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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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November 27, 2025

From Amazon to Louis Vuitton: How Darktrace Detects Black Friday Phishing Attacks

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Why Black Friday Drives a Surge in Phishing Attacks

In recent years, Black Friday has shifted from a single day of online retail sales and discounts to an extended ‘Black Friday Week’, often preceded by weeks of online hype. During this period, consumers are inundated with promotional emails and marketing campaigns as legitimate retailers compete for attention.

Unsurprisingly, this surge in legitimate communications creates an ideal environment for threat actors to launch targeted phishing campaigns designed to mimic legitimate retail emails. These campaigns often employ social engineering techniques that exploit urgency, exclusivity, and consumer trust in well-known brands, tactics designed to entice recipients into opening emails and clicking on malicious links.

Additionally, given the seasonal nature of Black Friday and the ever-changing habits of consumers, attackers adopt new tactics and register fresh domains each year, rather than reusing domains previously flagged as spam or phishing endpoints. While this may pose a challenge for traditional email security tools, it presents no such difficulty for Darktrace / EMAIL and its anomaly-based approach.

In the days and weeks leading up to ‘Black Friday’, Darktrace observed a spike in sophisticated phishing campaigns targeting consumers, demonstrating how attackers combine phycological manipulation with technical evasion to bypass basic security checks during this high-traffic period. This blog showcases several notable examples of highly convincing phishing emails detected and contained by Darktrace / EMAIL in mid to late November 2025.

Darktrace’s Black Friday Detections

Brand Impersonation: Deal Watchdogs’ Amazon Deals

The impersonation major online retailers has become a common tactic in retail-focused attacks, none more so than Amazon, which ranked as the fourth most impersonated brand in 2024, only behind Microsoft, Apple, Google, and Facebook [1]. Darktrace’s own research found Amazon to be the most mimicked brand, making up 80% of phishing attacks in its analysis of global consumer brands.

When faced with an email that appears to come from a trusted sender like Amazon, recipients are far more likely to engage, increasing the success rate of these phishing campaigns.

In one case observed on November 16, Darktrace detected an email with the subject line “NOW LIVE: Amazon’s Best Early Black Friday Deals on Gadgets Under $60”. The email was sent to a customer by the sender ‘Deal Watchdogs’, in what appeared to be an attempt to masquerade as a legitimate discount-finding platform. No evidence indicated that the company was legitimate. In fact, the threat actor made no attempt to create a convincing name, and the domain appeared to be generated by a domain generation algorithm (DGA), as shown in Figure 2.

Although the email was sent by ‘Deal Watchdogs’, it attempted to impersonate Amazon by featuring realistic branding, including the Amazon logo and a shade of orange similar to that used by them for the ‘CLICK HERE’ button and headline text.

Figure 1: The contents of the email observed by Darktrace, featuring authentic-looking Amazon branding.

Darktrace identified that the email, marked as urgent by the sender, contained a suspicious link to a Google storage endpoint (storage.googleapis[.]com), which had been hidden by the text “CLICK HERE”. If clicked, the link could have led to a credential harvester or served as a delivery vector for a malicious payload hosted on the Google storage platform.

Fortunately, Darktrace immediately identified the suspicious nature of this email and held it before delivery, preventing recipients from ever receiving or interacting with the malicious content.

Figure 2: Darktrace / EMAIL’s detection of the malicious phishing email sent to a customer.

Around the same time, Darktrace detected a similar email attempting to spoof Amazon on another customer’s network with the subject line “Our 10 Favorite Deals on Amazon That Started Today”, also sent by ‘Deal Watchdogs,’ suggesting a broader campaign.

Analysis revealed that this email originated from the domain petplatz[.]com, a fake marketing domain previously linked to spam activity according to open-source intelligence (OSINT) [2].

Brand Impersonation: Louis Vuitton

A few days later, on November 20, Darktrace / EMAIL detected a phishing email attempting to impersonate the luxury fashion brand Louis Vuitton. At first glance, the email, sent under the name ‘Louis Vuitton’ and titled “[Black Friday 2025] Discover Your New Favorite Louis Vuitton Bag – Elegance Starts Here”, appeared to be a legitimate Black Friday promotion. However, Darktrace’s analysis uncovered several red flags indicating a elaborate brand impersonation attempt.

