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September 30, 2024

Business Email Compromise (BEC) in the Age of AI

Generative AI tools have increased the risk of BEC, and traditional cybersecurity defenses struggle to stay ahead of the growing speed, scale, and sophistication of attacks. Only multilayered, defense-in-depth strategies can counter the AI-powered BEC threat.
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
Carlos Gray
Senior Product Marketing Manager, Email
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30
Sep 2024

As people continue to be the weak link in most organizations’ cybersecurity practices, the growing use of generative AI tools in cyber-attacks makes email, their primary communications channel, a more compelling target than ever. The risk associated with Business Email Compromise (BEC) in particular continues to rise as generative AI tools equip attackers to build and launch social engineering and phishing campaigns with greater speed, scale, and sophistication.

What is BEC?

BEC is defined in different ways, but generally refers to cyber-attacks in which attackers abuse email — and users’ trust — to trick employees into transferring funds or divulging sensitive company data.

Unlike generic phishing emails, most BEC attacks do not rely on “spray and pray” dissemination or on users’ clicking bogus links or downloading malicious attachments. Instead, modern BEC campaigns use a technique called “pretexting.”

What is pretexting?

Pretexting is a more specific form of phishing that describes an urgent but false situation — the pretext — that requires the transfer of funds or revelation of confidential data.  

This type of attack, and therefore BEC, is dominating the email threat landscape. As reported in Verizon’s 2024 Data Breach Investigation Report, recently there has been a “clear overtaking of pretexting as a more likely social action than phishing.” The data shows pretexting, “continues to be the leading cause of cybersecurity incidents (accounting for 73% of breaches)” and one of “the most successful ways of monetizing a breach.”

Pretexting and BEC work so well because they exploit humans’ natural inclination to trust the people and companies they know. AI compounds the risk by making it easier for attackers to mimic known entities and harder for security tools and teams – let alone unsuspecting recipients of routine emails – to tell the difference.

BEC attacks now incorporate AI

With the growing use of AI by threat actors, trends point to BEC gaining momentum as a threat vector and becoming harder to detect. By adding ingenuity, machine speed, and scale, generative AI tools like OpenAI’s ChatGPT give threat actors the ability to create more personalized, targeted, and convincing emails at scale.

In 2023, Darktrace researchers observed a 135% rise in ‘novel social engineering attacks’ across Darktrace / EMAIL customers, corresponding with the widespread adoption of ChatGPT.

Large Language Models (LLMs) like ChatGPT can draft believable messages that feel like emails that target recipients expect to receive. For example, generative AI tools can be used to send fake invoices from vendors known to be involved with well-publicized construction projects. These messages also prove harder to detect as AI automatically:

  • Avoids misspellings and grammatical errors
  • Creates multiple variations of email text  
  • Translates messages that read well in multiple languages
  • And accomplishes additional, more targeted tactics

AI creates a force multiplier that allows primitive mass-mail campaigns to evolve into sophisticated automated attacks. Instead of spending weeks studying the target to craft an effective email, cybercriminals might only spend an hour or two and achieve a better result.  

Challenges of detecting AI-powered BEC attacks

Rules-based detections miss unknown attacks

One major challenge comes from the fact that rules based on known attacks have no basis to deny new threats. While native email security tools defend against known attacks, many modern BEC attacks use entirely novel language and can omit payloads altogether. Instead, they rely on pure social engineering or bide their time until security tools recognize the new sender as a legitimate contact.  

Most defensive AI can’t keep pace with attacker innovation

Security tools might focus on the meaning of an email’s text in trying to recognize a BEC attack, but defenders still end up in a rules and signature rat race. Some newer Integrated Cloud Email Security (ICES) vendors attempt to use AI defensively to improve the flawed approach of only looking for exact matches. Employing data augmentation to identify similar-looking emails helps to a point but not enough to outpace novel attacks built with generative AI.

What tools can stop BEC?

A modern defense-in-depth strategy must use AI to counter the impact of AI in the hands of attackers. As found in our 2024 State of AI Cybersecurity Report, 96% of survey participants believe AI-driven security solutions are a must have for countering AI-powered threats.

However, not all AI tools are the same. Since BEC attacks continue to change, defensive AI-powered tools should focus less on learning what attacks look like, and more on learning normal behavior for the business. By understanding expected behavior on the company’s side, the security solution will be able to recognize anomalous and therefore suspicious activity, regardless of the word choice or payload type.  

