / Kerberos Username Brute Force (Model Alert)

-       Device / Large Number of Model Breaches (Model Alert)

-       Anomalous Connection / SMB Enumeration (Model Alert)

-       Device / Multiple Lateral Movement Model Breaches (Enhanced Monitoring Model Alert)

-       Device / Possible SMB/NTLM Reconnaissance (Model Alert)

-       Anomalous Connection / Possible Share Enumeration Activity (Model Alert)

-       Device / Attack and Recon Tools (Model Alert)

MITRE ATT&CK Mapping

Tactic – Technique - Code

INITIAL ACCESS - Hardware Additions     -T1200

DISCOVERY - Network Service Scanning -T1046

DISCOVERY - Remote System Discovery - T1018

DISCOVERY - Domain Trust Discovery      - T1482

DISCOVERY - File and Directory Discovery - T1083

DISCOVERY - Network Share Discovery - T1135

RECONNAISSANCE - Scanning IP Blocks - T1595.001

RECONNAISSANCE - Vulnerability Scanning - T1595.002

RECONNAISSANCE - Client Configurations - T1592.004

RECONNAISSANCE - IP Addresses - T1590.005

CREDENTIAL ACCESS - Brute Force - T1110

LATERAL MOVEMENT - Exploitation of Remote Services -T1210

References

  1. 2024 Google Cloud Threat Horizons Report
    https://services.google.com/fh/files/misc/threat_horizons_report_h12024.pdf
  2. IBM X-Force Threat Intelligence Index 2024
    https://www.ibm.com/reports/threat-intelligence
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
Charlotte Thompson
Cyber Analyst

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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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About the author
David Ison
Cyber Analyst
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