The email was not sent by Louis Vuitton but by rskkqxyu@bookaaatop[.]ru, a Russia-based domain never before observed on the customer’s network. Darktrace flagged this as suspicious, noting that .ru domains were highly unusual for this recipient’s environment, further reinforcing the likelihood of malicious intent. Subsequent analysis revealed that the domain had only recently registered and was flagged as malicious by multiple OSINT sources [3].

Figure 3: Darktrace / EMAIL’s detection of the malicious email attempting to spoofLouis Vuitton, originating from a suspicious Russia-based domain.

Darktrace further noted that the email contained a highly suspicious link hidden behind the text “View Collection” and “Unsubscribe,” ensuring that any interaction, whether visiting the supposed ‘handbag store’ or attempting to opt out of marketing emails, would direct recipients to the same endpoint. The link resolved to xn--80aaae9btead2a[.]xn--p1ai (топааабоок[.]рф), a domain confirmed as malicious by multiple OSINT sources [4]. At the time of analysis, the domain was inaccessible, likely due to takedown efforts or the short-lived nature of the campaign.

Darktrace / EMAIL blocked this email before it reached customer inboxes, preventing recipients from interacting with the malicious content and averting any disruption.

Figure 4: The suspicious domain linked in the Louis Vuitton phishing email, now defunct.

Too good to be true?

Aside from spoofing well-known brands, threat actors frequently lure consumers with “too good to be true” luxury offers, a trend Darktrace observed in multiple cases throughout November.

In one instance, Darktrace identified an email with the subject line “[Black Friday 2025] Luxury Watches Starting at $250.” Emails contained a malicious phishing link, hidden behind text like “Rolex Starting from $250”, “Shop Now”, and “Unsubscribe”.

Figure 5: Example of a phishing email detected by Darktrace, containing malicious links concealed behind seemingly innocuous text.

Similarly to the Louis Vuitton email campaign described above, this malicious link led to a .ru domain (hxxps://x.wwwtopsalebooks[.]ru/.../d65fg4er[.]html), which had been flagged as malicious by multiple sources [5].

Figure 6: Darktrace / EMAIL’s detection of a malicious email promoting a fake luxury watch store, which was successfully held from recipient inboxes.

If accessed, this domain would redirect users to luxy-rox[.]com, a recently created domain (15 days old at the time of writing) that has also been flagged as malicious by OSINT sources [6]. When visited, the redirect domain displayed a convincing storefront advertising high-end watches at heavily discounted prices.

Figure 7: The fake storefront presented upon visiting the redirectdomain, luxy-rox[.]com.

Although the true intent of this domain could not be confirmed, it was likely a scam site or a credential-harvesting operation, as users were required to create an account to complete a purchase. As of the time or writing, the domain in no longer accessible .

This email illustrates a layered evasion tactic: attackers employed multiple domains, rapid domain registration, and concealed redirects to bypass detection. By leveraging luxury branding and urgency-driven discounts, the campaign sought to exploit seasonal shopping behaviors and entice victims into clicking.

Staying Protected During Seasonal Retail Scams

The investigation into these Black Friday-themed phishing emails highlights a clear trend: attackers are exploiting seasonal shopping events with highly convincing campaigns. Common tactics observed include brand impersonation (Amazon, Louis Vuitton, luxury watch brands), urgency-driven subject lines, and hidden malicious links often hosted on newly registered domains or cloud services.

These campaigns frequently use redirect chains, short-lived infrastructure, and psychological hooks like exclusivity and luxury appeal to bypass user scepticism and security filters. Organizations should remain vigilant during retail-heavy periods, reinforcing user awareness training, link inspection practices, and anomaly-based detection to mitigate these evolving threats.

Credit to Ryan Traill (Analyst Content Lead) and Owen Finn (Cyber Analyst)

Appendices

References

1.        https://keepnetlabs.com/blog/top-5-most-spoofed-brands-in-2024

2.        https://www.virustotal.com/gui/domain/petplatz.com

3.        https://www.virustotal.com/gui/domain/bookaaatop.ru

4.        https://www.virustotal.com/gui/domain/xn--80aaae9btead2a.xn--p1ai

5.        https://www.virustotal.com/gui/url/e2b868a74531cd779d8f4a0e1e610ec7f4efae7c29d8b8ab32c7a6740d770897?nocache=1

6.        https://www.virustotal.com/gui/domain/luxy-rox.com

Indicators of Compromise (IoCs)

IoC – Type – Description + Confidence

petplatz[.]com – Hostname – Spam domain

bookaaatop[.]ru – Hostname – Malicious Domain

xn--80aaae9btead2a[.]xn--p1ai (топааабоок[.]рф) – Hostname - Malicious Domain

hxxps://x.wwwtopsalebooks[.]ru/.../d65fg4er[.]html) – URL – Malicious Domain

luxy-rox[.]com – Hostname -  Malicious Domain

MITRE ATT&CK Mapping  

Tactic – Technique – Sub-Technique  

Initial Access - Phishing – (T1566)  

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About the author
Ryan Traill
Analyst Content Lead

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November 27, 2025

CastleLoader & CastleRAT: Behind TAG150’s Modular Malware Delivery System

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What is TAG-150?

