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November 21, 2018

How Black Hats Take Advantage of Black Friday

The retail industry must be willing to adapt its cyber defenses against an ever-evolving adversary, or it may end Black Friday firmly in the red.
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
Justin Fier
SVP, Red Team Operations
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21
Nov 2018

From Thanksgiving to Cyber Monday, shoppers across the globe will splurge tens of billions of dollars on everything from pillows to parkas to Pokémon pajamas.

U.S. consumers alone spent a record $19.62 billion last Black Friday weekend — on just online purchases. And while the number of customers at brick-and-mortar stores declined 4% from 2016, e-commerce sales were 18% higher in 2017, when for the first time more Americans shopped online than in person. There is every reason to suspect that a virtually unprecedented volume of virtual cash is about to change hands, presenting an equally unprecedented opportunity for a massive holiday cyber-heist. Here’s what such a heist might look like:

Proof of concept

While the incentive for cyber-crime during this Black Friday weekend is historically unparalleled, it has long been the holiday of choice for criminals. On Cyber Monday of 2014, for instance, a DNS provider was hit by a relatively rudimentary DDoS attack that nonetheless disrupted its clients’ websites. More advanced DDoS attacks launched by modern Mirai botnets — like the 2016 Dyn attack that crippled many of the Internet’s top websites — would be devastating on Black Friday, when companies like Amazon reel in upwards of a million dollars per minute. And for smaller retailers, a ransomware or DDoS attack this weekend poses existential risk, both because of lost revenue and because of reputational damage in such a highly competitive industry.

Prior to last year’s Black Friday weekend, experts anticipated more than 50 million attacks on businesses during peak shopping days, and cyber-criminals did not disappoint. Darktrace detected a 70% uptick in significant threats facing its retail clients during the holiday season, from November and December, compared to the previous two months, an uptick that helps explain why cyber-crime cost the world $600 billion last year. At least in the short term, it appears that online crime does pay — especially after Thanksgiving.

Mode of attack

As forensics continue to improve and CCTVs rapidly proliferate, the in-person criminal heist has largely been replaced by online robbery, which leaves no fingerprints and can be seen by no camera. One example: the annual amount of money stolen in U.S. bank robberies — the quintessential heist — has fallen by more than 60% since 2003, while cyber-crimes like credit card fraud have simultaneously skyrocketed. This transition to digital larceny makes financial sense as well, given that less than 10% of the world’s currency still exists as physical cash.

Indeed, identity theft is even more lucrative than bank robbery if done at scale, yet it entails far less risk for the perpetrators. Stolen credit card numbers can each sell for $100 on the Dark Web, rendering crimes like the Target breach — which took place during Black Friday weekend in 2013 and exposed 40 million debit and credit accounts — extremely profitable. With more than 100 million Americans and close to a billion global shoppers online during the holiday season, ’tis certainly the season for a large-scale assault on personal information.

But perhaps the most revolutionary aspect of cyber-heists is that they need not even steal anything to make off with loot. Faced with a well-timed ransomware attack, retailers often simply hand over their cash to remain operational: 70% of businesses paid the ransom after attacks in 2016, prompting criminals to quadruple their average demand. And on the busiest shopping day in history, there’s no telling how exorbitant these demands might be.

Cyber-threats that are specifically aimed at the retail sector make the challenge of security even more difficult for defenders, since much like a targeted traditional heist, they exploit their victims’ unique vulnerabilities. The numbers validate common sense here: insights from across Darktrace’s customer base reveal that these key retail threats — which include personalized phishing attacks, Cloud and SaaS attacks, as well as trojans — are more than twice as likely to become high-priority incidents as the average threat. With so much money on the line, every retailer should expect to confront targeted attacks throughout the weekend.

Bypassing the defenses

From ransomware to data exfiltration, one can make an educated guess about the kinds of threats facing retailers this Black Friday. But the truth is that no one knows exactly what the next global cyber-attack will look like, particularly given the enormous incentive for criminals to create an entirely new attack strain — or even a new type of attack altogether. Several recent, state-sponsored exploits have proven that the financial and technical backing exists to produce malware sophisticated enough to deliver a serious blow to the U.S. economy.

Innovative attacks pose a fundamental problem for traditional security tools, which rely on knowledge of past incidents to stop future ones. By updating their predefined notions of what constitutes a cyber-threat when a breach occurs, the best of these tools stop previously known attacks, but they are nonetheless blind to unknown threats. Many retailers have deployed Darktrace’s AI cyber security because it doesn’t presume to know what tomorrow’s attack will look like; rather, Darktrace learns on the job to differentiate between normal and abnormal behavior. But while such adaptive security is the only approach that stands a chance in today’s fast-changing threat landscape, most retailers have yet to make the switch.

In this era of DNA forensics and near-ubiquitous surveillance, the criminal heist has not disappeared — it’s digitized. And while retail companies prepare themselves for the generic cyber-threats of the past, very few are in a position to counter a never-before-seen attack that, like a physical heist, has been planned for months to exploit their unique security blind spots. As we inch closer to zero hour, the industry must be willing to adapt its cyber defenses against an ever-evolving adversary, or it may end Black Friday firmly in the red.

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
Justin Fier
SVP, Red Team Operations

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December 22, 2025

The Year Ahead: AI Cybersecurity Trends to Watch in 2026

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Introduction: 2026 cyber trends

Each year, we ask some of our experts to step back from the day-to-day pace of incidents, vulnerabilities, and headlines to reflect on the forces reshaping the threat landscape. The goal is simple:  to identify and share the trends we believe will matter most in the year ahead, based on the real-world challenges our customers are facing, the technology and issues our R&D teams are exploring, and our observations of how both attackers and defenders are adapting.  

