How to Detect AI Spear Phishing That Uses OSINT

AI-powered phishing is reshaping cybersecurity as everyone knows it. Deepfakes, data poisoning, and prompt injection aren’t future risks. They’re active threats today.

Among the most dangerous types of phishing attacks is spear phishing, which is highly personalized with open-source intelligence (OSINT). Hyper-targeted campaigns mimic internal communications, reference company events, and use multiple channels to trick even well-trained employees.

The combination of AI phishing and OSINT-driven targeting now results in attacks with higher success rates than traditional phishing. Higher success rates mean more data breaches that compromise sensitive data and lead to costly damage.

How has spear phishing evolved, and what specific spear phishing threats do organizations now face? Can situation-based training help build the human firewall needed to improve spear phishing detection and defense?

Indeed, a successful framework requires the right AI capabilities, such as those provided by top platforms. But some tools fulfill only certain cybersecurity needs, while others meet different requirements. 

None, however, offer an end-to-end experience that closely resembles Adaptive Security’s next-generation platform, which addresses security awareness training, phishing simulations, and even phishing triage.

What is Spear Phishing?

Spear phishing is a type of phishing attack that targets a specific individual, role, or organization using personal context, insider references, or social engineering.

Unlike general phishing, which casts a wide net, spear phishing is designed to feel legitimate by referencing accurate details about the recipient.

AI has supercharged spear phishing, with platforms like ChatGPT generating error-free emails that impersonate real colleagues.

Combined with OSINT, such as LinkedIn profile data, press releases, or leaked credentials, spear phishing attacks feel authentic and arrive at exactly the wrong time. Whether delivered by email, voice, or video, spear phishing now leverages real context to build false trust.

Just how effective is spear phishing using OSINT? In 2023, spear phishing emails made up less than 0.1% of all emails sent, but they were responsible for 66% of all breaches.

For risk management and prevention, organizations must prioritize security awareness training with phishing simulations that reflect how attacks actually unfold.

AI-OSINT Convergence: How Attackers Weaponize Public Data

Spear phishing succeeds by exploiting what an organization publicly shares about employees, clients, culture, and operations. With the help of AI, attackers process and personalize this information faster than ever before.

Social media intelligence gathering

Cybercriminals utilize social media to create detailed profiles of their targets. LinkedIn is often the first stop, as it reveals titles, recent promotions, team hierarchies, and strategic changes. X, formerly Twitter, and Instagram add personal context, such as event attendance, travel plans, or current locations.

Using this data, attackers craft spear phishing communications that appear timely and relevant:

• “Hey Taylor, per your post about onboarding a new vendor…”
• “Quick approval request before you head to Black Hat USA…”

Corporate website data mining

Attackers scrape press releases, blog content, and leadership biographies to simulate insider knowledge. When an email references a real product launch or mimics the writing style of a CEO, it’s easier to trust, especially under pressure.

What type of data mining can AI tools do?

• Generate spoofed onboarding requests for new hires.
• Impersonate vendors using names from actual partner lists.
• Match communication tone from on-site blog posts.

Leaked database correlation

Attackers correlate OSINT with breached datasets to boost credibility. Password dumps, credential leaks, or customer relationship management (CRM) exports allow them to pair names with emails, Slack handles, or personal addresses.

Adaptive Security’s phishing training for employees mirrors the exact conditions described, teaching a workforce to recognize that even harmless-looking data can be weaponized in targeted phishing attacks.

Why AI Makes Spear Phishing Harder to Detect

AI doesn’t just generate content. It generates realistic content.

With perfect grammar and visuals, contextually aware phrasing, and natural tone, AI-powered spear phishing easily evades technical filters and deceives cautious targets.

Linguistic patterns that evade filters

Traditional filters look for misspellings or strange phrasing.  AI spear phishing avoids these triggers by:

• Mimicking corporate writing styles
• Avoiding overt red flags, such as odd links or requests
• Generating tailored calls-to-action that feel familiar

Even cybersecurity professionals admit that some AI-crafted emails are nearly indistinguishable from genuine internal messages.

Behavioral anomalies

While the language may pass technical inspection, behavior often tells a different story. AI spear phishing attacks might:

• Arrive outside standard communication windows
• Request urgent actions, like wire transfers or credentials
• Mimic personas who rarely communicate with the recipient directly

Training users to identify contextual inconsistencies, such as odd timing or unfamiliar tone, dramatically increases detection rates.

Adaptive Security’s training modules emphasize the subtle behavioral cues through interactive feedback, helping employees build pattern recognition over time.

Simulation-Based Training Improves Spear Phishing Detection

While technical defenses like endpoint security are essential for combating cyberattacks, a human firewall remains the strongest defense layer against spear phishing.

So, what’s the best way to improve human recognition? Simulation-based training that mirrors the sophistication of real-world attacks.

