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August 4, 2020

How to Prevent Spear Phishing Attacks Post Twitter Hack

Twitter confirmed spear phishing as the cause of last month's attack. Learn about the limits of current defenses against spear phishing and how AI can stop it.
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
Dan Fein
VP, Product
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04
Aug 2020

Twitter has now confirmed that it was a “phone spear phishing attack” targeting a small number of their employees that allowed hackers to access 130 high-profile user accounts and fool thousands of people into giving away money via bitcoin.

Spear phishing involves targeted texts or emails aimed at individuals in an attempt to ‘hook’ them into opening an attachment or malicious link. This attack highlights the limitations in the security controls adopted by even some of the largest and most tech-savvy organizations out there, who continue to fall victim to this well-known attack technique.

The incident has been described by Twitter as a “coordinated social engineering attack” that “successfully targeted employees with access to internal systems and tools.”

Though the specific nature of the attack remains unclear, it likely followed a similar pattern to the series of threat finds detailed elsewhere on the Darktrace Blog: impersonating trusted colleagues or platforms, such as WeTransfer, Microsoft Teams or even Twitter itself, with an urgent message coaxing an employee into clicking on a disguised URL and inputting their credentials on a fake login page.

When an employee inputs their credentials, that data is recorded and beaconed back to the attacker, who will then use these login details to access internal systems — which, in this case, allowed them to subsequently take control of celebrities’ Twitter accounts and send out the damaging Tweets that left thousands out of pocket.

Training the workforce is not enough

Twitter says in a statement that this incident has forced them to “accelerate several of [their] pre-existing security workstreams.” But the suggestion that they will continue to organize “ongoing company-wide phishing exercises throughout the year” indicates an over-reliance on the ability of humans to identify these malicious email attacks that are getting more and more advanced, and harder to distinguish from genuine communication.

Cyber-criminals are now using AI to create fake profiles, personalize messages and replicate communication patterns, at a speed and scale that no human ever could. In this threat landscape, there can no longer be a reliance solely on educating the workforce, as the difference between a malicious email and legitimate communication becomes almost imperceptible. This has led to an acceptance that we must rely on technology to help us catch the subtle signs of attack, when humans alone fail to do so.

The legacy approach: no playbook for new attacks

The majority of communications security systems are not where they need to be, and this is particularly true for the email realm. Most tools in use today rely on static blacklists of rules and signatures that analyze emails in isolation, against known ‘bads’. Methods like looking for IP addresses or file hashes associated with phishing have had limited success in stopping attackers, who have devised simple techniques to bypass them.

As we have explored previously, attackers are constantly changing their approach, purchasing new domains en masse, experimenting with novel strains of malware, and manipulating headers to get around common validation checks. It is due to these developments that Secure Email Gateways (SEGs) become antiquated almost the moment they are updated.

The mean lifetime of an attack has reduced from 2.1 days in 2018 to 0.5 days in 2020. As soon as an SEG identifies a domain or a file hash as malicious, cyber-criminals change their attack infrastructure and launch a new wave of fresh attacks. Their fundamental means of operation renders legacy security tools incapable of evolving with the threat landscape, and it is for this reason that over 94% of cyber-attacks today start with an email.

How Cyber AI catches the threats others miss

However, one area where email security has seen great progress even in the last two years is the application of AI to spot the subtle features of advanced email attacks, even those that leverage novel malware. This approach allows security tools to move away from the binary decision-making that comes with asking “Is this email ‘bad’?” and moving to the far more useful question of “does this belong?”

This form of what we’re calling ‘layered AI’ combines supervised and unsupervised machine learning, enabling it to spot the subtle deviations from learned ‘patterns of life’ that are indicative of a cyber-threat.

Supervised machine learning models can be trained on millions of emails to find subtle patterns undetectable by humans and detect new variations of known threat types. These models are able to find the real-world intentions behind an email: by training on millions of spear phishing emails, for example, a system can find patterns associated with this type of email attack and accurately classify a future email as spear phishing.

In addition, unsupervised machine learning models can be trained on all available email data for an organization to find unknown variations of unknown threat types — that is, the ‘unknown unknowns,’ the combinations never before seen. Ultimately this is what enables a system to ask that critical question “does this belong?” and spot genuine anomalies that fall outside of the norm.

Layering both of these applications of AI allows us to make determinations such as: ‘this is a phishing email and it doesn’t belong’, dramatically improving the system’s accuracy and allowing it to interrupt only the malicious emails – since there could be phishy-looking emails that are legitimate! It also enables us to act in proportion to the threat identified: locking links and attachments in some cases, or holding back emails entirely in others.

This form of ‘layered AI’ requires an advanced understanding of mathematics and machine learning that takes years of research and development. With that experience, Cyber AI has proven itself capable of catching the full range of advanced attacks targeting the inbox, from spear phishing and impersonation attempts, to account takeovers and supply chain attacks. Once implemented, it takes only a week before any new organization can derive value, and thousands of customers now rely on Cyber AI to protect both their email realm and wider network.

Plenty more phish in the sea

This will not be the last time this year that a cyber-attack caused by spear phishing makes the headlines. Just this week, it was revealed that Russian-backed cyber-criminals stole sensitive documents on US-UK trade talks after successful spear phishing, and the technique may well have played a part in ongoing vaccine research espionage that surfaced in July.

With the US presidential race heating up, it was recently revealed that fewer than 3 out of 10 election administrators have basic controls to prevent phishing. This attack method may come to not only damage organizations and their reputation, but also to undermine the trust that serves as the bedrock of democracy. Now is the time to start recognizing the very real threat that email attackers represent, and to prepare our defenses accordingly.

Learn more about AI email security

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
Dan Fein
VP, Product

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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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