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April 1, 2023

Cyber Security Threats - Email Compromise With Generative AI

Discover how generative AI is impacting email attacks and what companies can do to prepare for more sophisticated and targeted attacker campaigns.
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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01
Apr 2023

Email communications in the era of generative AI

Today’s headlines on cyber security attacks are dominated by serious breaches that cripple critical national infrastructure providers, wreak geopolitical havoc through nation state espionage, and create paralyzing financial demands through extortion and ransomware. But how do these breaches occur in the first place, and why do they keep happening?

Social engineering – specifically malicious cyber campaigns delivered via email - remain the primary source of an organization’s vulnerability to attack. A recent survey conducted by Darktrace to 6,700 global cross-industry professionals across the UK, US, Australia, France, Germany, and Netherlands, found almost a third (30%) have fallen victim to a fraudulent email. The risk, as ever, seems to be uncontrollably on the rise – 70% of respondents have noticed an increase in the frequency of malicious emails in the last six months. 

At the end of last year, I wrote about how widespread accessibility to generative AI has compounded the problem, leading to likely efficiency gains for skilled threat actors launching email attacks. Just a few weeks ago, we published research which demonstrated that while the number of email attacks across our own customer base has remained steady since ChatGPT’s release, those that rely on tricking victims into clicking malicious links have declined, while linguistic complexity, including text volume, punctuation, and sentence length among others, have increased. This indicates that cyber-criminals may be redirecting their focus to crafting more sophisticated social engineering scams that exploit user trust delivered over email. 

Our latest findings, conducted by Darktrace Research, today reveal a 135% increase in ‘novel social engineering attacks’ across thousands of active Darktrace/Email customers from January to February 2023, corresponding with the widespread adoption of ChatGPT. A novel social engineering phishing email is an email attack that shows a strong linguistic deviation – semantically and syntactically – compared to other phishing emails. The trend suggests that generative AI, such as ChatGPT, is providing an avenue for threat actors to craft sophisticated and targeted attacks at speed and scale.

Organizations are already well aware of the danger novel threats pose – globally, 82% of respondents reported are concerned that hackers can use generative AI to create scam emails that are indistinguishable from genuine communication.

Navigating the trust deficit 

Employees are being exploited continuously through their primary means of communication - email. Given that humans, and our psychology, are at the heart of the problem, organizations have scrambled to develop awareness and training programs that are delivered routinely to employees in an attempt to help them defend themselves and their organization. While a defense-in-depth approach is generally a good practice to follow, the value of security awareness training, teaching employees to spot attempts at social engineering delivered in text format, is diminishing rapidly. This problem has become especially evident now that we find ourselves in a world where ‘bad’ emails look all but undistinguishable to the human eye from ‘good’ emails. 

Over emphasizing the responsibility of employees poses a business challenge as well as a security problem: a bloated trust deficit. In times of economic uncertainty, business success is predicated on employee productivity, creativity, and efficiency. All three of these are squashed when employees treat the communication they receive, both internal and external, with forensic suspicion and mistrust. 

As generative AI becomes more mainstream – across images, audio, video, and text – we anticipate that this erosion of trust in digital communication will only continue. What happens to the workplace if an employee is left questioning their own perception when communicating with their manager or a colleague, who they can see and hear over a video conference call, but who may be an entirely fictitious creation?

The way forward

The future lies in a partnership between artificial intelligence and human beings where the algorithms are responsible for determining whether communication is malicious or benign, thereby taking the burden of responsibility off the human. In turn, humans can pursue activities that drive productivity and performance. Current training and awareness programs, coupled with traditional email security technologies which assume that knowledge of past attacks will help predict campaigns, are not sustainable in this rapidly evolving landscape. 

Our research reveals that traditional email security tools that rely on knowledge of past threats, take an average of thirteen days from an attack being launched on a victim to that attack being detected. This leaves defenders vulnerable for almost two weeks if they rely solely on traditional tools. When this statistic is contextualized against the 135% increase we’ve seen in novel social engineering campaigns, the inefficiency of ‘attack centric’ email security is made perfectly evident. If we don’t know how to define entirely new and unique attacks, how can we ever hope to recognize them based on past attacks? 

A deep understanding of ‘you’ is needed in the face of these radical changes to the email threat landscape. Instead of trying to predict attacks, an understanding of your employees’ behavior, based from their email inbox, is needed to create patterns of life for every email user: their relationships, tone and sentiments and hundreds of other data points. By leveraging AI to combat email security threats, we not only reduce risk, but revitalize organizational trusts and contribute to business outcomes.

Ironically, generative AI may be worsening the social engineering challenge, but AI that knows you, could be the parry. 

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 2, 2025

Protecting the Experience: How a global hospitality brand stays resilient with Darktrace

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For the Global Chief Technology Officer (CTO) of a leading experiential leisure provider, security is mission critical to protecting a business built on reputation, digital innovation, and guest experience. The company operates large-scale immersive venues across the UK and US, blending activity-driven hospitality with premium dining and vibrant spaces designed for hundreds of guests. With a lean, centrally managed IT team responsible for securing locations worldwide, the challenge is balancing robust cybersecurity with operational efficiency and customer experience.

Brand buzz attracts attention – and attacks

Mid-sized, fast-growing hospitality organizations face a unique risk profile. When systems go down in a venue, the impact is immediate: hundreds of disrupted guest experiences, lost revenue during peak hours, and potential long-term reputation damage. Each time the organization opened a new venue, the surge of marketing buzz attracted attention in local markets and waves of sophisticated cyberattacks, including:

Phishing campaigns leveraging brand momentum to lure employees into clicking on malicious links.