To combat the speed and scale of new attacks, an AI-led BEC defense should spot novel threats.

Darktrace / EMAIL™ can do that.  

Self-Learning AI builds profiles for every email user, including their relationships, tone and sentiment, content, and link sharing patterns. Rich context helps in understanding how people communicate and identifying deviations from the normal routine to determine what does and does not belong in an individual’s inbox and outbox.  

Other email security vendors may claim to use behavioral AI and unsupervised machine learning in their products, but their AI are still pre-trained with historical data or signatures to recognize malicious activity, rather than demonstrating a true learning process. Darktrace’s Self Learning-AI truly learns from the organization in which it is installed, allowing it to detect unknown and novel vectors that other security tools are not yet trained on.

Because Darktrace understands the human behind email communications rather than knowledge of past attacks, Darktrace / EMAIL can stop the most sophisticated and evolving email security risks. It enhances your native email security by leveraging business-centric behavioral anomaly detection across inbound, outbound, and lateral messages in both email and Teams.

This unique approach quickly identifies sophisticated threats like BEC, ransomware, phishing, and supply chain attacks without duplicating existing capabilities or relying on traditional rules, signatures, and payload analysis.  

The power of Darktrace’s AI can be seen in its speed and adaptability: Darktrace / EMAIL blocks the most novel threats up to 13 days faster than traditional security tools.

Learn more about AI-led BEC threats, how these threats extend beyond the inbox, and how organizations can adopt defensive AI to outpace attacker innovation in the white paper “Beyond the Inbox: A Guide to Preventing Business Email Compromise.”

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
Carlos Gray
Senior Product Marketing Manager, Email

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October 30, 2025

WSUS Exploited: Darktrace’s Analysis of Post-Exploitation Activities Related to CVE-2025-59287

WSUS Exploited: Darktrace’s Analysis of Post-Exploitation Activities Related to CVE-2025-59287Default blog imageDefault blog image

Introduction

On October 14, 2025, Microsoft disclosed a new critical vulnerability affecting the Windows Server Update Service (WSUS), CVE-2025-59287.  Exploitation of the vulnerability could allow an unauthenticated attacker to remotely execute code [1][6].

WSUS allows for centralized distribution of Microsoft product updates [3]; a server running WSUS is likely to have significant privileges within a network making it a valuable target for threat actors. While WSUS servers are not necessarily expected to be open to the internet, open-source intelligence (OSINT) has reported  thousands of publicly exposed instances that may be vulnerable to exploitation [2].

Microsoft’s initial ‘Patch Tuesday’ update for this vulnerability did not fully mitigate the risk, and so an out-of-band update followed on October 23 [4][5] . Widespread exploitation of this vulnerability started to be observed shortly after the security update [6], prompting CISA to add CVE-2025-59287 to its Known Exploited Vulnerability Catalog (KEV) on October 24 [7].

Attack Overview

The Darktrace Threat Research team have recently identified multiple potential cases of CVE-2025-59287 exploitation, with two detailed here. While the likely initial access method is consistent across the cases, the follow-up activities differed, demonstrating the variety in which such a CVE can be exploited to fulfil each attacker’s specific goals.

The first signs of suspicious activity across both customers were detected by Darktrace on October 24, the same day this vulnerability was added to CISA’s KEV. Both cases discussed here involve customers based in the United States.

Case Study 1

The first case, involving a customer in the Information and Communication sector, began with an internet-facing device making an outbound connection to the hostname webhook[.]site. Observed network traffic indicates the device was a WSUS server.

OSINT has reported abuse of the workers[.]dev service in exploitation of CVE-2025-59287, where enumerated network information gathered through running a script on the compromised device was exfiltrated using this service [8].

In this case, the majority of connectivity seen to webhook[.]site involved a PowerShell user agent; however, cURL user agents were also seen with some connections taking the form of HTTP POSTs. This connectivity appears to align closely with OSINT reports of CVE-2025-59287 post-exploitation behaviour [8][9].

Connections to webhook[.]site continued until October 26. A single URI was seen consistently until October 25, after which the connections used a second URI with a similar format.