In 2025, we saw generative AI and early agentic systems moving from limited pilots into more widespread adoption across enterprises. Generative AI tools became embedded in SaaS products and enterprise workflows we rely on every day, AI agents gained more access to data and systems, and we saw glimpses of how threat actors can manipulate commercial AI models for attacks. At the same time, expanding cloud and SaaS ecosystems and the increasing use of automation continued to stretch traditional security assumptions.

Looking ahead to 2026, we’re already seeing the security of AI models, agents, and the identities that power them becoming a key point of tension – and opportunity -- for both attackers and defenders. Long-standing challenges and risks such as identity, trust, data integrity, and human decision-making will not disappear, but AI and automation will increase the speed and scale of the cyber risk.  

Here's what a few of our experts believe are the trends that will shape this next phase of cybersecurity, and the realities organizations should prepare for.  

Agentic AI is the next big insider risk

In 2026, organizations may experience their first large-scale security incidents driven by agentic AI behaving in unintended ways—not necessarily due to malicious intent, but because of how easily agents can be influenced. AI agents are designed to be helpful, lack judgment, and operate without understanding context or consequence. This makes them highly efficient—and highly pliable. Unlike human insiders, agentic systems do not need to be socially engineered, coerced, or bribed. They only need to be prompted creatively, misinterpret legitimate prompts, or be vulnerable to indirect prompt injection. Without strong controls around access, scope, and behavior, agents may over-share data, misroute communications, or take actions that introduce real business risk. Securing AI adoption will increasingly depend on treating agents as first-class identities—monitored, constrained, and evaluated based on behavior, not intent.

-- Nicole Carignan, SVP of Security & AI Strategy

Prompt Injection moves from theory to front-page breach

We’ll see the first major story of an indirect prompt injection attack against companies adopting AI either through an accessible chatbot or an agentic system ingesting a hidden prompt. In practice, this may result in unauthorized data exposure or unintended malicious behavior by AI systems, such as over-sharing information, misrouting communications, or acting outside their intended scope. Recent attention on this risk—particularly in the context of AI-powered browsers and additional safety layers being introduced to guide agent behavior—highlights a growing industry awareness of the challenge.  

-- Collin Chapleau, Senior Director of Security & AI Strategy

Humans are even more outpaced, but not broken

When it comes to cyber, people aren’t failing; the system is moving faster than they can. Attackers exploit the gap between human judgment and machine-speed operations. The rise of deepfakes and emotion-driven scams that we’ve seen in the last few years reduce our ability to spot the familiar human cues we’ve been taught to look out for. Fraud now spans social platforms, encrypted chat, and instant payments in minutes. Expecting humans to be the last line of defense is unrealistic.

Defense must assume human fallibility and design accordingly. Automated provenance checks, cryptographic signatures, and dual-channel verification should precede human judgment. Training still matters, but it cannot close the gap alone. In the year ahead, we need to see more of a focus on partnership: systems that absorb risk so humans make decisions in context, not under pressure.

-- Margaret Cunningham, VP of Security & AI Strategy

AI removes the attacker bottleneck—smaller organizations feel the impact

One factor that is currently preventing more companies from breaches is a bottleneck on the attacker side: there’s not enough human hacker capital. The number of human hands on a keyboard is a rate-determining factor in the threat landscape. Further advancements of AI and automation will continue to open that bottleneck. We are already seeing that. The ostrich approach of hoping that one’s own company is too obscure to be noticed by attackers will no longer work as attacker capacity increases.  

-- Max Heinemeyer, Global Field CISO

SaaS platforms become the preferred supply chain target

Attackers have learned a simple lesson: compromising SaaS platforms can have big payouts. As a result, we’ll see more targeting of commercial off-the-shelf SaaS providers, which are often highly trusted and deeply integrated into business environments. Some of these attacks may involve software with unfamiliar brand names, but their downstream impact will be significant. In 2026, expect more breaches where attackers leverage valid credentials, APIs, or misconfigurations to bypass traditional defenses entirely.

-- Nathaniel Jones, VP of Security & AI Strategy

Increased commercialization of generative AI and AI assistants in cyber attacks

One trend we’re watching closely for 2026 is the commercialization of AI-assisted cybercrime. For example, cybercrime prompt playbooks sold on the dark web—essentially copy-and-paste frameworks that show attackers how to misuse or jailbreak AI models. It’s an evolution of what we saw in 2025, where AI lowered the barrier to entry. In 2026, those techniques become productized, scalable, and much easier to reuse.  

-- Toby Lewis, Global Head of Threat Analysis

Conclusion

Taken together, these trends underscore that the core challenges of cybersecurity are not changing dramatically -- identity, trust, data, and human decision-making still sit at the core of most incidents. What is changing quickly is the environment in which these challenges play out. AI and automation are accelerating everything: how quickly attackers can scale, how widely risk is distributed, and how easily unintended behavior can create real impact. And as technology like cloud services and SaaS platforms become even more deeply integrated into businesses, the potential attack surface continues to expand.  

Predictions are not guarantees. But the patterns emerging today suggest that 2026 will be a year where securing AI becomes inseparable from securing the business itself. The organizations that prepare now—by understanding how AI is used, how it behaves, and how it can be misused—will be best positioned to adopt these technologies with confidence in the year ahead.

Learn more about how to secure AI adoption in the enterprise without compromise by registering to join our live launch webinar on February 3, 2026.  

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December 22, 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.

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About the author
Carlos Gray
Senior Product Marketing Manager, Email
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