AI-enhanced impersonation using advanced techniques to create AI-generated video calls and deep-researched, contextualized emails  

Fake domains targeting leadership with AI-generated messages that contained insider context gleaned from public information.

“Our endpoint security and antivirus tools were powerless against these sophisticated AI-powered campaigns. We didn’t want to manage incidents anymore. We wanted to prevent them from ever happening.”  - Global CTO

Proactive, preventative security with Darktrace AI

The company’s cybersecurity vision was clear: “Proactive, preventative – that was our mandate,” said the CTO. With a lean and busy IT group, the business evaluated several security solutions using deep-dive workshops. Darktrace proved the best fit for supporting the organization’s proactive mindset, offering:

  • Autonomy without added headcount: Darktrace provided powerful AI-driven detection and autonomous response functions with minimal manual oversight required.
  • Modular adoption: The company could start with core email and network protection and expand into cloud and endpoint coverage, aligning spend with growth.
  • Partnership and responsiveness: “We wanted people we trust, respect, and know will show up when we need them. Darktrace did just that,” said the CTO.
  • Affordability at scale: Darktrace offered reasonable upfront costs plus predictable, sustainable economics as the company and IT infrastructure expanded.  

“The combination of AI capabilities, a scalable model, and a strong engagement team tipped the balance in Darktrace’s favor, and we have not been disappointed,” said the CTO.

Phased deployment builds trust

To minimize disruption to critical hospitality systems like global Point of Sales (POS) terminals and Audio-Visual (AV) infrastructure, deployment was phased:

  1. Observation and human-led response: Initially, Darktrace was deployed in detection-only mode. Alerts were manually reviewed.
  2. Incremental autonomous response: Darktrace Autonomous Response was enabled on select models, taking action on low-risk scenarios. Higher-risk subnets and devices remained under human control.
  3. Full autonomous coverage: With tuning and reinforcement, autonomous response was expanded across domains, trusted to take decisive action in real time. Analysts retained the ability to review and contextualize incidents.

“Darktrace managed the rollout through detailed, professional, and responsive project management – ensuring a smooth, successful adoption and creating a standardized cybersecurity playbook for future venue launches,” said the CTO.  

AI delivers the outcomes that matter  

Measurable efficiency replaces endless alerts

Darktrace autonomous response significantly decreased false alerts and noise. “If it’s quiet, we’re confident there isn’t a problem,” said the CTO. Within six months, Darktrace conducted 3,599 total investigations, detected and contained 320 incidents indicative of an attack, resolved 91% of those events autonomously, and escalated only 9% to human analysts. The efficiency gains were enormous, saving analysts 740 hours on investigations within a single month.  

Precision AI turns inbox chaos into calm

Darktrace Self-Learning AI modeled sender/recipient norms, content/linguistic baselines, and communication patterns unique to the organization’s launch cadence, resulting in:

  • Automated holds and neutralizations of anomalous executive-style messages
  • Rapid detection of novel templates and tone shifts that deviated from the organization’s lived email graph, even when indicators were not yet on any feed
  • Downstream reduction in help-desk escalations tied to suspicious email

Full visibility fuels real-time response

Darktrace gives IT direct visibility without extra licensing, and it surfaces ground truth across every venue, including:

  • Device geolocation and placement drift: Darktrace exposed devices and users operating outside approved zones, prompting new segmentation and access-control policies.
  • Guest Wi-Fi realities: Darktrace AI uncovered high-risk activity on guest networks, like crypto-mining and dark-web traffic, driving stricter VLAN separation and access hygiene.
  • Lateral-movement containment: Autonomous response fenced suspicious activity in real time, buying time for human investigation while keeping POS and AV systems unaffected.

Smarter endpoints for a smarter network

Endpoints once relied on static agents effective only against known signatures. Darktrace’s behavioral models now detect subtle anomalies at the endpoint process level that EDRs often miss, such as misuse of legitimate applications (commonly used in living-off-the-land attacks), unapproved application usage and policy violations. This increases the accuracy and fidelity of network-based investigations by adding endpoint process context alongside existing EDR alerts.

Autonomous response for continuous compliance

Across PCI, GDPR, and cross-border privacy obligations, Darktrace’s native evidencing is helping the team demonstrate control rather than merely assert it:

  • Asset and flow awareness: Knowing “what is where” and “who talks to what” underpins PCI scoping and data-flow diagrams.
  • Layered safeguards: Showing autonomous prevention, network segmentation, and rapid containment supports risk registers and control attestations.
  • Audit-ready artifacts: Investigations and autonomous actions produce artifacts that “tick the box” without additional tooling.  

Defining the next era of resilience with AI

With rapid global expansion underway, the company is using its cybersecurity playbook to streamline and secure future venue launches. In the near term, IT is focused on strengthening prevention, using Darktrace insights to guide new policy updates and infrastructure changes like imposing stricter guest-network posture and refining venue device baselines.

For tech leaders charting their path to proactive cyber defense, the CTO stresses success won’t come from sidestepping AI, but from turning it into a core capability.

“AI isn’t optional – it’s operational. The real risk to your business is trying to out-scale automated adversaries with human speed alone. When applied to the right use case, AI becomes a catalyst for efficiency, resilience, and business growth.” - Global CTO
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December 2, 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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