Later on October 26, an escalation in command-and-control (C2) communication appears to have occurred, with the device starting to make repeated connections to two rare workers[.]dev subdomains (royal-boat-bf05.qgtxtebl.workers[.]dev & chat.hcqhajfv.workers[.]dev), consistent with C2 beaconing. While workers[.]dev is associated with the legitimate Cloudflare Workers service, the service is commonly abused by malicious actors for C2 infrastructure. The anomalous nature of the connections to both webhook[.]site and workers[.]dev led to Darktrace generating multiple alerts including high-fidelity Enhanced Monitoring alerts and alerts for Darktrace’s Autonomous Response.

Infrastructure insight

Hosted on royal-boat-bf05.qgtxtebl.workers[.]dev is a Microsoft Installer file (MSI) named v3.msi.

Screenshot of v3.msi content.
Figure 1: Screenshot of v3.msi content.

Contained in the MSI file is two Cabinet files named “Sample.cab” and “part2.cab”. After extracting the contents of the cab files, a file named “Config” and a binary named “ServiceEXE”. ServiceEXE is the legitimate DFIR tool Velociraptor, and “Config” contains the configuration details, which include chat.hcqhajfv.workers[.]dev as the server_url, suggesting that Velociraptor is being used as a tunnel to the C2. Additionally, the configuration points to version 0.73.4, a version of Velociraptor that is vulnerable to CVE-2025-6264, a privilege escalation vulnerability.

 Screenshot of Config file.
Figure 2: Screenshot of Config file.

Velociraptor, a legitimate security tool maintained by Rapid7, has been used recently in malicious campaigns. A vulnerable version of tool has been used by threat actors for command execution and endpoint takeover, while other campaigns have used Velociraptor to create a tunnel to the C2, similar to what was observed in this case [10] .

The workers[.]dev communication continued into the early hours of October 27. The most recent suspicious behavior observed on the device involved an outbound connection to a new IP for the network - 185.69.24[.]18/singapure - potentially indicating payload retrieval.

The payload retrieved from “/singapure” is a UPX packed Windows binary. After unpacking the binary, it is an open-source Golang stealer named “Skuld Stealer”. Skuld Stealer has the capabilities to steal crypto wallets, files, system information, browser data and tokens. Additionally, it contains anti-debugging and anti-VM logic, along with a UAC bypass [11].

A timeline outlining suspicious activity on the device alerted by Darktrace.
Figure 3: A timeline outlining suspicious activity on the device alerted by Darktrace.

Case Study 2

The second case involved a customer within the Education sector. The affected device was also internet-facing, with network traffic indicating it was a WSUS server

Suspicious activity in this case once again began on October 24, notably only a few seconds after initial signs of compromise were observed in the first case. Initial anomalous behaviour also closely aligned, with outbound PowerShell connections to webhook[.]site, and then later connections, including HTTP POSTs, to the same endpoint with a cURL user agent.

While Darktrace did not observe any anomalous network activity on the device after October 24, the customer’s security integration resulted in an additional alert on October 27 for malicious activity, suggesting that the compromise may have continued locally.

By leveraging Darktrace’s security integrations, customers can investigate activity across different sources in a seamless manner, gaining additional insight and context to an attack.

A timeline outlining suspicious activity on the device alerted by Darktrace.
Figure 4: A timeline outlining suspicious activity on the device alerted by Darktrace.

Conclusion

Exploitation of a CVE can lead to a wide range of outcomes. In some cases, it may be limited to just a single device with a focused objective, such as exfiltration of sensitive data. In others, it could lead to lateral movement and a full network compromise, including ransomware deployment. As the threat of internet-facing exploitation continues to grow, security teams must be prepared to defend against such a possibility, regardless of the attack type or scale.

By focussing on detection of anomalous behaviour rather than relying on signatures associated with a specific CVE exploit, Darktrace is able to alert on post-exploitation activity regardless of the kind of behaviour seen. In addition, leveraging security integrations provides further context on activities beyond the visibility of Darktrace / NETWORKTM, enabling defenders to investigate and respond to attacks more effectively.

With adversaries weaponizing even trusted incident response tools, maintaining broad visibility and rapid response capabilities becomes critical to mitigating post-exploitation risk.