Phishing simulations drive detection in three distinct ways:

• Repetition Builds Pattern Recognition: Just like in sports or medicine, exposure to realistic practice conditions creates muscle memory.
• Mistake-Driven Learning Improves Memory: When users fall for a simulation, they immediately receive context-aware feedback on what they missed.
• Role-Based Realism Increases Vigilance: Simulations tailored to executives, finance, HR, or IT reflect the types of spear phishing most likely to target those roles.

Unlike legacy solutions that focus on checkbox compliance training, Adaptive Security delivers custom simulations based on real-world, multi-channel attacks. Whether the threat comes via email, voice, video, or SMS, employees learn to spot spear phishing in the environments where they’re bound to encounter it.

Training-based detection enhancements in spear phishing defense

Multi-Channel Spear Phishing: Email is Just the Beginning

Spear phishing doesn’t stop at email. Cybercriminals now use a mix of communication channels to increase trust and urgency, especially in high-value scams.

Voice clones and vishing scenarios

Attackers can clone a voice with just a few seconds of audio, and finance teams are increasingly targeted with voice-based spear phishing, where a fake senior leader or colleague requests immediate action or approval.

Clues to listen for include:

• Slight robotic tone or timing
• Overuse of formal phrasing
• References to real company events pulled from OSINT

Deepfake video attacks

Among the most high-stakes spear phishing attacks are those that use deepfake video calls or pre-recorded videos. Such scams are particularly dangerous in remote-friendly companies where video conferences replace in-person meetings.

In one case, attackers used a deepfake to impersonate several colleagues, leading to a $25 million loss at Arup.

Adaptive Security’s platform offers mult-channel phishing simulations, allowing teams to train against more than email-based phishing attacks alone.

Stronger Human Firewall, Better Detection Rates

What separates successful spear phishing defense from repeated data breaches? IT and security teams that treat training as an integral part of their security posture, rather than just a compliance measure.

When employees are prepared to spot personalized phishing:

• Reporting rate increases
• Response time shrinks
• Incidents are escalated faster, before damage ever occurs

Adaptive Security constructs this human firewall using AI-powered security awareness training, customized by role, channel, and performance.

See, detection isn’t only technical. It’s human, and training is how the human firewall is activated.

Comparing Detection Platforms for AI Spear Phishing

When evaluating security awareness training platforms to defend against AI-powered spear phishing, consider features beyond basic ones such as email filtering and compliance checklists.

The most effective platforms simulate targeted attacks using OSINT, train employees across multiple channels, and adapt to changing threat patterns.

Here’s a breakdown of how leading platforms compare, based on the ability to prepare organizations for AI spear phishing.

Adaptive Security

Adaptive Security is purpose-built to protect against spear phishing and all other types of AI-powered phishing attacks that threaten organizations globally.

Unlike platforms that focus narrowly on email phishing or offer static training modules, Adaptive Security delivers dynamic, role-based training that reflects real-world attacks, including deepfakes, smishing, vishing, and other emerging threats.

• Offers customized spear phishing simulations based on open-source intelligence
• Trains across email, voice, video, and SMS channels for comprehensive preparation
• Includes behavioral AI analytics to monitor risk and adapt training in real time

KnowBe4

KnowBe4 is a well-established solution in security awareness training, offering a sizable content library and robust compliance features. However, its training is primarily email-centric, and there’s limited support for spear phishing vectors, such as deepfakes.

• Provides email phishing simulations with varying difficulty levels
• Offers basic reporting on user susceptibility and campaign results

Mimecast

Mimecast’s training platform is tightly integrated with the company’s email security products. While useful for organizations already in the ecosystem, it doesn’t offer in-depth phishing simulations for spear phishing techniques beyond traditional vectors.

• Integrates email training with Mimecast threat intelligence
• Uses short, entertaining videos to drive engagement

HoxHunt

HoxHunt utilizes gamification to foster employee engagement in phishing awareness. It excels at email simulations and personalized learning paths.

• Delivers adaptive email phishing campaigns based on user behavior
• Encourages positive behavior through points and game-like progression

Infosec IQ

Infosec IQ offers a highly customizable training library and strong support for compliance-driven learning paths. It’s ideal for organizations seeking control over training content.

• Allows administrators to create and tailor custom training programs
• Covers a wide range of cybersecurity topics, including compliance

Train for the Attacks You’ll Actually Face

AI spear phishing isn’t a theory; it’s one of the fastest-growing forms of targeted cybercrime.

Attackers are faster, smarter, and more persuasive than ever before. Your best defense? Well, it’s not more filtering. It’s training employees to spot the subtle, personalized signs that AI-powered threats leave behind.

Through fully customizable, real-world phishing simulations, Adaptive Security trains your employees to detect what machines can’t and builds the human firewall that cybersecurity depends on.