TAG-150, a relatively new Malware-as-a-Service (MaaS) operator, has been active since March 2025, demonstrating rapid development and an expansive, evolving infrastructure designed to support its malicious operations. The group employs two custom malware families, CastleLoader and CastleRAT, to compromise target systems, with a primary focus on the United States [1]. TAG-150’s infrastructure included numerous victim-facing components, such as IP addresses and domains functioning as command-and-control (C2) servers associated with malware families like SecTopRAT and WarmCookie, in addition to CastleLoader and CastleRAT [2].

As of May 2025, CastleLoader alone had infected a reported 469 devices, underscoring the scale and sophistication of TAG-150’s campaign [1].

What are CastleLoader and CastleRAT?

CastleLoader is a loader malware, primarily designed to download and install additional malware, enabling chain infections across compromised systems [3]. TAG-150 employs a technique known as ClickFix, which uses deceptive domains that mimic document verification systems or browser update notifications to trick victims into executing malicious scripts. Furthermore, CastleLoader leverages fake GitHub repositories that impersonate legitimate tools as a distribution method, luring unsuspecting users into downloading and installing malware on their devices [4].

CastleRAT, meanwhile, is a remote access trojan (RAT) that serves as one of the primary payloads delivered by CastleLoader. Once deployed, CastleRAT grants attackers extensive control over the compromised system, enabling capabilities such as keylogging, screen capturing, and remote shell access.

TAG-150 leverages CastleLoader as its initial delivery mechanism, with CastleRAT acting as the main payload. This two-stage attack strategy enhances the resilience and effectiveness of their operations by separating the initial infection vector from the final payload deployment.

How are they deployed?

Castleloader uses code-obfuscation methods such as dead-code insertion and packing to hinder both static and dynamic analysis. After the payload is unpacked, it connects to its command-and-control server to retrieve and running additional, targeted components.

Its modular architecture enables it to function both as a delivery mechanism and a staging utility, allowing threat actors to decouple the initial infection from payload deployment. CastleLoader typically delivers its payloads as Portable Executables (PEs) containing embedded shellcode. This shellcode activates the loader’s core module, which then connects to the C2 server to retrieve and execute the next-stage malware.[6]

Following this, attackers deploy the ClickFix technique, impersonating legitimate software distribution platforms like Google Meet or browser update notifications. These deceptive sites trick victims into copying and executing PowerShell commands, thereby initiating the infection kill chain. [1]

When a user clicks on a spoofed Cloudflare “Verification Stepprompt, a background request is sent to a PHP script on the distribution domain (e.g., /s.php?an=0). The server’s response is then automatically copied to the user’s clipboard using the ‘unsecuredCopyToClipboard()’ function. [7].

The Python-based variant of CastleRAT, known as “PyNightShade,” has been engineered with stealth in mind, showing minimal detection across antivirus platforms [2]. As illustrated in Figure 1, PyNightShade communicates with the geolocation API service ip-api[.]com, demonstrating both request and response behavior

Packet Capture (PCAP) of PyNightShade, the Python-based variant of CastleRAT, communicating with the geolocation API service ip-api[.]com.
Figure 1: Packet Capture (PCAP) of PyNightShade, the Python-based variant of CastleRAT, communicating with the geolocation API service ip-api[.]com.

Darktrace Coverage

In mid-2025, Darktrace observed a range of anomalous activities across its customer base that appeared linked to CastleLoader, including the example below from a US based organization.

The activity began on June 26, when a device on the customer’s network was observed connecting to the IP address 173.44.141[.]89, a previously unseen IP for this network along with the use of multiple user agents, which was also rare for the user.  It was later determined that the IP address was a known indicator of compromise (IoC) associated with TAG-150’s CastleRAT and CastleLoader operations [2][5].

Figure 2: Darktrace’s detection of a device making unusual connections to the malicious endpoint 173.44.141[.]89.