Credit to Emma Foulger (Global Threat Research Operations Lead), Tara Gould (Threat Research Lead), Eugene Chua (Principal Cyber Analyst & Analyst Team Lead), Nathaniel Jones (VP, Security & AI Strategy, Field CISO),

Edited by Ryan Traill (Analyst Content Lead)

Appendices

References

1.        https://nvd.nist.gov/vuln/detail/CVE-2025-59287

2.    https://www.bleepingcomputer.com/news/security/hackers-now-exploiting-critical-windows-server-wsus-flaw-in-attacks/

3.    https://learn.microsoft.com/en-us/windows-server/administration/windows-server-update-services/get-started/windows-server-update-services-wsus

4.    https://www.cisa.gov/news-events/alerts/2025/10/24/microsoft-releases-out-band-security-update-mitigate-windows-server-update-service-vulnerability-cve

5.    https://msrc.microsoft.com/update-guide/vulnerability/CVE-2025-59287

6.    https://thehackernews.com/2025/10/microsoft-issues-emergency-patch-for.html

7.    https://www.cisa.gov/known-exploited-vulnerabilities-catalog

8.    https://www.huntress.com/blog/exploitation-of-windows-server-update-services-remote-code-execution-vulnerability

9.    https://unit42.paloaltonetworks.com/microsoft-cve-2025-59287/

10. https://blog.talosintelligence.com/velociraptor-leveraged-in-ransomware-attacks/

11. https://github.com/hackirby/skuld

Darktrace Model Detections

·       Device / New PowerShell User Agent

·       Anomalous Connection / Powershell to Rare External

·       Compromise / Possible Tunnelling to Bin Services

·       Compromise / High Priority Tunnelling to Bin Services

·       Anomalous Server Activity / New User Agent from Internet Facing System

·       Device / New User Agent

·       Device / Internet Facing Device with High Priority Alert

·       Anomalous Connection / Multiple HTTP POSTs to Rare Hostname

·       Anomalous Server Activity / Rare External from Server

·       Compromise / Agent Beacon (Long Period)

·       Device / Large Number of Model Alerts

·       Compromise / Agent Beacon (Medium Period)

·       Device / Long Agent Connection to New Endpoint

·       Compromise / Slow Beaconing Activity To External Rare

·       Security Integration / Low Severity Integration Detection

·       Antigena / Network / Significant Anomaly / Antigena Alerts Over Time Block

·       Antigena / Network / Significant Anomaly / Antigena Enhanced Monitoring from Server Block

·       Antigena / Network / External Threat / Antigena Suspicious Activity Block

·       Antigena / Network / Significant Anomaly / Antigena Significant Server Anomaly Block

List of Indicators of Compromise (IoCs)

IoC - Type - Description + Confidence

o   royal-boat-bf05.qgtxtebl.workers[.]dev – Hostname – Likely C2 Infrastructure

o   royal-boat-bf05.qgtxtebl.workers[.]dev/v3.msi - URI – Likely payload

o   chat.hcqhajfv.workers[.]dev – Hostname – Possible C2 Infrastructure

o   185.69.24[.]18 – IP address – Possible C2 Infrastructure

o   185.69.24[.]18/bin.msi - URI – Likely payload

o   185.69.24[.]18/singapure - URI – Likely payload

The content provided in this blog is published by Darktrace for general informational purposes only and reflects our understanding of cybersecurity topics, trends, incidents, and developments at the time of publication. While we strive to ensure accuracy and relevance, the information is provided “as is” without any representations or warranties, express or implied. Darktrace makes no guarantees regarding the completeness, accuracy, reliability, or timeliness of any information presented and expressly disclaims all warranties.

Nothing in this blog constitutes legal, technical, or professional advice, and readers should consult qualified professionals before acting on any information contained herein. Any references to third-party organizations, technologies, threat actors, or incidents are for informational purposes only and do not imply affiliation, endorsement, or recommendation.

Darktrace, its affiliates, employees, or agents shall not be held liable for any loss, damage, or harm arising from the use of or reliance on the information in this blog.

The cybersecurity landscape evolves rapidly, and blog content may become outdated or superseded. We reserve the right to update, modify, or remove any content

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About the author
Emma Foulger
Global Threat Research Operations Lead

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October 24, 2025

Patch Smarter, Not Harder: Now Empowering Security Teams with Business-Aligned Threat Context Agents

Patch Smarter, Not Harder: Now Empowering Security Teams with Business-Aligned Threat Context Agents Default blog imageDefault blog image

Most risk management programs remain anchored in enumeration: scanning every asset, cataloging every CVE, and drowning in lists that rarely translate into action. Despite expensive scanners, annual pen tests, and countless spreadsheets, prioritization still falters at two critical points.

Context gaps at the device level: It’s hard to know which vulnerabilities actually matter to your business given existing privileges, what software it runs, and what controls already reduce risk.