The device was observed downloading two scripts from this endpoint, namely ‘/service/download/data_5x.bin’ and ‘/service/download/data_6x.bin’, which have both been linked to CastleLoader infections by open-source intelligence (OSINT) [8]. The archives contains embedded shellcode, which enables attackers to execute arbitrary code directly in memory, bypassing disk writes and making detection by endpoint detection and response (EDR) tools significantly more difficult [2].

 Darktrace’s detection of two scripts from the malicious endpoint.
Figure 3: Darktrace’s detection of two scripts from the malicious endpoint.

In addition to this, the affected device exhibited a high volume of internal connections to a broad range of endpoints, indicating potential scanning activity. Such behavior is often associated with reconnaissance efforts aimed at mapping internal infrastructure.

Darktrace / NETWORK correlated these behaviors and generated an Enhanced Monitoring model, a high-fidelity security model designed to detect activity consistent with the early stages of an attack. These high-priority models are continuously monitored and triaged by Darktrace’s Security Operations Center (SOC) as part of the Managed Threat Detection and Managed Detection & Response services, ensuring that subscribed customers are promptly alerted to emerging threats.

Darktrace detected an unusual ZIP file download alongside the anomalous script, followed by internal connectivity. This activity was correlated under an Enhanced Monitoring model.
Figure 4: Darktrace detected an unusual ZIP file download alongside the anomalous script, followed by internal connectivity. This activity was correlated under an Enhanced Monitoring model.

Darktrace Autonomous Response

Fortunately, Darktrace’s Autonomous Response capability was fully configured, enabling it to take immediate action against the offending device by blocking any further connections external to the malicious endpoint, 173.44.141[.]89. Additionally, Darktrace enforced a ‘group pattern of life’ on the device, restricting its behavior to match other devices in its peer group, ensuring it could not deviate from expected activity, while also blocking connections over 443, shutting down any unwanted internal scanning.

Figure 5: Actions performed by Darktrace’s Autonomous Response to contain the ongoing attack.

Conclusion

The rise of the MaaS ecosystem, coupled with attackers’ growing ability to customize tools and techniques for specific targets, is making intrusion prevention increasingly challenging for security teams. Many threat actors now leverage modular toolkits, dynamic infrastructure, and tailored payloads to evade static defenses and exploit even minor visibility gaps. In this instance, Darktrace demonstrated its capability to counter these evolving tactics by identifying early-stage attack chain behaviors such as network scanning and the initial infection attempt. Autonomous Response then blocked the CastleLoader IP delivering the malicious ZIP payload, halting the attack before escalation and protecting the organization from a potentially damaging multi-stage compromise

Credit to Ahmed Gardezi (Cyber Analyst) Tyler Rhea (Senior Cyber Analyst)
Edited by Ryan Traill (Analyst Content Lead)

Appendices

Darktrace Model Detections

  • Anomalous Connection / Unusual Internal Connections
  • Anomalous File / Zip or Gzip from Rare External Location
  • Anomalous File / Script from Rare External Location
  • Initial Attack Chain Activity (Enhanced Monitoring Model)

MITRE ATT&CK Mapping

  • T15588.001 - Resource Development – Malware
  • TG1599 – Defence Evasion – Network Boundary Bridging
  • T1046 – Discovery – Network Service Scanning
  • T1189 – Initial Access

List of IoCs
IoC - Type - Description + Confidence

  • 173.44.141[.]89 – IP – CastleLoader C2 Infrastructure
  • 173.44.141[.]89/service/download/data_5x.bin – URI – CastleLoader Script
  • 173.44.141[.]89/service/download/data_6x.bin – URI  - CastleLoader Script
  • wsc.zip – ZIP file – Possible Payload

References

[1] - https://blog.polyswarm.io/castleloader

[2] - https://www.recordedfuture.com/research/from-castleloader-to-castlerat-tag-150-advances-operations

[3] - https://www.pcrisk.com/removal-guides/34160-castleloader-malware

[4] - https://www.scworld.com/brief/malware-loader-castleloader-targets-devices-via-fake-github-clickfix-phishing

[5] https://www.virustotal.com/gui/ip-address/173.44.141.89/community

[6] https://thehackernews.com/2025/07/castleloader-malware-infects-469.html

[7] https://www.cryptika.com/new-castleloader-attack-using-cloudflare-themed-clickfix-technique-to-infect-windows-computers/

[8] https://www.cryptika.com/castlebot-malware-as-a-service-deploys-range-of-payloads-linked-to-ransomware-attacks/

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