Business translation: Even when the technical priority is clear, justifying effort and spend in financial terms—especially across many affected devices—can delay action. Especially if it means halting other areas of the business that directly generate revenue.

The result is familiar: alert fatigue, “too many highs,” and remediation that trails behind the threat landscape. Darktrace / Proactive Exposure Management addresses this by pairing precise, endpoint‑level context with clear, financial insight so teams can prioritize confidently and mobilize faster.

A powerful combination: No-Telemetry Endpoint Agent + Cost-Benefit Analysis

Darktrace / Proactive Exposure Management now uniquely combines technical precision with business clarity in a single workflow.  With this release, Darktrace / Proactive Exposure Management delivers a more holistic approach, uniting technical context and financial insight to drive proactive risk reduction. The result is a single solution that helps security teams stay ahead of threats while reducing noise, delays, and complexity.

  • No-Telemetry Endpoint: Collects installed software data and maps it to known CVEs—without network traffic—providing device-level vulnerability context and operational relevance.
  • Cost-Benefit Analysis for Patching: Calculates ROI by comparing patching effort with potential exploit impact, factoring in headcount time, device count, patch difficulty, and automation availability.

Introducing the No-Telemetry Endpoint Agent

Darktrace’s new endpoint agent inventories installed software on devices and maps it to known CVEs without collecting network data so you can prioritize using real device context and available security controls.

By grounding vulnerability findings in the reality of each endpoint, including its software footprint and existing controls, teams can cut through generic severity scores and focus on what matters most. The agent is ideal for remote devices, BYOD-adjacent fleets, or environments standardizing on Darktrace, and is available without additional licensing cost.

Darktrace / Proactive Exposure Management user interface
Figure 1: Darktrace / Proactive Exposure Management user interface

Built-In Cost-Benefit Analysis for Patching

Security teams often know what needs fixing but stakeholders need to understand why now. Darktrace’s new cost-benefit calculator compares the total cost to patch against the potential cost of exploit, producing an ROI for the patch action that expresses security action in clear financial terms.

Inputs like engineer time, number of affected devices, patch difficulty, and automation availability are factored in automatically. The result is a business-aligned justification for every patching decision—helping teams secure buy-in, accelerate approvals, and move work forward with one-click ticketing, CSV export, or risk acceptance.

Darktrace / Proactive Exposure Management Cost Benefit Analysis
Figure 2: Darktrace / Proactive Exposure Management Cost Benefit Analysis

A Smarter, Faster Approach to Exposure Management

Together, the no-telemetry endpoint and Cost–Benefit Analysis advance the CTEM motion from theory to practice. You gain higher‑fidelity discovery and validation signals at the device level, paired with business‑ready justification that accelerates mobilization. The result is fewer distractions, clearer priorities, and faster measurable risk reduction. This is not from chasing every alert, but by focusing on what moves the needle now.

  • Smarter Prioritization: Device‑level context trims noise and spotlights the exposures that matter for your business.
  • Faster Decisions: Built‑in ROI turns technical urgency into executive clarity—speeding approvals and action.
  • Practical Execution: Privacy‑conscious endpoint collection and ticketing/export options fit neatly into existing workflows.
  • Better Outcomes: Close the loop faster—discover, prioritize, validate, and mobilize—on the same operating surface.

Committed to innovation

These updates are part of the broader Darktrace release, which also included:

1. Major innovations in cloud security with the launch of the industry’s first fully automated cloud forensics solution, reinforcing Darktrace’s leadership in AI-native security.

2. Darktrace Network Endpoint eXtended Telemetry (NEXT) is revolutionizing NDR with the industry’s first mixed-telemetry agent using Self-Learning AI.

3. Improvements to our OT product, purpose built for industrial infrastructure, Darktrace / OT now brings dedicated OT dashboard, segmentation-aware risk modeling, and expanded visibility into edge assets and automation protocols.

Join our Live Launch Event

When? 

December 9, 2025

What will be covered?

Join our live broadcast to experience how Darktrace is eliminating blind spots for detection and response across your complete enterprise with new innovations in Agentic AI across our ActiveAI Security platform. Industry leaders from IDC will join Darktrace customers to discuss challenges in cross-domain security, with a live walkthrough reshaping the future of Network Detection & Response, Endpoint Detection & Response, Email Security, and SecOps in novel threat detection and autonomous investigations.

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About the author
Kelland Goodin
Product Marketing Specialist
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